Airbnb Anna Maria Island: The Ultimate Guide to Beachside Escapes

Airbnb Anna Maria Island: For those plotting a getaway to Anna Maria Island—often cheekily referred to as Anna Maria Cay—anticipate an experience far from the ordinary. This Gulf Coast gem serves a unique blend of chill vibes and scenic splendor, making it a haven for short-term rental seekers and Airbnb enthusiasts.

Here, the lodgings come with a side of lifestyle envy. Guests get more than a key; they snag a slice of island life. Whether it’s a condo that’s steps away from the surf or a villa where the pool is lit 24/7, these places are about leveling up your vacation mode. And with amenities that span from chef-grade kitchens (because some nights, it’s all about that home-cooked goodness) to outdoor lounges perfect for ending the day with a sunset toast, it’s clear: Anna Maria doesn’t do average.

And speaking of sunsets, they’re practically a religious experience here, best enjoyed from the comfort of a hammock or a rooftop deck, cold one in hand.

But hold on, Anna Maria isn’t just about gorgeous Airbnbs. The island’s food scene is a brimming cauldron of culinary delights, ranging from casual dockside dining to upscale restaurants where the views rival the masterfully plated dishes–trust us, it’s gonna be hard to decide which one to take a picture of first. And with the island’s eco-friendly trolley service, zipping from beach lounging to gourmet feasting is a no-car-needed affair.

So, if you’re ready to plunge into the island’s breezy charm, vibrant sunsets, and cozy corners, ‘ring ring’—pick up your phone; Anna Maria Island is calling!

An introduction to Anna Maria Island, Florida

If you’re visiting the island for the first time, this video will give you a great idea of what to expect in the way of beaches, attractions, restaurants, and more.

– What is Anna Maria Island known for? (1:03) – Anna Maria (2:30) – Anna Maria Island City Pier (3:00) – Rod & Reel Pier (3:50) – Bean Point (4:17) – Galati Yacht Broker (4:37) – Holmes Beach (5:58) – School Key (6:50) – Key Royal Club (6:57) – Sandbar Restaurant (7:20) – Beach Bistro (8:04) – Bradenton Beach (8:13) – Historic Bridge Street (8:27) – Anna Maria Oyster Bar (9:05) – Coquina Beach (9:45)

Our selection of rental properties

Click any of the images below to view the property directly

Airbnb Bradenton Beach, Florida

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

Location: Bradenton Beach, Florida

Ready to level up your vacay vibes on Anna Maria Island? Say hello to your dream escape: a chill, beachfront apartment that’s all about those Gulf of Mexico views. This isn’t just any stay; it’s your front-row ticket to paradise, complete with dolphin sightings and sunset stories that’ll have your Insta fam hitting ‘like’ faster than you can say “beach please.”

Nestled right on those sugary sands, this one-bedroom haven is where comfort meets cool. Kick back in a space that boasts a king-size bed you won’t want to leave, a cozy sofa bed for the extra tagalongs, and central AC to keep you cool after a day under the sun. Binge-watch to your heart’s content with Ultra HD magic in the living room and another 48′ screen in the bedroom because, let’s face it, vacation is for guilty pleasure TV marathons too.

But wait, there’s more! A kitchen so stocked, you might actually want to cook. Beach gear? Covered, with chairs and an umbrella. Plus, WiFi and charging spots for endless scrolling and bragging rights.

The building itself is pretty rad, offering BBQs for those sunset grilling sessions, a hot tub to soak away the real world, and even coin washers and dryers because sand, although cool, doesn’t belong in your suitcase.

From the owner:

An unforgettable experience awaits you at this getaway apartment right on the white sand beaches of Anna Maria Island. Wake up every morning to the best views of the turquoise waves of the Gulf of Mexico and spend your days enjoying the warm waters, filling your Instagram feed with dolphin pictures and dramatic sunsets.

Guest reviews for this Airbnb Anna Maria Island rental

The condominium titled “★Right on the beach ★ Relax and Enjoy ♥ Sunsets!” located in Bradenton Beach, Florida, has received overwhelming praise from its guests, holding an exceptional overall score of 4.99 from 90 reviews.

Here’s a breakdown of how guests rated their experience:

• Cleanliness: 5.0 stars, indicating a spotless and well-maintained environment.
• Accuracy: 5.0 stars, showing that guests found the property exactly as advertised.
• Communication: 5.0 stars, highlighting Martha’s effective and prompt communication.
• Location: 5.0 stars, underscoring the prime beachfront location and easy access to local attractions.
• Value: 4.9 stars, suggesting guests found the stay to be worth every penny.

Guests have consistently highlighted the property’s incredible location, allowing for direct beach access and stunning sunset views. The condo is praised for its cleanliness, stylish decor, and well-stocked amenities, including beach chairs, umbrellas, and a fully equipped kitchen.

The private beach access and proximity to local dining and shopping add to the allure of staying here. Martha, the host, receives special commendation for her attentiveness, responsiveness, and the personal touch she adds to ensure a memorable stay. This property is a favorite for those seeking a peaceful beach getaway with all the comforts of home, making it one of the most beloved homes on Airbnb.

Getting The Best Deal

Waking up to the sound of crashing waves at a beachfront apartment on Airbnb. Sounds idyllic, right? Well, hold your horses! By using HiChee, I found the exact same oasis on VRBO for $67 less. It’s as simple as copying the Airbnb property url and pasting it into HiChee to unlock these secret savings. Your wallet will thank you later!

Anna Maria Island Airbnb With Hot Tub

Tripletail

Location: Anna Maria, Florida

Elevate your getaway game at this Anna Maria Island retreat where the ordinary is left at the doorstep. This home throws the rulebook out the window, offering a quartet of king-sized sanctuaries that redefine relaxation with their en-suite havens. The living quarters? A masterclass in blending culinary arts with lounging luxuries, set in an architecturally savvy layout that promotes both unity and solitude.

The living area, a masterpiece of design, blurs the lines between inside and outside life. It’s a culinary dream space that opens into communal zones designed for connection and quiet moments alike. Step into the outdoor oasis where a heated pool and hot tub wait to soothe your soul, framed by vistas only the Gulf can offer.

Beyond the threshold, the Gulf of Mexico extends an exclusive invitation to its waters. Enjoy some splish-splashing fun where every day feels like a tropical vacation.

Mobility on the island becomes an adventure with a golf cart at your disposal, ensuring that every local gem, from Pine Avenue’s boutiques to gastronomic delights, is but a joyful ride away.

From the owner:

Private Beachfront Home – one block from Pine Avenue and the City Pier. Watch dolphins and manatees swim by from your back deck. Bike or take the golf cart (included) to explore the island and boutique shops and restaurants. Ground floor has a beachfront king bedroom with en-suite bathroom, second king bedroom and bathroom, open floor plan kitchen , dining and family room. Upstairs are two more King bedrooms and bathrooms as well as a sitting area.

Heated pool and hot tub

Beachfront! Walk out your back door to your own beach and gently sloping waters. Watch dolphins and Manatees swim by.

Lockbox on the home. Code Provided after all documentation is complete.

We are available on island if you need anything. Call or text 813*748*8215

Anna Maria Island, paradise….

Laid-back and natural, Anna Maria Island is a mere 20 minutes from Bradenton, 45 min from Tampa or Sarasota.

A seven-mile strip of beautiful sugar-white-sand beaches lines the barrier island of Anna Maria Island between the turquoise Gulf of Mexico and peninsular Florida.

Strict regulations govern the type of buildings and businesses allowed on Anna Maria Island, giving it an old-time feel. Excellent dining – seafood, of course! – is very much encouraged. Come visit – you well might feel as though you have journeyed to an elegant past.

We supply all you need… golf cart and bikes.

For a trip to Longboat Key, take advantage of the free Trolley

2022 Heated Pool and fenced yard with turf. Note: The driveway is still under repair/replacement.

Guest reviews about this vacation rental

The “Tripletail” home, located in Anna Maria, Florida, has garnered high praise from guests, boasting an impressive overall rating of 4.94 stars from 53 reviews. This private beachfront property is celebrated for its stunning location, just a block away from Pine Avenue and the City Pier, providing breathtaking views of dolphins and manatees from the back deck. The inclusion of a golf cart for exploring the island’s boutique shops and restaurants adds a unique and appreciated touch to the stay.

Here’s a breakdown of guest ratings across key areas:

• Cleanliness: 5.0 stars, indicating a spotless and well-maintained home.
• Accuracy: 5.0 stars, showing the property exactly as advertised.
• Communication: 5.0 stars, highlighting the host’s effective and prompt communication.
• Location: 5.0 stars, underscoring the property’s prime beachfront location and easy access to local attractions.
• Value: 4.9 stars, suggesting guests found the stay to be worth the price.

Guests consistently commend the home for its beautiful interior design, family-friendly amenities, and the incredible convenience of having a private beach and gently sloping waters right at their doorstep.

The addition of a heated pool and hot tub in 2022 has been a hit among guests, offering an extra layer of luxury and relaxation. The host, Serendipity, is lauded for their hospitality, ensuring a memorable and enjoyable stay for all visitors.

The “Tripletail” stands out as a favorite for families and groups looking for an exquisite beachfront experience in Anna Maria.

Getting The Best Deal

Found this paradise on VRBO but decided to do a quick HiChee search. Lo and behold, HiChee revealed the exact same place on Airbnb for $322 less! Can’t thank HiChee enough for the extra cash in my pocket.

Bean Point Airbnb Anna Maria Island

Serendipity – Beach Front 4/3

Location: Anna Maria, Florida

Take a deep plunge into the heart of Anna Maria Island where a four-bedroom oasis waits to flip the script on your usual beach escape. This place isn’t just about staying; it’s about experiencing. With Bean Point’s sands whispering tales of sunsets and sea, adventure and chill blend like the colors of the evening sky.

Elevate your vacation literally and figuratively with an elevator accessing all floors, making every corner of this retreat effortlessly reachable. The layout? Think king-sized dreams in three bedrooms, with the fourth a bunk bed bonanza for the squad or fam. It’s all about squad goals, with spaces that invite stories and laughter. The master suite? That’s your recharge zone, complete with a bathroom that’s all spa vibes.

Gear up for island exploration with bikes and a golf cart on the house, paddling adventures with SUPs and a kayak, and yes, an elevator to lift you through the stories of this retreat. While the pool’s on the horizon, the ocean’s timeless embrace is your playground for now.

From the owner:

Beach front Bliss… Enjoy Swimming or relaxing in this 4 bedroom home on the North End of Anna Maria Island. Captivating Sunsets from your deck or steps away at the famous Bean Point. Elevator to all floors

4 Adult Bikes, golf cart, 2 SUP’s and a tandem Kayak are all included

Elevator to all floors

Guest reviews about this beach rental

The “Serendipity – Beach Front 4/3” home in Anna Maria, Florida, has an excellent overall score of 4.89 stars from 19 reviews. This beachfront property is a hit among guests for its stunning views, spacious accommodations, and numerous amenities.

Here’s a breakdown of how guests rated their experience across key areas:

• Cleanliness: 5.0 stars, indicating a spotless and well-maintained environment.
• Accuracy: 4.7 stars, showing minor discrepancies between the listing and the actual experience but overall satisfaction.
• Communication: 5.0 stars, highlighting the host’s effective and prompt communication.
• Location: 4.9 stars, underscoring the prime beachfront location and the beauty of its surroundings.
• Value: 4.7 stars, suggesting guests felt the experience was worth the price.

Guests consistently praise the property’s incredible location, offering direct beach access and breathtaking views of dolphins, manatees, and sea birds from the deck. Including a golf cart, SUPs, and a tandem kayak for exploring Anna Maria Island and its waters has been especially appreciated. Although the absence of a pool was noted, the promise of a new one being in the works has guests excited for future stays.

The hosts, known for their great communication and helpfulness, have made “Serendipity” a favorite among families, groups, and those seeking a relaxing beachfront retreat with all the comforts of home and more.

Getting The Best Deal

Beach lovers, listen up! Found this dreamy retreat on VRBO, but hold onto your sunhats because HiChee showed me I could save $460 by booking it on Airbnb instead. Same property, same beachy vibes, just more savings in my pocket!

Anna Maria Island Airbnb With Private Pool

True beachfront home

Location: Holmes Beach, Florida

“Waves Edge North,” where Anna Maria Island’s vibe gets real. This isn’t your grandma’s beach house; it’s a slice of coastal cool, redefined. It’s where old Florida’s laid-back essence marries the now, all set against a backdrop of jaw-dropping beachscapes that’ll have your Insta followers green with envy.

Here’s the deal: three bedrooms, two baths, and space that screams beach chic. You’re looking at beach access so direct, your mornings start with sand between your toes. The place is a hop from the buzz of shops and bites, plus the free Island Trolley’s practically your personal chauffeur.

Inside, it’s all about spaces that flow like a chill playlist. Vaulted ceilings, windows wide open to the Gulf’s glory, and a living area that’s all about vibing out, complete with tech goodies for nights in. The deck? It’s your open-air lounge, grill included, because why not dine with a view?
Sleep setup’s on point: a king suite for the dreamers, two queens for the resters, and a loft that’s every teen’s hideout dream. Then there’s the pool scene—think sun-soaked days, heated for your comfort from December to April, challenging the ocean for your affections.

From the owner:

This lovely 3 bedroom 2 bathroom home is situated on one of the most beautiful beaches imaginable; nestled among the sea oats leading out onto the white sand beaches and crystal clear waters this area is so famous for.

As you cross the bridges and gaze at the glittering turquoise water fringed by swaying palms you will quickly realize that you have stepped back into old Florida – a slice of paradise that transports you back to a time when the pace of life was slower, gentler and more carefree.

Just a stone’s throw from shops restaurants and shopping and very close to stops for the free Island Trolley which runs the length of the island seven days a week from 6am to 10pm, this may be the best location on the island!

Waves Edge North with its vaulted ceilings and a wall of windows brings the outside in and gives you sweeping views of the Gulf of Mexico. Enjoy the cozy comfortable living area with flat screen Smart TV, Cable, DVR and DVD. Meals are easy to prepare in the fully equipped open plan kitchen or you can step out into the fresh ocean breezes on the spacious deck where you can cook out on the gas grill while enjoying the beautiful views.

Waves Edge will comfortably sleep 6 people. The master bedroom has a king bed, Smart TV and en suite bathroom with walk in shower. The two guest bedrooms have queen beds, Smart TV’s and share a bathroom with a combination bathtub/shower. There is a really cool sleeping loft with two twin beds – ideal for older children or teenagers.

From the outside deck steps lead down to a beautiful heated swimming pool with plenty of loungers for you to relax. To swim in the pool or walk across the sugar sand to the ocean – that may just be the most difficult decision you have to make each day!

Guest reviews about this beachfront Airbnb on AMI

The “True beach front home – 3 beds/2 bath, heated pool” located in Holmes Beach, Florida, has earned rave reviews from guests, achieving an impressive overall rating of 4.95 stars from 37 reviews. This beachfront property is a hit for its stunning location, amenities, and the serene experience it offers.

Here’s how guests rated their stay across various aspects:

• Cleanliness: 5.0 stars, indicating that guests found the home to be exceptionally clean and well-maintained.
• Accuracy: 4.7 stars, suggesting that the property mostly lived up to guests’ expectations based on the listing, with minor discrepancies.
• Communication: 5.0 stars, highlighting the host’s prompt and clear communication.
• Location: 4.9 stars, underscoring the prime beachfront position and accessibility to local attractions.
• Value: 4.7 stars, indicating guests felt the experience was worth the price.

Guests have consistently praised the property for its breathtaking views, direct beach access, and additional amenities like the heated swimming pool and the inclusion of bikes, a golf cart, SUPs, and a tandem kayak. The home’s interior is lauded for its comfortable and spacious layout, which is suitable for families or groups.

The host, Nicky, receives special commendation for being accommodating and ensuring a smooth stay for guests. This property stands out for those seeking a tranquil beach getaway with all the comforts and conveniences of home, plus the added luxury of being steps away from the white sandy beaches.

Getting The Best Deal

Beach lovers unite! Found this gem, “Waves Edge North,” on VRBO, ready to book for a coastal getaway. But hold the seashells! HiChee revealed that Airbnb has it at a steal, saving us $530 for the exact same beachfront bliss. Time to catch those waves and those savings!

AMI Airbnb At Bimini Bay

Bimini Bay Vue

Location: Anna Maria, Florida

Next on our list is this gorgeous property in Bimini Bay that’s fresh from a recent glow-up. This four-bed, four-bath haven rocks a layout that’s all about blending spaces—where bedrooms serve as private retreats, each paired with bathrooms that dial up the luxe. Picture this: waking up, rolling out of bed, and stepping straight into a spa-like shower. The heart of the home beats with a coastal palette, inviting you to kick back in an open-plan living area that’s prime for everything from brunch spreads to late-night convos.

Culinary geniuses, get stoked. The kitchen’s kitted out with top-tier Jenn Air appliances (swanky, we know!), set against a backdrop of sleek glass tiles. And those meals? Take them outside. Your deck overlooks Bimini Bay, making every bite a moment and every gathering Insta-gold.

This spot’s location is on point, a few blocks from the buzz of Pine Ave and moments from the whisper-soft sands. Whether it’s your crew or just you, this home’s a leap into the laid-back luxe life, where your toughest call is beach or poolside lounging.

From the owner:

You won’t be disappointed with this new home! This 4 bedroom, 4bathroom home is located in the heart of ANNA MARIA ISLAND! When you enter the home you are greeted by beautiful coastal decor in soft hues of light blues and corals.

The open living, dining, and kitchen areas are the perfect spot to host a family meal, game night, or just relax and take a load off. The kitchen has Jenn Air appliances that are accented by a breathtaking glass backsplash and white custom cabinets!

The living room opens up to a spacious back deck seating area overlooking Bimini Bay. The pool allows for stunning views while swimming in the spacious swimming.

The entire home was professionally decorated with luxury and comfort in mind.

A dining room sits 8 comfortably, and the kitchen island seats 4. 3 Bedrooms have ensuite bathrooms. The remaining bedroom has the use of a full bathroom nearby.

The home is a few blocks walking from Anna Maria’s famous shopping district, Pine Ave. If you ever want to leave your private oasis, the home is a short five-minute walk to the white sandy beaches!

Guest reviews about this AMI vacation rental

The “4 Bed / 4 Bath with Stunning Views of Bimini Bay!” home in Anna Maria, Florida, boasts a flawless overall rating of 5.0 stars from 11 reviews. This beautifully renovated property offers breathtaking views, professional coastal decor, and a plethora of amenities that ensure a comfortable and luxurious stay for guests.

Here’s how guests rated their experience across various aspects:

• Cleanliness: 5.0 stars, indicating that the home is exceptionally clean and well-maintained.
• Accuracy: 5.0 stars, showing that the property matches or exceeds the expectations set by the listing.
• Communication: 5.0 stars, highlighting the host’s promptness and clarity in communication.
• Location: 5.0 stars, emphasizing the home’s prime location with stunning bay views and proximity to local attractions.
• Value: 5.0 stars, suggesting that guests found the experience to be well worth the price.

Reviewers have consistently praised the property for its beautiful design, high-end finishes, and comfortable accommodations. The home’s amenities, including a designer kitchen, spacious living areas, and a heated pool overlooking Bimini Bay, have been particularly appreciated. Including multiple outdoor sitting areas allows guests to enjoy the scenic views and Florida’s beautiful weather.

The host, Patrick, is commended for his hospitality and for ensuring a smooth and enjoyable stay for all guests. This property stands out for those seeking a luxurious beachfront experience with all the comforts of home, making it an ideal choice for families and groups looking for an unforgettable stay in Anna Maria Island.

Getting The Best Deal

Just came across this luxe retreat on Airbnb, perfect for a relaxing getaway. But wait, there’s more! HiChee guided me to VRBO where it’s $223 less for my selected dates and guests. Score one for smart spending!

Bradenton Beach Airbnb On Anna Maria Island

Capri Condo D

Location: Bradenton Beach, Florida

Immerse yourself in the quintessential Anna Maria Island experience with this chic, second-level condo, offering front-row seats to the Gulf’s mesmerizing blues and golden sunsets. This is your golden ticket to the laid-back rhythms and scenic beauty that Anna Maria, often dubbed “Paradise Without an Attitude,” is celebrated for.

Positioned directly on the Gulf beaches, this modern escape lets you wake up to the sound of waves and the soft embrace of sunlight. With its prime location, you’re just a leisurely stroll from the vibrant Bridge Street, where island vibes and local flavors collide in a symphony of experiences waiting to be discovered.

Effortless living defines this space, part of the owner’s Professional Linen Program, ensuring a touch of luxury in every thread count. The convenience doesn’t end there; a washer/dryer on-site means you’re always beach-ready, making it easier to embrace the spur-of-the-moment adventures that call to you.

From the owner:

This 2 bedroom, 2 bathroom condo sits directly on the beach with gorgeous views of the Gulf of Mexico. Enjoy magnificent views from the living room, kitchen, and the large open porch, perfect for watching nightly sunsets. Capri Condo D is also within walking distance to historic Bridge Street; filled with restaurants, shops, and the Bridge Street Pier!

This property also participates in our Professional Linen Program. This luxury amenity provides you with high-quality Comphy linens that are in place and ready for use upon your arrival including luxury bedding, sheets, bath towels, bathmats, washcloths, and beach towels.

Opening your door and strolling down to the beach – it doesn’t get any better than that. Sit on your porch and watch as a dolphin swims by, the seagulls land on the beach, and then, the most exquisite sunset you will ever see! When not at the beach, walk over to the many local restaurants and Island shops or catch the free Trolley to visit the northern end of Anna Maria Island. You are also close to the Cortez bridge with easy access to the mainland.

Guest reviews for this rental on AMI

The “Beachfront Condo with Views – Capri Condo D” located in Bradenton Beach, Florida, has achieved a perfect overall rating of 5.0 stars from 8 reviews. This condominium offers guests a prime beachfront location, making it an ideal choice for families and groups looking to enjoy the scenic beauty and activities of Bradenton Beach.

Here’s how guests rated their experience across various aspects:

• Cleanliness: 5.0 stars, indicating a spotless and well-maintained environment.
• Accuracy: 5.0 stars, showing that the listing accurately represents the actual experience.
• Communication: 5.0 stars, highlighting the host’s effective and prompt communication.
• Location: 5.0 stars, emphasizing the condo’s prime beachfront position and accessibility to local attractions.
• Value: 5.0 stars, suggesting guests found the experience to be well worth the price.

Reviewers have consistently praised the property for its stunning views, comfortable accommodations, and the convenience of self-check-in through a smartlock system. The host, Anna Maria Vacations, is commended for their professionalism and for providing a smooth check-in experience, as reflected in the 100% 5-star rating for check-in.

This property stands out for those seeking a serene beachfront getaway with all the comforts of home, making it one of the most beloved homes on Airbnb in Bradenton Beach.

Getting The Best Deal

Airbnb has this dreamy condo listed with panoramic Gulf views on Anna Maria Island. But don’t rush to book just yet! Popped the code into HiChee and discovered that VRBO has a sweeter deal, $269 less for the same stay dates and guests. Imagine the souvenirs you could snag with those extra savings!

Holmes Beach Anna Maria Island Airbnb

Sailfish Gulf Suites #4

Location: Holmes Beach, Florida

“Sailfish Gulf Suites” takes your beach getaway up a notch. Suite 4 is your beach-adjacent nook, serving up garden views with a side of salty air, just footsteps from the ocean’s embrace.

In this 700-square-foot slice of paradise, find a king bed that’s the stuff of dreams, plus a queen sleeper sofa for when the squad rolls deep. The bathroom? It’s got that spa-day-every-day vibe going on, ensuring you’re rejuvenated after every sandy adventure.

Outdoors, the shared patio is the ultimate hangout spot. Sizzling barbecues, cold ones in hand, under the shade of umbrellas? Where do we sign up? It’s where sunsets become your daily drama, and dolphin sightings are as regular as your morning brew. Forgot to rinse off the beach? Outdoor showers have got you covered, and there’s a laundry spot to keep those swimwear rotations fresh.

Roam a little, and Anna Maria Island unfolds like your favorite summer playlist—eclectic shops, drool-worthy eats, and that Manatee Public Beach vibe, complete with all the beach day essentials. Plus, with the free Island Trolley, you’re always a ride away from the next island gem.

From the owner:

Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation!

Sailfish Gulf Suites is comprised of 4 separate suites. Suite 4 has garden views and is just a few steps to the beach.

It features 1 bedroom with king size bed, a sleeper sofa with a queen bed, and 1 tub/shower and is approximately 700 square feet. This suite accommodates up to 4 persons.

Just steps from your suite, there is a large, shared patio area with tables, chairs, umbrellas, and a gas/charcoal grills. From there, you can enjoy wonderful island breezes, views of the dunes, and the beautiful turquoise water. Enjoy your morning coffee on the patio while the dolphins swim along the shoreline or enjoy a glass of wine while watching the most amazing sunsets. There are outdoor showers on either side of the complex for rinsing off your sandy feet and a shared laundry room on site.

Guest reviews about this Airbnb Anna Maria Island, Florida

The “Sailfish Gulf Suites #4, Garden Views, Steps from” located in Holmes Beach, Florida, boasts a perfect overall rating of 5.0 stars from 26 reviews. This charming cottage offers guests an idyllic beachfront experience with its proximity to the sand and sea, making it a highly sought-after vacation spot.

Here’s how guests rated their stay across various aspects:

• Cleanliness: 5.0 stars, indicating that the cottage is exceptionally clean and well-maintained.
• Accuracy: 5.0 stars, showing that the listing accurately represents the actual experience.
• Communication: 5.0 stars, highlighting the host’s promptness and clarity in communication.
• Location: 5.0 stars, emphasizing the property’s prime location just steps from the beach and close to local amenities.
• Value: 4.9 stars, suggesting guests found the experience to be nearly perfect in terms of value.

Reviewers consistently praise the property for its beautiful location, immaculate condition, and the convenience of self-check-in. The host, Tamie, is commended for her exceptional hospitality and responsiveness, ensuring a seamless and enjoyable stay for guests.

This property stands out for those seeking a tranquil beach getaway with all the comforts of home, making it one of the most beloved homes on Airbnb in Holmes Beach.

Getting The Best Deal

Planning your next beach escape? Look no further than “Sailfish Gulf Suites” on VRBO. But hold on a sec! Before you hit that reserve button, why not give HiChee a spin? Just by copying the code from VRBO and pasting it into HiChee, I uncovered a sweet deal on Airbnb, saving $79 for the same dates and guest count. Don’t miss out on these easy savings!

AMI Airbnb With Private Pool

The Blue Crab

Location: Anna Maria, Florida

Two blocks off the Gulf’s crystal vibes, “The Blue Crab”, this four-bed, four-and-a-half-bath crib is all about that upscale beach life. With a tropically landscaped backyard that’s more oasis than yard, you’ve got the ultimate setup for making those Insta stories pop.

It boasts of a pool with its own swim-up bar (yes, you heard that right), so you can sip something chilled from the wine fridge while gathering around the firepit or melting stress away in the hot tub. And when the island breeze calls, your covered deck is the spot to answer.

Indoors, you’re greeted with chic rustic nautical decor and an open space that’s all about vibing together. From the living room’s dry bar setup to a kitchen begging for a cook-off (Wolf oven included), it’s dialed in for chill nights and social spice.

Bedroom scenes range from a primary suite with spa feels to a loft that’s a kids’ hideaway dream, ensuring everyone’s got their chill zone. And when you’re ready to hit the sand, Holmes Beach is just a flip-flop away.

From the owner:

Welcome to The Blue Crab, a spectacular island gem with an unbelievable tropically landscaped backyard with a covered deck, a serene outdoor firepit with seating, a hot tub, and a pool with easy access to the swim-up bar with a wet bar and a wine fridge. Only two blocks from the sparkling, pristine Gulf of Mexico, this four-bedroom, four-and-a-half-bathroom home is the perfect spot for your next getaway.

Highlights

• Private pool with build-ins and spa
• Swim-up bar
• Outdoor firepit
• Balcony

The nautical farmhouse theme carries throughout the home’s open layout. There is a dry bar in the living room for refreshments, plenty of seating, and amenities designed for a large family or group of friends. The spacious functional kitchen has stainless steel appliances, including a Wolf oven and induction stovetop, a huge wine fridge, a farm sink, countertop island seating, a breakfast nook, and a dining room table.

An elegant spa ambiance fills the primary bedroom with large windows, soothing blue and brown hues, an ensuite bathroom with dual vanities, a water closet, and an enclosed walk-in shower with a soaking tub. Rest will come easily in the second bedroom, with space for beach bags, balcony access, and a modern ensuite bathroom with a walk-in shower. The third bedroom offers peace and tranquility and has hall access to the third bathroom. The younger guests will find the loft delightful, with plenty of space for recreation and an ensuite bathroom with a shower-bathtub combination. A bonus room with a TV and couch and washer and dryer are available for guest use.

Guest reviews about this Airbnb AMI vacation rental

The “Island home with swim-up bar! Best location!” in Anna Maria, Florida, garners unanimous acclaim, boasting a stellar overall rating of 5.0 stars from 5 reviews. This luxurious four-bedroom home offers guests a unique and unforgettable stay with its swim-up bar, beautifully landscaped pool area, and proximity to the beach.

Here’s a breakdown of guest ratings across key aspects:

• Cleanliness: 5.0 stars, signifying a spotless and well-maintained property.
• Accuracy: 5.0 stars, indicating that guests found the home exactly as described in the listing.
• Communication: 4.8 stars, highlighting the host’s effective communication, though slightly room for improvement was noted.
• Location: 5.0 stars, emphasizing the home’s prime location close to the beach and local amenities.
• Value: 5.0 stars, suggesting guests felt their stay offered excellent value for the price.

Reviewers consistently praise the property for its stunning design, high-end amenities, and the exceptional experience it provides, making it a favorite among families and groups seeking a premium vacation spot. The inclusion of a well-appointed kitchen, comfortable living spaces, and the enjoyable pool area, complete with a swim-up bar, were particularly appreciated by guests.

The host, Anna Maria Vacations, is commended for their professionalism and dedication to ensuring a memorable stay, with guests expressing a desire to return. This property stands out as an ideal choice for those seeking a luxurious and relaxing island getaway with all the comforts of a well-equipped and beautifully designed home.

Getting The Best Deal

Airbnb led me to “The Blue Crab,” a beach paradise. But with a quick check on HiChee, I unearthed a sweet deal on VRBO. By booking there instead, I can pocket $857 for my beachfront bliss. Who doesn’t love extra cash for cocktails by the pool?

Private Island Beachfront Home Airbnb On AMI

Tropical Private Island Retreat

Location: Longboat Key, Florida

Perched on its own 2-acre island, this bespoke sanctuary, aptly called Private Island Beachfront Home, offers boat-only access, ensuring every moment is draped in privacy and is as exclusive as it gets. With 300 feet of your own beachfront, mornings begin with salty breezes and the kind of peace you’ve only dreamt of.

The retreat unfolds with four bedrooms, each a masterclass in comfort, boasting views that turn the Gulf into your personal backdrop. Outdoor showers add a splash of adventure to your routine, blending seamlessly with the modern luxuries that dot every corner of this home.

Gear up with paddleboards, kayaks, or even a canoe, embracing “The Kitchen’s” aquatic bounty. For the landlubbers, a 200′ zip line thrills, while hammocks offer a nook for those content with a good book and a breeze.

Tech meets tranquility with high-speed Wi-Fi and a Sonos system, ensuring your beach playlist is always on point. The kitchen, a haven for the culinary curious, features top-tier appliances, making every meal an event.

From the owner:

Tropical Private Island retreat, private beachfront and boat dock – Simply Unmatched – Boat access only.

If you see your dates are unavailable, please inquire and let us customize your perfect vacation experience.

Set on 2 acres of land on a private island, this award winning custom home will provide an island vacation experience for you and your family like no other.

Residential Rental Cert. RRR-00843.2023

The house has 4 bedrooms and 4 bathrooms and an outdoor shower. All rooms view out to Longboat Pass, with 300 feet of beachfront, palm trees, and private dock. Sunsets are spectacular. Great boating water and use of paddle boards, and kayaks. The two upstairs 2-room bedroom suites sleep up to 5 each, and all bedrooms open onto decks. The Master deck has a claw-foot tub with hot and cold water. The house opens on both the east and west side with 4 pocketing 12 foot sliding doors opening onto large screened decks for lounging and dining. Fully equipped kitchen with Sub-Zero, Wolf and Kitchen Aid Appliances. Sound system with IPad/IPhone docking and High Speed WIFI. Surrounded by fine-dining, one of the prettiest beaches and amazing fishing, there is plenty to keep you busy – or swing in the hammocks and order Pizza to be delivered.

Stephen and Catherine are available at 941-928-7991 for any questions throughout your stay.

38 acre private island. We designed and built the home for family and friends to getaway and unwind in a tropical location, yet close to home in Sarasota Florida.

The house faces west for spectacular sunsets. You are surrounded by pristine glassy green gulf boating and swimming water & the best gulf and bay fishing on the west coast of Florida. You will have use of 4 stand up paddle boards, 2 double person kayaks, 2 children’s kayaks and a canoe. We also have a large variety of beach toys, rafts and floats.

Guest reviews about this Private Island Beachfront Home Airbnb On AMI

The “Private Island Beachfront Home” in Longboat Key, Florida, stands out with an exemplary overall rating of 4.95 stars from 21 reviews. This exceptional property, accessible by boat only, offers a unique retreat on a private island, boasting a stunning beachfront, a private dock, and an array of water sports equipment for an unforgettable stay.

Here’s a summary of guest ratings across various aspects:

• Cleanliness: 5.0 stars, indicating a spotless and well-maintained environment.
• Accuracy: 4.9 stars, showing that the property closely matches the description, with slight room for improvement.
• Communication: 5.0 stars, highlighting the host’s prompt and clear communication.
• Location: 5.0 stars, underscoring the property’s prime, private island location.
• Value: 4.8 stars, suggesting guests found the experience to be of excellent value for the cost.

Guests have lavished praise on the property for its beautiful design, private and serene location, and the abundance of activities available right from the doorstep, including paddleboarding, kayaking, and enjoying the private beach. The home’s outdoor amenities, such as the zip line, outdoor shower, and fire pit, alongside its beautiful sunsets and wildlife sightings, were highlights for many visitors.

Stephen, the host, is commended for his responsiveness and helpfulness, ensuring guests have everything they need for a comfortable stay. This property is celebrated as a perfect getaway for families and groups looking to immerse themselves in nature while enjoying the comforts of a beautifully appointed home, making it one of the most beloved homes on Airbnb based on ratings, reviews, and reliability.

Getting The Best Deal

This Private Island Beachfront Home on VRBO looks like the ultimate escape. However, HiChee revealed I could save $3,038 by booking it on Airbnb instead. Time to pack those bags and dive into some serious savings!

Bonus Property

AMI Rental With Heated Pool Near Twin Dolphin Marina

Riverhouse Retreat

Location: Bradenton, Florida

Last, but not the least, Riverhouse Retreat remixes Old Florida charm with a sleek modern twist. Steps from Pier 22, this spot is your front-row ticket to the marina’s buzz, epic eats, and cultural beats. Think less tourist trap, more authentic map to the soul of the area, with Anna Maria Island’s sandy escapades just a short ride away.

The property is a masterpiece of renovation where history meets today’s bougie standards. With room for the whole squad (or two), it boasts that rare blend of communal vibes and nooks for solo chill.

Outdoor life here is no afterthought. This chic home also features a saltwater pool that’s all about that float life, and a porch where rocking chairs and hammocks spell out relaxation in capital letters. Inside, five bedrooms offer dreamy sanctuaries, linked by Jack n’ Jill baths that keep everyone connected yet comfortably apart.

Loaded with perks, from beach gear to a coffee & tea bar, it’s decked out to ensure your stay is less about the hassle and more about the experience.

From the owner:

Riverhouse Retreat, Two King Beds, renovated Old FL home.

-Steps to Pier 22 Restaurant, Twin Dolphin Marina, Oak & Stone Rooftop Dining, Pubs, Ice cream, Bishop Museum, Manatee Rehab, Arts, Shops, Festivals & Riverwalk.

-4 miles to IMG, 7 miles to Anna Maria Island/Holmes, Bradenton & Coquina Beaches.

-Private heated pool & screened deck. Southern Front Porch. Off street 4 car parking. Great for two families, friends, wedding groups, extended families, dedicated office for business travel

Beautifully restored antique heart of pine floors & original staircase. Spacious rooms 10’ ceilings. Original fireplace now converted to electric for safety. 5 Bedrooms: 3 up (share Jack n Jill bath)and 2 down (share Jack n skill bath)are all upstairs and downstairs on one side of the house. Additional full bath off kitchen. Game alcove (board games, cards, kids games) & reading nook. 4 TVs plus DVD. Gorgeous front porch-rock or nap on the hammock. NEW! heated, saltwater pool, bikes, beach chairs, cooler and umbrella! Loads of amenities-travel soaps and shampoos, coffee & tea bar, dishwasher & laundry pods, paper products, so much more!

The entire property with the very large historic home with 5 beds/3 full baths, the screened deck with pool, the front porch and front yard, spacious side driveway easy to park 4 cars, a portion of garage for the bikes, beach equipment and grill we provide.

Guest reviews about this vacation rental

The “Heated Pool-Riverwalk-D’Town-Walk to Restaurants” home in Bradenton, Florida, is a standout Airbnb property with an impeccable overall rating of 5.0 stars from 55 reviews. This beautifully renovated home, cherished for its blend of historic charm and modern amenities, offers guests an exceptional stay with easy access to local attractions.

Here’s a breakdown of guest ratings across key areas:

• Cleanliness: 5.0 stars, signifying that the property is exceptionally clean and well-maintained.
• Accuracy: 5.0 stars, indicating that the property matches or exceeds the expectations set by the listing.
• Communication: 5.0 stars, highlighting the host’s effective communication.
• Location: 5.0 stars, emphasizing the home’s prime location close to restaurants, Riverwalk, and downtown Bradenton.
• Value: 4.9 stars, suggesting guests found the experience to be nearly perfect in terms of value for the cost.

Reviewers consistently praise the property for its beautiful restoration, spacious and comfortable rooms, and the host’s attention to detail, including a heated pool, ample amenities, and a well-equipped kitchen.

The home’s location is a major draw, with guests appreciating the short walks to dining, entertainment, and scenic views along the Riverwalk.

Randy, the host, is lauded for his responsiveness and dedication to ensuring a memorable stay, making this property a favorite among families, groups, and those seeking a blend of relaxation and local exploration. With its unique charm, comprehensive amenities, and exceptional ratings across all categories, this Bradenton home stands out as a top choice for Airbnb travelers.

Getting The Best Deal

Looking for a stylish stay near Anna Maria Island? Look no further than the Riverhouse Retreat on VRBO. But wait, don’t hit that book button just yet! I checked on HiChee and found this gem listed on Airbnb for $201 less for my dates and guests. Discover these exclusive deals using HiChee!

Things to do on Anna Maria Island, Florida

To wrap things up, in this video, we’ll be your Anna Maria Island Travel Guide as we show you eight of the Top Things to do on Anna Maria. Whether you’re looking for food, drinks, shopping, or relaxation, we got you covered. And will even show you the best way to get around on this beautiful island as well.