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Airbnb Key West: Top Rentals for a Dream Tropical Vacation

If the wanderlust within you is itching for a destination where you can soak up the sun in style, Key West may be one of the top beach locations that come to mind. But this isn’t your usual tourist traps; the Conch Republic delivers unique, chic, and extra bougie experiences that would make you want to have a vacation encore—or stay in the island for good.

With an array of luxe Airbnb and short-term rental gems, you’re not just staying in Key West; you’re living it. These properties boast amenities that seem straight out of a Vanity Fair magazine: infinity pools overlooking crystal-clear waters, private docks where the ocean is your backyard, and outdoor entertainment spaces where the sunset is part of your guest list.

You might find yourself in a luxe minimalist modern condo where the smart tech would impress even the most tech-averse. Or perhaps a swanky beach house where the birds of paradise would serenade you as you enjoy a dip in your own private pool.

These amenities and more make these places more than just somewhere to drop your bags as you run off to the sun and sand or to crash after a night of hardcore island partying—they’re your golden ticket to tasting the island life like royalty. Whether it’s sipping a crafted cocktail by your private pool or waking up to the soft sounds of the sea, every moment is meticulously designed to ensure unparalleled satisfaction.

So, grab your squad, pack that SPF, and get ready to embrace island time—celebrity style.
Are you ready to experience living the life of the rich and famous in Key West? Let’s dig in!

An introduction to Key West, Florida

Watch this video to uncover the absolute must-do experiences in Key West, Florida – trust me, you won’t want to miss out on these unforgettable adventures!

Visit Mallory Square (0:13) – Bar Hopping on Duval Street (0:53) – Learn How Rum is Made (1:52) – Take an Unforgettable Ride on a Floating Tiki Bar (2:29) – Lounge On One of Key West’s Gorgeous Beaches (2:51) – Harry S. Truman Little White House (3:46) – Visit the Southernmost Point in the Mainland U.S. (4:25) – Take a Relaxing Day Trip to the Dry Tortugas (4:45) – Take a Boat Tour of Key West (5:25) – Key West Lighthouse and Keeper’s Quarters (6:00) – Ernest Hemingway Home and Museum (6:37) – Other Famous Residents (7:12)

Our selection of rental properties

Click any of the images below to view the property directly

Private Sanctuary Near Duval Street In Key West

Secret Villa II

Location: Key West, Florida

Photo Credit: VRBO

Entire home/apt

6 Guests

3 Bedrooms

3 Bathrooms

Secret Villa II, nestled just a block from the life of the party—Duval Street, is the kind of spot where luxury kicks back with its feet up, sipping on a margarita. Fresh off a recent glow-up, this 3BR, 3BA home is the vacation escape of your dreams.

Step outside, and bam, you’re in the mix of it all – food, tunes, the paradise vibes. But step back inside and you’ve got yourself a lush hideout where you’ll forget the world outside with its serene and chill ambiance. This place has got the works. We’re talking about a private pool that’s heated (because why not?), wrapped in a tropical hug of greenery so lush, you’ll forget you’re a stone’s throw from the action. Inside, it’s all about space and grace.

The rooms are spacious and chic, and upstairs, two master suites serve serious sleep goals—one with a California King bed. Go big or go home, right? Plus, a shared balcony is perfect for stargazing or just catching those Key West breezes.

Parking’s tight, sure; there’s only room for one. But who’s driving when you’re this close to everything? Plus, they’ve got a plan for the extra wheels, five minutes away.

And because you’re royalty here, there’s a 24-hour concierge. Day or night, they’ve got you. So, whether you’re here for the Key West classic hits or just to kick it poolside in peace, Secret Villa II’s where it’s at.

From the owner:

Secret Villa II is a newly renovated, private sanctuary, centrally located off of Duval Street with your very own private pool.

Secret Villa II is just one block from Key West’s most famous party area – Duval Street. Enjoy the hustle and bustle of live music and world renowned restaurants. Then you and your party can retire to your private sanctuary.

If you are looking for additional accommodations our sister property Secret Villa I is available in the neighboring compound.

Secret Villa II is the perfect vacation rental for discerning, upscale clientele. The property is a newly renovated 3BR, 3BA home with a heated pool situated in the heart of old town on a quiet and private lane. The fenced-in private pool is surrounded by lush gardens, natural vegetation, and tropical canopies, providing our guests with the privacy and intimacy that Key West visitors are looking for. All rooms are large and comfortable making the house a perfect getaway for up to 3 couples. The 2nd floor has two master bedrooms each with an en suite bathroom – one with a California King bed and the other with a King bed. The upstairs bedrooms share a large outside porch where guests can enjoy a late night glass of wine while watching the night sky and taking in a cool evening breeze. The first floor bedroom shares a bathroom with the living room and comes furnished with a Queen sized bed.

Please note – parking is limited to one vehicle no larger than a mid-sized car or small SUV. Paid parking is available in a public lot 5 minutes away for additional vehicles.

Guests are greeted upon arrival to the property. We provide 24 hour concierge service.

The property is located one block from Duval Street. Key West is a bike friendly island. We have bicycles available for rent as well as a golf cart. Please contact us for additional information.

Guest Reviews For This Rental

The Secret Villa II in Key West, Florida, is a treasure for guests looking for a blend of privacy, comfort, and proximity to local attractions. This newly renovated 3-bedroom, 3-bathroom home has won the hearts of many, boasting an impressive overall rating of 4.97 out of 5 stars from 72 reviews.

The villa’s standout features include a private, heated pool nestled within lush gardens and a location just a block away from the lively Duval Street, offering guests a unique experience of solitude and social entertainment.

Here’s what you need to know, based on guest reviews:

  • Cleanliness: 5.0/5 – Received a perfect score, indicating that guests were extremely satisfied with the cleanliness of the villa.
  • Accuracy: 5.0/5 – guests found the villa’s description and amenities accurately represented in the listing.
  • Communication: 5.0/5 – The host’s responsiveness and communication were top-notch, reflected in another flawless perfect-star rating.
  • Location: 5.0/5 – The villa’s location earned a perfect score, with guests loving its convenience and proximity to Key West’s main attractions.
  • Value: 4.8/5 – The value for the experience provided at the villa was highly regarded.

Guest reviews highlighted the villa’s prime location, close to everything yet offering a secluded feel. The host was praised for being very responsive, enhancing the overall experience.

Guests have had great times, appreciating the well-maintained property, the added bonus of bicycles, and the private and charming atmosphere of Jim’s home. Communication with Jim and the caretakers was smooth, addressing any issues promptly, making guests feel well taken care of.

This villa, with its comfortable bedrooms, wonderful pool area, and patio, is a highly recommended stay in Key West, especially for those seeking a mix of excitement and tranquility.

Getting The Best Deal

Just stumbled upon Secret Villa II on Airbnb and was ready to book my Key West escape. But wait, before I hit confirm, I decided to give HiChee a whirl. Lo and behold, it showed me a twin deal on VRBO that could save me an extra $1,118! Same villa, same dates, same chill vibes. Can’t beat that kind of secret savings!

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Near Duval Street With Historic Charm And Pool

Casa De Cuba

Location: Key West, Florida

Photo Credit: Airbnb

Entire home/apt

6 Guests

3 Bedrooms

2 Bathrooms

Next on our list is the Casa de Cuba, an ultra bougie home that sits a stone’s throw from the buzz of Duval Street, yet feels worlds apart. Right in Key West’s heart, where tales of old mingle with the pulse of the now, this spot’s got more layers than your favorite beach read. Picture a pad where the vibe’s as rich as its history, nestled by the historic Gato Cigar factory—yep, that’s the one with the cigar museum. And with Duval Square just across the way, your foodie finds and retail therapy are sorted.

When it comes to the interiors, this property is a masterclass in blending comfort with cool. Decked out in shades that soothe and pop, it’s like walking into a live Pinterest board. From plush lounges perfect for deep chats or deeper naps to a sunroom that’s all about those lazy morning vibes, Casa de Cuba knows luxury isn’t just about the threads count.

Each bedroom’s a retreat, with the main boasting a spa vibe in its ensuite that’s begging for long soaks. Out back, the pool’s set for all-day lounging, with enough bench space to debate the best Key West eats as you dip.

And with bikes and a golf cart on standby, exploring Key West becomes your personalized adventure. And with the crew on call 24/7, every whim’s covered, from the best dive spots to where to catch that Key West sunset.

From the owner:

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can’t be beat. The home’s history is rich; neighboring the historic Gato Cigar factory which is now restored and used as county offices, but still houses a small cigar museum. Duval Square is directly across the street with three restaurants, shops, a nail salon and convenience store. And why not start

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can’t be beat. The home’s history is rich; neighboring the historic Gato Cigar factory which is now restored and used as county offices, but still houses a small cigar museum. Duval Square is directly across the street with three restaurants, shops, a nail salon and convenience store. And why not start or finish the day with the best homemade ice cream in Key West at Flamingo’s Crossing, just down at the corner!

Casa de Cuba is beautifully decorated with soothing colors, sophisticated furnishings, accented with Cuban and beach themed artwork. There’s both a living room and additional sitting area in the front of the house. Pass through the dining room to the cottage style kitchen with black granite counters, open to the sun room with large farmhouse table with French windows and doors overlooking the pool and a indoor/outdoor room to enjoy the tropical lifestyle of Key West.

The main bedroom is beautifully decorated with its black pencil post king bed, soft green color palette and unique bathroom with spa style and nice step-in shower. The twin bedroom sits off the living room in the front of the house. The third bedroom sits to the back of the house and feels like a second master suite with French doors to the outdoor sitting area and pool area. The second bath with tub is adjacent to the third bedroom and accessible to all guests. The 21′ long heat optional pool features benches on each side for relaxing a little longer There is an outdoor table and nearby gas grill for outside/open air dining. Additional amenities include WIFI, security alarm, stereo, flat panel televisions, washer and dryer.

Guest Reviews For This Rental

Casa de Cuba stands out as a beacon of elegance, style, and convenience in Key West, Florida. With its unparalleled location just half a block from Duval Street in the historic district, this beautiful home offers guests the perfect combination of luxury and practicality. Casa de Cuba has earned a stellar 5.0 rating, showcasing its exceptional quality and guest satisfaction.

Here’s what you need to know, based on guest reviews:

  • Cleanliness: 5.0/5 – Guests universally praise the impeccable cleanliness of the home.
  • Accuracy: 5.0/5 – The property’s description and amenities are as perfect in reality as they are listed online.
  • Communication: 5.0/5 – The host’s communication is top-notch, also earning a perfect score.
  • Location: 5.0/5 – Its location is unbeatable, meriting a perfect rating. Just a short walk from the heart of Key West, guests love the convenience.
  • Value: 4.8/5 – Scoring slightly lower but still impressive. Guests feel they get great worth for their expenditure.

In their reviews, guests highlighted various aspects of their stay, from the unbeatable location to the amazing amenities. The property seems to cater exceptionally well to families, with comments praising its suitability for both children and adults. The private pool is a hit for cooling off during hot days, and the home’s proximity to major landmarks and local flavors like Flamingo’s Crossing’s homemade ice cream adds to its charm. One guest encapsulated the experience, stating, “We loved, loved, loved our house at 518 Virginia! It was absolutely perfect!”

Casa de Cuba is celebrated not just for its physical attributes but also for the experiences it provides. Whether it’s the ease of communication with the host, the spotless and stylish accommodations, or the unbeatable location near Duval Street, guests leave with lasting memories. If you’re seeking a place where elegance meets comfort in Key West, Casa de Cuba might just be your next vacation destination.

Getting The Best Deal

Casa de Cuba on Airbnb looked perfect for our Key West adventure. But, before sealing the deal, gave HiChee a try. Lo and behold, by copying the Airbnb code and inputting it into HiChee, found out VRBO had it for $2,662 cheaper. Score!

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Key West Luxury With Private Pool

Villa Josine

Location: Key West, Florida

Photo Credit: Airbnb

Entire home/apt

8 Guests

4 Bedrooms

4.5 Bathrooms

Tucked just a quick stroll from the pulsing energy of Duval Street, there’s a Key West hideaway that’s redefining the vacation destination scene. It’s a spot where luxury isn’t just an option—it’s the whole mood. With open spaces that invite the outside in, it’s all about those chill vibes and upscale living.

This place rocks an open-plan vibe on the main floor, where living, dining, and cooking merge seamlessly. The kitchen is all about the milk and honey—sporting quartz countertops and stainless steel everything. It’s the kind of space that makes you want to cook, even if your usual idea of meal prep is choosing the right takeout.

The kitchen isn’t the only area that smells like a million bucks: each lavish bedroom has its own ensuite because waiting to take a shower is nobody’s idea of a good time. Decked out with luxe beds and chic décor, these rooms are where dreams—and epic nap sessions—happen.

Out back, the pool area is a private paradise. Surrounded by lush greenery, it’s the perfect spot for lazy afternoons or that golden hour selfie. And when the sun dips, this outdoor oasis transforms into the ultimate chill-out zone, complete with al fresco dining under the stars.

From the owner:

Upscale elegance describes this two-story home just 2 blocks from Duval Street and close to shops and restaurants. The first floor’s open concept coupled with 4 ensuite baths, allows you room to enjoy your guests and your privacy in this spacious home.

THE PROPERTY: Villa Josine not only has curb appeal but also is a stunning example of a Key West eyebrow house. This architectural style was popular in the 1800’s and helped keep the second story cool, prior to the advent of air-conditioning. Unlike those of the 1800’s, this home has been completely renovated with modern amenities and high-end designer finishes. It’s large enough for your entire family to enjoy.

There are 4 spacious bedrooms with 4 ensuite baths. Located on the first floor are two of the bedrooms, one with a king bed and the other with two twin beds. This sleeping area would be ideal for a young family or older family members. Two additional bedrooms are located on the second floor, one with a king bed and the other with a queen bed. All bedrooms include TVs and ceiling fans and are brilliantly furnished, such that you may not want to leave your room. There is also a convenient half bath on the first floor.

The main area on the first floor includes a grand, vaulted ceiling and a large, open concept living room/dining room and kitchen. Top of the line stainless steel appliances, white quartz counter tops and open shelving will allure your family’s chef to create sumptuous meals, even while on vacation. The kitchen is adorned with a large island with seating for four and is cleverly trimmed in historic Dade County pine. An additional dining area overlooks the back of the home and private pool via a wall of glass doors.

Step outside onto the spacious, comfortably furnished covered deck. You can spend time reading, relaxing, or chilling in the pool. Surrounded by lush landscaping, you will feel as if you are in a private wonderland.

Beautiful furnishings and natural light abound throughout this home. Nooks and crannies, eclectic art and Key West charm are elegantly highlighted in this unique and exquisite home. Come stay a while in Villa Josine!

Guest Reviews For This Rental

Villa Josine, a large designer home located in Key West, Florida, has garnered unanimous praise from its guests, securing a perfect 5.0 rating. This spacious abode not only boasts an upscale elegance but also sits merely 2 blocks from Duval Street, close to various shops and restaurants, making it an ideal location for visitors.

Here’s what you need to know, based on guest reviews:

  • Cleanliness: 5.0/5 – Guests consistently noted the impeccable cleanliness of the home.
  • Accuracy: 4.9/5 – The villa’s representation through photos and descriptions was found to be nearly perfect, with guests feeling their expectations were met upon arrival.
  • Communication: 5.0/5 – The management’s responsiveness and helpful communication were highlighted as exceptional.
  • Location: 5.0/5 – The convenience and appeal of the villa’s location received top marks, with 100% of recent guests awarding it 5 stars.
  • Value: 4.9/5 – Guests felt that the experience offered great value, reflecting the quality and amenities relative to the cost.

The sentiment across reviews is overwhelmingly positive. For instance, Mandy from Henrico, Virginia, commended the beautiful home and its excellent location, noting the perfect condition of the rooms, veranda, and pool area. Abbey, visiting from Chapel Hill, North Carolina, praised the great location and the amazing pool, recommending the villa for a memorable stay in Key West. Christopher, hailing from Copenhagen, Denmark, admired the charm and cleanliness of the house, deeming it ideal for larger groups or families.

In essence, Villa Josine is cherished for its elegant design, prime location, and comprehensive amenities, making it one of the most loved homes on Airbnb. The meticulous attention to detail in every aspect of the stay, from the initial communication to the final check-out, underscores the villa’s exceptional quality and the management’s commitment to guest satisfaction.

Getting The Best Deal

Imagine an open-plan Key West hideaway, oozing luxury vibes. Found it on Airbnb, but before sealing the deal, HiChee led me to VRBO with a sweet $1,688 saving! Who knew? Same dates, same guests, just more savings for that sunset cocktail fund!

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Beach Home In Marathon With Private Dock

Grassy Key

Location: Marathon, Florida

Photo Credit: Airbnb

Entire home/apt

4 Guests

2 Bedrooms

2 Bathrooms

Next is this luxe beach hideout that’s miles away from the ordinary. Here, the vibe is exclusive yet totally Key West, blending serene nature with top-tier amenities. Think gourmet kitchen where culinary magic happens, luxe linens that whisper “best sleep ever,” and a private pool hugged by a lush tropical garden that’s straight-up paradise vibes.

Their real flex, however, is A 300′ private pier that lets you dive deep into the ocean’s embrace, complete with a fish cleaning station for those catch-of-the-day moments. It doesn’t get any fresher than that, yes? It’s like having your own slice of the ocean, minus the crowds.

Surrounded by a garden that’s a green thumb’s dream, the private pool is the chill spot for sunset toasts or dipping your toes. And those towering coconut palms are picture-perfect but mind the falling coconuts!

Dining out is just a hop, skip, and jump away, but with a kitchen as swanky as this, staying in is the new going out. And when it’s time to hit the hay, those fluffy towels and bathrobes make winding down a luxe experience.

So, if your vacay mood board includes luxe living with a side of tropical bliss, this Grassy Key gem is where you hit “book now” and start planning your escape.

From the owner:

You don’t come to the islands to stay in a town! Relax in our tropical paradise beach home away from the traffic and noise of US Hwy #1.

The perfect location has now been turned into the perfect oasis. Special features include a gourmet kitchen, private pool surrounded by lush landscaping, private 300′ pier/dock with a fish cleaning station. Our guests enjoy luxury bedding with quality linens, fluffy towels and bathrobes. Wireless internet service and cable tv.

On Grassy Key we are close enough to enjoy Marathon restaurants and grocery shopping yet still be able to explore dive sites in both the Upper and Lower Keys!

When we decided to purchase a home in the Florida Keys privacy and being close to nature was top on our list of requirements. We found the perfect combination on Grassy Key, a small island between Islamorada and Marathon made famous by ‘Flipper’ and the Dolphin Research Center.

After a full day in the sun there is no better place to relax than in the cool fresh water pool surrounded by the lush gardens. Check out the massive coconut and royal palms, the 9′ high bird of paradise, the banana and key lime trees, blooming hibiscus and orchids. Just don’t lay under the coconut trees!

Located in a quiet Grassy Key neighborhood with nature at your doorstep. Enjoy biking the nearby Overseas Heritage Trail, exploring the Dolphin Research Center, or dining at nearby restaurants.

Guest Reviews For This Rental

The guest reviews for the Beach House with a Private Pool & Dock, overlooking the Gulf for sunsets in Marathon, Florida, are overwhelmingly positive, reflecting a near-perfect guest experience. This property has earned an impressive overall rating of 4.97 out of 5 stars across 32 reviews, indicating consistent satisfaction among visitors.

Here’s what you need to know, based on guest reviews:

  • Cleanliness: 5.0/5 – Guests appreciate the immaculate condition of both the interior and exterior spaces.
  • Accuracy: 5.0/5 – Visitors found the listing’s description and photos accurately represent the actual experience and amenities of the property.
  • Communication: 5.0/5 – The host’s responsiveness and ability to effectively communicate with guests are highlighted.
  • Location: 5.0/5 – The location is highly praised for its serene setting away from traffic and noise, providing a tranquil escape with nature at the doorstep.
  • Value: 4.8/5 – The property’s value for the price paid received a slightly lower, yet still excellent, indicating most guests feel their stay was worth the investment.

Guest reviews convey a strong sense of satisfaction, with many highlighting the private and peaceful environment, the property’s cleanliness, and the host’s excellent communication. The convenient location, despite being secluded, allows easy access to nearby amenities and attractions, making it a preferred choice for those looking to explore the Keys while having a comfortable and quiet base to return to. The property seems to offer a blend of relaxation with its private pool and lush landscaping, and adventure with its private pier/dock, appealing to a wide range of visitors seeking a memorable stay in the Florida Keys.

Getting The Best Deal

Step up your vacation game with this luxe beach retreat on VRBO. But wait, don’t hit “book” just yet! By pasting the code into HiChee and tweaking the details to match, I discovered a secret deal on Airbnb that saves you $1,238. That’s more cash for fruity cocktails by the pool!

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Stunning Luxury Airbnb In Marathon, Key West

Off the Hook

Location: Marathon, Florida

Photo Credit: Airbnb

Entire home/apt

8 Guests

3 Bedrooms

3 Bathrooms

Off the Hook is a place where the luxury of modern living blends seamlessly with the chill, laid-back atmosphere of the Florida Keys, a.k.a. the Conch Republic. In Marathon, you’re smack in the middle of island life, with 20 keys to explore and adventures at every turn.

This pad is ultra-modern, boasting all the amenities you’d want for a legit escape from the real world. Floor-to-ceiling glass doors flood the space with natural light, making every selfie Insta-worthy. Bedrooms are more than just a place to crash; they’re mini-retreats within your retreat, complete with queen beds that are like sleeping on a cloud and TVs for Netflix binges.

Foodies, get psyched. The kitchen in this joint is straight-up gourmet, decked out with Viking appliances and surrounded by views that’ll have you cooking with a side of awe. And when you’re ready to dine al fresco, there’s no better spot than your own outdoor dining area.

But let’s be real, the outdoor scene is where it’s at. Picture yourself lounging by your private pool, the size of a small apartment (440 sq ft, to be exact), or chilling by the fire pit on your own sandy slice of paradise. The outdoor bar and grill? Prime for serving up the day’s catch.

Boat owners, we didn’t forget you. Dock yours at the house and hit the ocean whenever the mood strikes. Coming back to grill your catch and jump into the pool is the day’s perfect finale.

And because we know Fido is part of the fam, this place is pet-friendly. So, pack your bags (and your pup), and get ready to experience the Keys like never before.

From the owner:

Rooftop Lounge area with breathtaking views of sparkling water.

Off the Hook

Picture spending your vacation in this gorgeous, custom-built modern pool home, this is the place where you will make memories that will last a lifetime!

Only an hours’ drive south of the continental United States you will find Marathon, in the Florida Keys, an island a world apart from the fast pace of big city life. If you have ever dreamed of staying in a Florida Keys Vacation Rental this home will exceed your expectations.

The beaches, diving, and fishing in the Florida Keys are among the best in the world. Spend your day relaxing on the beach, worry-free. The Florida Keys are 125 miles of the most beautiful islands in the whole world. You will feel like you left the United States and are visiting a Caribbean Island. Within this strand of islands is the city of Marathon. Marathon is made up of 20 Keys, and is the heart of the Florida Keys. Marathon is a tropical getaway for the whole family.

Off the Hook is a beautiful, newly built, home located right on the edge of Marathon. As you enter this Florida Keys vacation home you walk into the gorgeous foyer with floor-to-ceiling windows and extra-large glass doors that let you enjoy the beautiful outdoors even when inside. Off the Hook has two guest bedrooms on the first floor one on each side of the huge custom bathroom, both bedrooms include queen beds, along with ottoman-to-twin beds, large TVs, and tons of natural light. On the second floor of this incredible home you will find, a top-of-the-line kitchen with Viking appliances, tons of counter space, and endless views from the floor-to-ceiling windows providing a 180° view of the surrounding area, a perfect place to make delicious meals to enjoy in the outdoor dining area. As well as, The master bedroom which includes an ensuite bathroom and an incredible oversized rainfall shower, a king bed, and a private balcony overlooking the glittering canal,

While the inside of this home is beautiful the outdoors is the real reason to come to this luxury Keys vacation home. The outdoor space in this home is like your own private retreat. Featuring an expansive custom swimming pool, a cozy fire pit surrounded by warm, soft sand like you’re on your own private beach, and a top-of-the-line outdoor bar with a gas grill where you can cook all of your fresh catch from the day. The fully fenced in yard provides privacy while you are relaxing in paradise. Catch the sunset on your private rooftop lounge area with unobstructed views as the sun sinks into the Gulf of Mexico each evening.

Bringing your own boat? Imagine having your boat docked right behind your home and heading out to the open Atlantic Ocean is just a short 10-minute boat drive. Picture coming back to your home, cleaning your catch right on the dock, throwing it on the grill in your state-of-the-art outdoor kitchen area, grabbing a drink at the outdoor bar, and then jumping in the pool to cool off while your dinner is cooking just steps away. All this, and more, is possible at Off the Hook.

Guest Reviews For This Rental

Nestled in the serene landscapes of Marathon, Florida, “Off the Hook” emerges as a modern, exclusive, and luxuriously appointed pool home, capturing the hearts of visitors with its blend of comfort, elegance, and a multitude of high-end amenities. This haven, highly rated at 5.0 stars based on 15 glowing reviews, offers a quintessential vacation experience in the heart of the Florida Keys.

Here’s what you need to know, based on guest reviews:

  • Cleanliness: 4.9/5 – Guests consistently laud the immaculate condition of the home. Its well-maintained spaces, both indoors and outdoors, evidently meet and exceed the expectations of discerning travelers.
  • Accuracy: 5.0/5 – “Off the Hook” stands true to its descriptions and images, ensuring guests encounter no surprises but delightful realizations of their expectations.
  • Communication: 5.0/5 – Highlights the responsive and helpful nature of the host, making every guest feel valued and supported throughout their stay.
  • Location: 5.0/5 – The strategic and scenic location offers breathtaking views and convenient access to local attractions, ensuring a blend of tranquility and adventure.
  • Value: 4.9/5 – The value for money is evident in the comprehensive amenities, luxurious details, and unique experiences provided, making every dollar spent wholly worthwhile.

Visitors find themselves enveloped in a world of luxury and relaxation, from the expansive custom swimming pool and cozy fire pit to the state-of-the-art outdoor bar and grill. The inclusion of high-end appliances, kayaks, bicycles, and a saltwater swimming pool underscores the home’s commitment to providing an unparalleled vacation experience. Guests appreciate the thoughtful amenities, including a well-stocked kitchen and comfortable beds with high-quality linens, contributing to the overall exceptional stay.

Whether it’s lounging by the pool, exploring the surroundings on a kayak, or enjoying the sunset from the rooftop lounge area, “Off the Hook” caters to a wide array of preferences and activities. The dock, ideal for fishing or manatee visits, adds an element of adventure and connection with nature.

Getting The Best Deal

Craving a taste of island life in Marathon? Look no further than VRBO‘s “Off the Hook.” This stylish retreat boasts floor-to-ceiling windows, gourmet kitchen, and a private pool that screams relaxation. Plus, it’s pet-friendly! But here’s the scoop: HiChee helped me snag an extra $694 off my booking through Airbnb.

And with another click of the “Magic search” button, unveils more savings for me. This website helped me pocket another $2,383!

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Luxe Airbnb Oasis Near Duval Street

Secret Villa I

Location: Key West, Florida

Photo Credit: Airbnb

Entire home/apt

6 Guests

3 Bedrooms

3 Bathrooms

Secret Villa again? Yes, we also liked the encore, but nothing beats the OG. This is the Key West hideout you’ve been dreaming of but didn’t know existed. One block off the legendary Duval Street, this spot is the ultimate “close-but-not-too-close” to the island’s non-stop party vibe. After hitting the town, you can ghost the crowd and return to your luxe oasis.

Newly done-up, this 3BR, 3BA gem serves major home-away-from-home vibes, but with a twist of Key West flair. It’s got space for three couples to crash without cramping anyone’s style. Upstairs, the two main bedrooms are kitted out with beds you’ll want to sink into – one California King and another King – and both come with those en-suite setups that make you feel like you’re at a spa. The shared balcony? Pure gold for late-night wind-downs or early morning “where’s my coffee?” moments.

Outside is a gorgeous private pool, because Key West heat demands a dip, surrounded by green that’s more secret garden than backyard. And if you’re here to explore, Duval Street’s just a block away. We’re talking easy access to the heart of Key West’s shindigs without stumbling too far from your serene hideout.

Oh, and if you’re rolling deep or just need extra space, Secret Villa II is right next door. Parking’s tight, so pack light or park it like a pro in nearby spots. They’ve got you with a 24-hour concierge, because questions don’t keep office hours. And for cruising around the island? Hit them up for bike rentals.

From the owner:

Secret Villa I is a newly renovated, private sanctuary, centrally located off of Duval Street with your very own private pool.

Secret Villa I is just one block from Key West’s most famous party area – Duval Street. Enjoy the hustle and bustle of live music and world renowned restaurants. Then you and your party can retire to your private sanctuary.

If you are looking for additional accommodations our sister property Secret Villa II is available in the neighboring compound.

Secret Villa I is the perfect vacation rental for discerning, upscale clientele. The property is a newly renovated 3BR, 3BA home with a heated pool situated in the heart of old town on a quiet and private lane. The fenced-in private pool is surrounded by lush gardens, natural vegetation, and tropical canopies, providing our guests with the privacy and intimacy that Key West visitors are looking for.

All rooms are large and comfortable making the house a perfect getaway for up to 3 couples. The 2nd floor has two master bedrooms each with an en suite bathroom – one with a California King bed and the other with a King bed. The upstairs bedrooms share a large outside porch where guests can enjoy a late night glass of wine while watching the night sky and taking in a cool evening breeze. The first floor bedroom shares a bathroom with the living room and comes furnished with a Queen sized bed.

Please note – parking is limited to one vehicle no larger than a mid-sized car or small SUV. Paid parking is available in a public lot 5 minutes away for additional vehicles.

Guests are greeted upon arrival to the property. We provide 24 hour concierge service.

Duval Street

The property is located one block from Duval Street. Key West is a bike friendly island. We have bicycles available for rent. Please contact us for additional information.

Key West is great

Guest Reviews For This Rental

Secret Villa I, nestled in Key West, Florida, emerges as a newly renovated oasis, lauded with an impressive 4.97 rating out of 5 from 60 reviews. Its allure is not just in its luxurious accommodations but also in its strategic location, merely a block away from the vibrancy of Duval Street. This three-bedroom villa, suitable for up to six guests, provides a secluded retreat with a private pool amidst the bustling atmosphere of Key West.

Here’s what you need to know, based on guest reviews:

  • Cleanliness: 5.0/5 – The villa shines with a perfect score, mirroring its impeccable upkeep.
  • Accuracy: 5.0/5 – Guests have found the listing description to be precise.
  • Communication: 5.0/5 – The host’s responsiveness and interaction with guests have been exemplary.
  • Location: 5.0/5 – Its prime location earns a top rating, appreciated for being in close proximity to Key West’s famous attractions while offering a private sanctuary.
  • Value: 4.8/5 – The villa presents great value for its offerings; guests find the price reasonable for the quality of experience provided.

Guests have shared glowing testimonials about their stays. Anthony from New York mentions the host’s swift response to replacing a showerhead, highlighting the attentiveness towards guests’ comfort. Martin praises the villa’s cleanliness and phenomenal location, complementing the management’s quick communication. Kris, with a history of seven years on Airbnb, foresees a return, enchanted by the villa’s location, pool area, and overall cleanliness. Lynn from Georgia reiterates the joy of staying at Secret Villa, and Natalie from Texas points out the quiet yet central location, ideal for three couples or families with small children. Erika from Maryland encapsulates the experience as a wonderful escape into paradise, praising the privacy and serenity the villa offers, even in the proximity of Duval Street.

These reviews collectively paint a picture of a sought-after getaway that combines the convenience of location with the luxury of privacy and comfort, making Secret Villa I a cherished destination for those venturing into Key West.

Getting The Best Deal

Was about to click “Book Now” on Airbnb for this stunning hideout, but decided to check HiChee first. Good thing I did! Saved $2,546 by booking through VRBO instead of Airbnb. More moolah for island adventures, baby!

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Stunning Beach Front Airbnb In Marathon

Oceanfront *PARADiSE* Amazing views, pool, dock

Location: Marathon, Florida

Photo Credit: Airbnb

Dreaming of a vacay where the Atlantic is your backyard? Say hello to your next insta-famous retreat in Marathon. This sleek, newly built spot doesn’t just offer views; it’s a front-row seat to the ocean’s grandeur, visible from every nook. Think luxury with a side of sea breeze, all wrapped up in a 4 bed, 4.5 bath package that’s straight up vacation goals.

Kitchen’s a showstopper, equipped for those who live to cook (and eat) in style. Dining in or out? Your call. The outdoor grill’s waiting for your culinary showdown. And for the afterparty, the living room’s got a giant TV, perfect for those lazy, do-nothing-in-particular nights.

But hey, let’s talk outside because that’s where you’ll live it up. Poolside lounging on the deck, with a saltwater pool that’s got its own sun shelf? Yes, please. And when the ocean calls, your boat’s right there, with 55 feet of dock waiting.

If you’re driving in with your crew, there’s room for four vehicles plus the boat trailer. And don’t sweat the small stuff; from check-in to check-out, there’s someone on call, because this getaway is all about the easy life.

Nearby, you’ve got the Aquarium Encounters for some up-close marine life and the Turtle Hospital for a dose of cute. Plus, with endless ocean at your doorstep, every day’s an invitation to dive, fish, or simply bask in the Keys’ glory.

From the owner:

Welcome to your gorgeous newly built vacation home curated with your utmost enjoyment in mind. Stunning open water views of the Atlantic Ocean, FROM EVERY ROOM. 55 feet of dock space to dock boats up to 35 feet. Our new construction 4 bed/4.5 bath home features stunning ocean views from every room, a private pool, outdoor seating with outdoor grill in your private backyard paradise, 2 upper level balconies, and an expansive pool deck. Welcome to paradise!

VACA-22-341

Our beautiful home is the perfect destination for your trip to the Florida Keys. This home is newly constructed with all of your vacation needs in mind. If you’re looking for the best ocean views on the island, boater friendly, fishing friendly, and spacious luxury – welcome home! Saltwater pool in your private backyard oasis will be sure to provide endless relaxation. Outdoor dining space covered area with outdoor grill for your use. AND it gets better, the entire interior is thoughtfully designed to make sure your stay is comfortable and stylish. Floor to ceiling windows showcase the exceptional Atlantic ocean views from each room of the house. This home is the ideal place to create fun memories and an unforgettable vacation.

1st Level

On the first level of the home is a bright and open floor plan with upscale kitchen, fully equipped and stocked with all appliances and dishware needed to cook up a five star meal, spacious dining area with seating for eight guests plus four more seats on the kitchen island, and the comfortable living area centered around large, flat screen TV. Floor to ceiling windows highlight the views of the Atlantic Ocean and open up to the large first level balcony furnished with Adirondack chairs, perfect for enjoying your morning cup of coffee before starting your day. Stairs from this balcony lead down to the pool area. The first level of the home also features a Suite with a King sized bed, en-suite bathroom, and walk-in shower. More floor to ceiling glass doors lead to the balcony and are covered by blackout window treatments for those that wish to sleep in. A separate half bathroom is located across the hall for your convenience when in common areas.

2nd Level

Upstairs is the remaining bedrooms and a full sized washer and dryer. The Primary suite features a King sized bed with an en-suite bathroom and large soaking tub while the third and fourth bedrooms are furnished with another King sized bed and a Queen sized bed with a pullout twin trundle bed respectively. These additional bedrooms also feature en-suite bathrooms with walk-in showers. All of the upstairs bedrooms look out over the open ocean with access to the upper level balcony and floor to ceiling glass doors. All bedrooms are equipped with blackout shade window treatments and flat screen Smart TVs.

Beyond the amazing views, another highlight of this home is the brand new swimming pool with a built in sun-shelf. Beautifully designed and located to catch as much of the Florida Keys sunshine as possible; you will have a hard time leaving! The spacious pool deck is furnished with multiple poolside loungers and more Adirondack chairs situated on the sandy beach area overlooking the pristine ocean water. Cook up your catch of the day in the covered, outdoor kitchen featuring a built-in gas grill and ample counter space.

Guest Reviews For This Rental

The Airbnb listing in Marathon, Florida, boasts an impeccable overall rating of 5.0 stars from guests, reflecting its exceptional qualities across various categories.

Here’s what you need to know, based on guest reviews:

  • Cleanliness: 4.9/5 – Achieving a near perfect score, the property is praised for its tidiness. Guests highlighted the cleanliness as a key component of their comfortable stay, indicating meticulous upkeep and attention to detail.
  • Accuracy: 5.0/5 – The accuracy of the listing’s description is top-notch. Reviewers consistently noted that the amenities, views, and overall experience matched or exceeded their expectations based on the listing details.
  • Communication: 5.0/5 – Communication with the host, Amanda, is highlighted as proactive and highly responsive. Guests appreciated her eagerness to ensure a smooth check-in process and her availability to address any queries promptly.
  • Location: 4.9/5 – The property’s location is celebrated for its stunning ocean views and accessibility to local attractions. It serves as an ideal base for exploring Marathon’s beauty and engaging in activities such as fishing, snorkeling, and visiting nearby conservation centers.
  • Value: 5.0/5 – The value for money is perceived as excellent. Guests felt that the luxurious amenities, including a private pool, spacious accommodations, and exclusive oceanfront access, offered significant worth for the price paid.

In various testimonials, guests shared personal experiences of their stays, painting a picture of a paradisiacal retreat perfect for family getaways and group vacations. They lauded the property for its beautiful design, the convenience of each bedroom having its own bathroom, and the seamless indoor-outdoor living spaces. Notably, the outdoor amenities like the pool and grill area received special mentions for enhancing their stays. The host’s thoughtfulness in equipping the house to cater comfortably to large groups was frequently acknowledged, with many expressing a desire to return.

Getting The Best Deal

Ready for a taste of luxury in Marathon? This vacation rental on Airbnb promises just that – stunning ocean views, top-notch amenities, and total relaxation. But before you seal the deal, let HiChee do its thing. Copy the property code, paste it on HiChee, and watch the magic unfold. You might just find the same slice of paradise on VRBO for $903 less. Don’t miss out on the chance to save while living the high life.

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The Best Key West Airbnb With Dock And Jacuzzi

Villa Murano

Location: Marathon, Florida

Photo Credit: Airbnb

Entire home/apt

14 Guests

6 Bedrooms

5.5 Bathrooms

Ditch the basic and level up your vacay vibes in Key West, where this Airbnb spot is all about that luxe life. Think sleek, think chic, and right where the action is—yet with all the chill you need to hit the reset button. This spot is a dream for the squad or fam, comfortably hosting up to 14 peeps across four swanky bedrooms.
Inside is an all open-concept coolness. Whip up breakfast in a kitchen that’s got more gadgets than a tech store, or lounge in living spaces where the sun kisses your skin through panoramic windows. It’s like living in a postcard, no filter needed.

But let’s get real—the outdoor scene steals the show. Private pool? Check. Sunshine on tap? Double check. This is where you’ll live your best life, whether you’re sipping something cold by the water or grilling up the day’s catch.

Just a beat from Duval Street, you’re never far from Key West’s heart. Foodies, nightlife aficionados, and culture vultures will find their bliss here. And when you’re ready to ghost the crowd, your private retreat has all the zen you need.

From the owner:

Villa Murano for 14 plus guests, for families, for gatherings, for corporate retreats for celebrations, for a phenomenal stay.

Villa Murano is designed for entertaining and for island relaxation; an all-in-one oasis. It boasts a saltwater infinity pool, an expansive rooftop patio, 75’ fishing and boating dock, a jacuzzi, high end amenities, wide smooth floors of white marble tile, top-of-the-line accommodations; and all situated beautifully between a waterway and golf course.

4 Master suites: Capri, Venezia, Toscana and Verona.

Each with a bedroom that includes king-sized bed, a queen-sized Murphy bed for extra guests, walk-in closet, a private bath with luxury amenities like Tommy Bahama soap shampoo and conditioner and hair dryer, a large sitting area, couch, coffee maker and mini bar, desk area and TV with Bose surround sound and AppleTv.

2 additional bedrooms with queen-sized beds which share a bathroom.

Villa Murano has outdoor parking for up to 5 vehicles.

The on site concierge will give you a quick tour of the property.

Villa Murano is located directly across from the Florida Keys Country Club, a 9-hole golf course. Dockside Boot Key Harbor, where guests can enjoy a drink and/or meal with a sunset view and live music, is within walking distance. Publix, Winn Dixie and Walgreens are all a few minutes drive from the property. Sombrero Beach, one of the nicest beaches in the Keys, is approximately 2.5 miles away.

Villa Murano has outdoor parking for up to 5 vehicles as well as additional space for up to 3 boat trailers. Guests are welcome to use the Villa’s 6 bicycles while staying at the property. A golf cart can be made available with arrangement prior to arrival.

Arrangements can be made for additional services, such as boat charters, a private chef, Family Photographer and a Golf cart, upon request for an additional fee.

Guest Reviews For This Rental

Guest reviews for the Luxury Villa in Marathon, Florida, highlight an overwhelmingly positive experience, underscored by a perfect overall rating of 5.0 stars. This villa, cherished for its lavish amenities and beautiful setting, stands out as a guest favorite on Airbnb.

Here’s what you need to know, based on guest reviews:

  • Cleanliness: 4.9/5 – The meticulous attention to cleanliness is frequently mentioned, suggesting that the property is well-maintained and kept in pristine condition.
  • Accuracy: 5.0/5 – Reviews indicate that the property’s online description and images accurately reflect the reality, leaving guests satisfied with their expectations being met upon arrival.
  • Communication: 5.0/5 – communication with the host is highlighted as exceptional. Guests appreciate the prompt and helpful responses to their inquiries and needs.
  • Location: 5.0/5 – the villa’s location is praised for its convenience and attractiveness. Positioned near local amenities and attractions, the property offers guests an ideal base to explore the surrounding area.
  • Value: 4.9/5 – The value for the experience provided at the villa is rated almost perfect. Guests feel that the cost is justified given the villa’s extensive amenities, luxurious accommodations, and overall quality of their stay.

Guest feedback consistently praises the villa for exceeding expectations. Key highlights include the property’s luxurious facilities such as the saltwater infinity pool, jacuzzi, and expansive outdoor areas. The villa’s design caters to both relaxation and entertainment, making it a perfect choice for families, work retreats, and group gatherings. The host, James, and his team receive special commendation for their hospitality, responsiveness, and efforts to ensure a memorable stay for all guests.

Getting The Best Deal

Sleek, chic Key West vibes with a side of sunshine. This Airbnb gem is where it’s at for your squad or fam vacay. And guess what? HiChee just made it even better by uncovering a $1,902 saving on VRBO. Same spot, same dates, more cash in your pocket. Win-win!

Modern Key West Airbnb Jewel

Anglers Terrace

Location: Marathon, Florida

Photo Credit: VRBO

Entire home/apt

10 Guests

4 Bedrooms

3 Bathrooms

Dubbed by Condé Nast Traveler as one of Florida’s Airbnb jewels, this newly built tropical oasis in Key West is where luxury meets serenity, wrapped in the laid-back vibe of the Conch Republic. It’s a two-story paradise, meticulously designed to offer an unparalleled vacation experience, perfect for those seeking an exclusive retreat amidst the vibrancy of Key West.

From the moment you step inside, the villa’s Zen-inspired decor and open, airy layout invite relaxation and togetherness. The living spaces, adorned with carefully selected furnishings, flow seamlessly into an open kitchen. Here, quartz countertops, stainless steel appliances, and an inviting eat-in island await those culinary adventures, blending functionality with sleek design.

But the true essence of Key West living extends beyond the indoor spaces. The outdoor patio deck and the rooftop terrace are where this property truly shines, offering private, quiet settings against a backdrop of panoramic ocean views. Whether it’s a morning yoga session as the sun rises or an evening cocktail under the stars, these spaces are your personal canvas for creating unforgettable moments.

And because no island oasis would be complete without a pool, this property features a pristine swimming area that can be heated for an additional fee, ensuring comfort regardless of the season. It’s a perfect spot for lazy afternoons or for kids to splash around under the sun.

From the owner:

As published in Condé Nast Traveler, this is one of the best stays in Florida.
https://www.cntraveler.com/gallery/best-airbnbs-in-florida

This Newly Built two story home was designed as a Tropical Oasis where you can reach relaxation with all amenities necessary meeting functionality and practicality.

An open, very light & spacious floor plan, carefully appointed furnishing, amenities, and a great location provide the perfect surroundings. Decorated with a Zen sensibility, Its outdoor Patio deck and Rooftop Terrace extend the living space into a private ocean setting inclusive of panoramic views.
Angler’s Terrace has a total of 4 Bedrooms, 3 Full Baths, supplied with hotel quality pillow top mattresses and Lush cotton sheets. Upstairs, you will find a King bed with its own full Bath, a Queen in 2nd Guest Room, and a full over full bunk bed In 3 Guest Room (sharing a bath). Downstairs, you will find a Queen in the 4th Guest Room with its own private bath. (Queen sofa bed also available)

The Living area is conveniently equipped with everything necessary to prepare your fresh catch of the day. The state of the art kitchen offers an open kitchen concept with quartz countertops, stainless steel appliances, and an eat in kitchen island, comfortably seats 10. Large sliding glass doors offer breathtaking water views.

There is a front load washer and dryer for your convenience. With high speed WIFI all around the house.
Angler’s Terrace has all your fishing necessities covered. It is perfectly located on ocean side minutes away from the reef, yet close enough to the seven-mile bridge for access to gulf side fishing. There is a fillet table for cleaning, freezer for bait, water, electricity and an outdoor shower. There two grills also provided. The total dock is 60 ft. 28ft can be used for your vessel (if we need a larger space for your boat please let us know). Canal is 35 feet deep and we have ample parking for 3 cars and your trailer on the side of the house

Not a fisherman…. Relax in our lounge chairs by the gunite pool while listening to water from the deckjets of the pool (heating optional), or take a five-minute drive to Sombrero Beach, or a 10-minute drive to Bahia Honda Beach to get some sand in your toes.

Angler’s Terrace is located just south of mile Marker 49 by Tranquility Bay Resort. Only one hour to Key West (depending on traffic) and two hours to Miami. Direct access to ocean with 60ft of total dock of which 30ft can be used for your boat. (Unless you arrange for full space). Excellent fishing, diving, snorkeling, and sandbars are only minutes away.

Guest Reviews For This Rental

Anglers Terrace, showcased in Condé Nast Traveler as a premier Airbnb option in Florida, garners high praise across all guest review categories. This meticulously crafted tropical oasis boasts an impressive overall rating of 4.98 out of 5 stars, reflecting the satisfaction of its guests.

Here’s what you need to know, based on guest reviews:

  • Cleanliness: 5.0/5 – Guests consistently commend the property’s pristine condition, highlighting the host’s attention to maintaining a spotless environment.
  • Accuracy: 5.0/5 – Visitors appreciate the truthful representation of the property in its listing, ensuring no unpleasant surprises upon arrival.
  • Communication: 5.0/5 – The host, Andy, is recognized for exemplary communication. His prompt and helpful responses are frequently noted, contributing significantly to a smooth and enjoyable guest experience.
  • Location: 5.0/5 – This score emphasizes the property’s desirable setting. The strategic location offers easy access to local attractions, enhancing the overall convenience and appeal for visitors.
  • Value: 5.0/5 Echoing the trend, the value provided by Anglers Terrace receives a top rating. Guests express that the experience offered is well worth the investment, citing the combination of amenities, location, and service excellence as key factors.

The guest reviews vividly illustrate a consistent pattern of excellence across all evaluated aspects. From families to groups on various trip types, the feedback is overwhelmingly positive. Guests highlight the spaciousness and the beauty of the home, the enjoyable pool area, and the convenient location close to beaches and dining options in Marathon. The property’s host, Andy, is repeatedly praised for his responsiveness and hospitality, further accentuating the stellar guest experience.

Getting The Best Deal

Picture-perfect views, open spaces, and an island vibe – this Key West villa Airbnb has it all. And guess what? You can save big by using HiChee! I snagged an extra $1,377 off on VRBO for the same dates and guests. Don’t miss out on maximizing your vacation budget!

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Bonus Property

Best Key West Airbnb With Airbnb Old School Charm

Takeover at the Grand Maloney by Brightwild

Location: Key West, Florida

Photo Credit: Airbnb

Entire Home

16 Guests

6 Bedrooms

6.5 Bathrooms

Last on our list is this chic holiday home where the old school charm of Caroline Street gets a fresh, luxe makeover.

Six bedrooms mean space isn’t just a luxury—it’s a given. King beds dominate, but there’s also that queen bunk setup for when the squad’s all here. And because privacy is key, each room rocks its own bathroom. It’s like they know sharing’s not always caring.

Chill in the lobby or lounge, then dip into the heated pool on the private patio. Craving a caffeine fix or a midnight snack? The kitchen’s got you, with espresso on tap and fridge space to spare.

Forget the check-in hassle; here, it’s all digital, all smooth. And once you’re settled, the best of Key West waits just steps away. Duval Street’s legendary scene? A short walk. The best key lime pie you’ll ever taste? Practically on your doorstep.

Riding solo or with the crew, it doesn’t matter. The Grand Maloney’s got the space, the style, and the setup for an epic Key West adventure. And with no parking drama (thanks to nearby lots), your stay is all about the good times, zero stress.

From the owner:

The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red brick, historical home on Caroline Street has been lovingly restored with a brand-new heated dipping pool on its private patio. With undeniable character, the two-story house stands out from the traditional cottages of Key West in the same way the Grand Maloney stands out from other boutique hotels in the area.

This modern hotel boasts creative, interior design concepts and takes luxury living to a whole new level. Featuring a lobby, lounge, wrap-around balcony, private pool, patio and lounge chairs, the red brick home provides ample common space. The kitchen area encompasses two large refrigerator drawers, an espresso maker, sink and select glassware. Allow our team of guest experience managers to become your personal shoppers, coordinators and event planners!

The entire house features 6 bedrooms and 6.5 bathrooms for up to 16 guests. Sleeping arrangements include 5 king beds and 2 queen beds and a queen size pullout couch. Each bedroom also features an attached full bathroom for privacy and space:

Room 1: Queen over Queen Bunk Beds

Room 2: King bed with Queen pullout couch

Room 3: King bed in attached Carriage House

Room 4: King bed

Room 5: King bed

Room 6: King bed

Your next luxury getaway awaits!

Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.

Placed perfectly between downtown and the Historic Seaport, enjoy walkable attractions like Fury Water Adventures for a day at sea, the Mel Fisher Maritime Museum for some Key West history and the famous Mallory Square for a Sunset Celebration.

Half a block from Duval Street, the Grand Maloney Hotel is steps away from Key West’s most famous bars and kitchens. Food is at your finger tips with local’s favorite restaurants, such as First Flight, Bagatelle and Two Friend’s Patio, less than a 5-minute walk from your front door. Got a sweet tooth? Keep an eye out for Kermit’s Key Lime Pie Shoppe known for the best key lime pie in Key West. Or, grab some homemade fudge and candy from River Street Sweets.

Forgot something or need a quick fix? Shorty’s Market has your last minute necessities for your weekend getaway. Just 2 blocks away, you will also find Fausto’s Food Market with locally sourced groceries.

There are a variety of great ways to explore Key West whether it be by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or foot. Being in the heart of downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!

Guest Reviews For This Rental

The Grand Maloney Hotel in Key West, Florida, boasts a perfect 5.0 overall rating from guests, reflecting its excellence in every aspect. This property, hosted by Brightwild, has received praise for its cleanliness, accuracy, communication, location, and value, making it one of the most loved homes on Airbnb. Here’s a detailed breakdown:

  • Cleanliness: 5.0/5 – Guests consistently awarded a perfect rating, highlighting the property’s immaculate condition.
  • Accuracy: 5.0/5 – Also perfect-rated, indicating that the property matches its online description and photos accurately.
  • Communication: 5.0/5 – Brightwild’s communication is top-notch, showing that they are responsive and attentive to guest needs.
  • Location: 5.0/5 – Guests love the property’s location—ideally situated for exploring Key West’s attractions.
  • Value: 4.8/5 – Close to perfect, suggesting that staying here is considered worth the expense.

Reviews reveal guests’ high satisfaction, with personal testimonies praising the property’s exceptional standards, from its stylish decoration and prime location to the seamless check-in process and the host’s accommodating nature. Whether for group trips or family stays with children, the Grand Maloney Hotel emerges as a standout choice for those seeking a luxurious, hassle-free experience in Key West.

Getting The Best Deal

Planning your Key West getaway? The Grand Maloney is calling your name. But before you book, here’s a tip: use HiChee. Just copied the code from Airbnb, pasted it in, and voila! Found the same spot on Booking.com and VRBO for $1,326 less. Who doesn’t love extra vacation cash?

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Price Check These Properties?

We’ve created an easy-to-use collection (a HiChee trip list) that you can use to check availability and compare prices for all of the above properties.

Just click on the image below, select your dates and the number of guests, and HiChee will instantly show you which properties are available and how much each one costs for those dates.

You can even choose to receive price and availability alerts straight to your inbox.
By clicking on the three dots icon, you can share your trip list with friends or family

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