House vacation rentals in Anna Maria Island

Find and book unique houses on Airbnb

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Popular amenities for Anna Maria Island house rentals

House rentals with a pool

Guest favorite
An aerial view captures a spacious backyard featuring a rectangular pool surrounded by lounge chairs. The property is framed by green lawns and trees, with a covered patio area visible nearby. The home is situated in a quiet cul-de-sac.
Home in Tampa
4.89 out of 5 average rating, 149 reviews

Pool Oasis | Karaoke | 5G | Theater 135" | Grill

NiaghaRating, 5 stars1 week ago
Everything was just like the listing stated. Easy access to everything and plenty to do in the house itself. Its funny but they have notes posted around the house with different instructions or just to let you what light switches you are using. Only problem I had, I couldnt beat PAC MAN!!!!!! WOULD definitely recommend!!
Top guest favorite
A clear blue pool is featured, with sunlight reflecting off the water's surface. The pool is surrounded by a light-colored deck, providing space for relaxation. A set of steps leads into the pool, and a safety fence is visible, ensuring security.
Home in Bradenton
4.98 out of 5 average rating, 57 reviews

IMG Academy-Modern Home Heated Pool Beaches 8 min

LeahRating, 5 stars3 days ago
Andrew was a very helpful and responsive host. The house was beautiful, clean and has described. we love Bradenton and will be back. Neighborhood was nice and quiet and location provided easy access to other areas.
Superhost
A spacious outdoor dining area features a large table surrounded by six chairs, positioned on a light blue surface. In the background, a crystal clear pool reflects sunlight, while an umbrella provides shade. A fenced perimeter and greenery enhance the setting's privacy.
Home in Sarasota
4.93 out of 5 average rating, 135 reviews

Centrally located oasis.

JacobRating, 5 stars9 months ago
The place was mostly what it said it would be, the pictures are accurate. Was pretty nice and cozy. Had lots of privacy, which was really nice. House was clean and had all of the amenities that were promised. Bed was really comfortable. The only drawback was that the pool was a little dirty, looked like it hadn’t been cleaned for a few days before we got there but it wasn’t that big of a deal.
Top guest favorite
A private pool is visible, featuring a heart-shaped design and surrounded by a smooth concrete patio. Sunlight reflects off the clear blue water. Lush greenery and a small garden border the area, with a barbeque grill positioned nearby. The house is partially shown in the background.
Home in Seminole
4.92 out of 5 average rating, 113 reviews

4 bedroom and private pool, near to Clearwater

AprilRating, 5 stars2 weeks ago
This was by far the best day we've had with Airbnb so far!! The house was so perfect for the price and the little amenities were so nice! They had yard games for kids to play and extra blow ups for the pool it was just such a lovely experience. The host was very responsive and understanding for adjustments that needed to be made or giving information I really enjoyed this stay!!
Superhost
Home in Seminole
4.88 out of 5 average rating, 143 reviews

Huge & Heated Pool Home 5 Minutes Away from Beach!

ChantelRating, 5 stars4 weeks ago
We stayed at the property for about 5 days over Spring Break. The location of the house is great but you will need a rental car to get around, many beaches, restaurants and other attractions within minutes of the home. We had small children in our group so we appreciated the gated backyard and the high lock on the sliding door in the back to get to the pool. There were plenty of towels and laundry detergent so we could wash them throughout our stay. The kitchen was pretty well equipped for our needs. Luckily, we bought some cheap plastic cups for the kids to use while we were there and we had paper plates. There was limited to no plastic wear or mixing bowls. Place was clean and lots of toiletries provided. There were no blackout curtains on the windows (usually helpful for small kids/babies nap times) We brought our own travel suction cup kind so that wasn't an issue. The thermostat was brand new but we had no idea how to work it - just call them, they're really helpful and responsive
Guest favorite
A private heated pool is surrounded by a spacious deck featuring lounge chairs and an umbrella-shaded dining area. Lush greenery and decorative plants enhance the outdoor space, creating a relaxing spot for leisure and enjoyment.
Home in Clearwater
4.88 out of 5 average rating, 173 reviews

Poolside Bliss in Clearwater! Heated-pool/Spa

CarmenRating, 5 stars3 weeks ago
This was a great place for me and my family. She was very kind ! Definitely would stay here again …..
Superhost
An inviting saltwater pool is surrounded by a screened enclosure, providing a clear view of the tranquil water. Light dances on the surface, reflecting from overhead lights. A small area for lounging is visible alongside the pool, enhancing the outdoor space.
Home in Bradenton
4.87 out of 5 average rating, 291 reviews

Large 4 bedroom pool home tiki bar close to Ami

JohnRating, 5 stars2 weeks ago
We were able to book a 3 night stay last minute and the hosts were super easy to work with. The house was more than we needed and everything available to make our stay enjoyable. They were quick to respond and answer questions. House is super clean and location allowed us to get to the beach and away from it when needed. We appreciate the space that allowed us to relax and unwind after a busy week.
Guest favorite
A heated pool is set in a tranquil outdoor area surrounded by lush palm trees and tropical plants. Comfortable lounge chairs are positioned nearby, and a colorful pool float is seen resting on the water's surface. A paved patio area provides ample space for relaxation.
Home in Largo
4.95 out of 5 average rating, 134 reviews

Beautiful Heated Pool house, 10 mins to the beach!

LorettaRating, 5 stars1 month ago
The home was exactly as described. The backyard is truly an oasis, very private and peaceful. The pool was wonderful and heated to a comfortable temperature. Grocery stores and restaurants close by. A short drive to Clearwater and St. Petersburg, Anna is a wonderful host, very pleasant, helpful and responsive.

Weekly house rentals

Guest favorite
The welcoming exterior of a historic home is showcased, featuring a gray brick façade and a decorative wreath on the front door. Two large windows flank the entrance, allowing natural light to illuminate the porch area, which is adorned with lush plants and greenery.
Home in Tampa
4.86 out of 5 average rating, 118 reviews

Seminole Heights Gem

JessicaRating, 5 stars1 month ago
We absolutely loved our stay in this house!! Our main priority was separate bedrooms for our teenage son and our preteen daughter to have their own space and this house was perfect!! The rooms were very good size and the master bed/bath was HUGE!!! The beds were very comfy and we loved that the fridge had ice and a water dispenser! We had a little hiccup when originally checking into the house with the passcode not working, but Hannah responded to my message almost immediately, even with it being late at night, and got us into the house in no time!! We would definitely recommend and would love to stay here again on our next trip down to Tampa!!
Top guest favorite
An enclosed swimming pool area features a clear, inviting water surface. Decorative plants line the perimeter, and artistic wall murals add a touch of character. The overhead screen provides shade while retaining an open-air feel, enhancing the tranquil environment.
Home in Largo
4.95 out of 5 average rating, 116 reviews

Slice of Life, pet free heated pool 10 min 2 beach

AprilRating, 5 stars1 week ago
I really enjoyed my stay here! Kim & Bob left homemade cookies which was such a nice touch. The house had everything we needed during our stay and more. They had the perfect essentials for the pools and the beach trips. I would definitely stay here again.
Superhost
A Ranch-style house with a warm-toned exterior is featured. A concrete driveway leads to a single-car garage. Lush green landscaping surrounds the front yard, where trees provide shade. The entrance is marked by a welcoming door, complemented by windows that allow natural light.
Home in Bradenton
4.83 out of 5 average rating, 258 reviews

Comfortable & modern house in Central Bradenton

DesireeRating, 5 stars1 week ago
1. My stay at this Airbnb in Florida was great from start to finish. 2. The place was very clean and well-kept, just as described. 3. I didn’t experience any problems during my stay. 4. The host was responsive and always replied in a timely manner. 5. I would definitely stay here again and recommend it to others.
Top guest favorite
A welcoming living area presents two brown sofas arranged around a coffee table. Exposed wooden beams accentuate the ceiling, while natural light enters through large windows. A subtle area rug adds comfort, and a plant sits on the table, enhancing the open atmosphere of the space.
Home in Sarasota
4.95 out of 5 average rating, 165 reviews

Wood Street Retreat 4/2 Near Beaches & Downtown

JasonRating, 5 stars2 weeks ago
The place was great and very well located, easy to get around town. Very clean, plenty of space, and Wanda was extremely helpful and responsive. Highly recommend
Top guest favorite
A serene outdoor pool area is surrounded by lush greenery and mature plantings. Several lounge chairs with side tables are positioned around the curved, heated pool, offering ample space for relaxation. A screening encloses the area, ensuring privacy and comfort.
Home in Sarasota
4.93 out of 5 average rating, 69 reviews

The Happy House - Seeing is Believing!

EmilyRating, 5 stars3 days ago
We absolutely loved everything about our stay! The house was a perfect fit for our family. The layout was great, comfortable rooms, kitchen was complete with everything you need for cooking. Our communication with Sheila was excellent. Will definitely come back again! Thanks for helping us enjoy a wonderful Spring Break!
Guest favorite
The open-concept living area features a comfortable arrangement of a dark couch and a brown loveseat, centered around a wooden coffee table. A large television is positioned against the wall, and a dining area with four chairs is visible in the background near a window.
Home in Largo
4.83 out of 5 average rating, 40 reviews

The A.G.E House Minutes to West Fl. beaches

JohnRating, 5 stars1 month ago
Cute place! Place was very clean, had all the amenities we needed, and comfortable. Easy to find and in peaceful neighborhood. Perfect for families or groups of 2-4 people. Ashlee was a great host and very responsive. I made the mistake of leaving a small bag behind and she worked with me to get it returned - thanks so much Ashlee I appreciate you!
Guest favorite
A vibrant red flamingo-shaped mailbox is positioned at the front of the property, surrounded by lush palm trees and tropical plants. The pathway is lined with white stone, leading toward the well-maintained house in the background.
Home in Holmes Beach
4.9 out of 5 average rating, 58 reviews

Sea Glass Cottage

MadisonRating, 5 stars3 weeks ago
We loved our stay at Mike and Wendy’s bnb. Fantastic location with walking distance to the beach, the kids loved the pool which was kept very clean. The house was clean and comfortable, very home-y and did not feel like a rental, it felt like you were staying with a friend who lived there year round. Each room has its own bathroom which was very nice!
Top guest favorite
A bright bedroom features a gold metal bed frame draped with a decorative seashell-patterned blanket. A blue-and-white 'Seaside' pillow rests on the bed, alongside a contemporary bedside table with a geometric lamp and a small succulent plant. Sheer yellow curtains allow natural light to filter in.
Home in Sarasota
5 out of 5 average rating, 19 reviews

Elegant Newly Remodelled Spacious HOME

SharonRating, 5 stars1 month ago
We loved this house, high end appliances and furniture! Everything was squeaky clean and very organized! Will definitely be back!

Private house rentals

Superhost
A serene outdoor space features a sparkling pool enclosed by a screened patio, allowing for comfortable relaxation. Two lounge chairs offer seating near the water, while tropical plants surround the area, enhancing the inviting atmosphere. A colorful float is placed in the center of the pool.
Home in Bradenton
4.95 out of 5 average rating, 38 reviews

Now Booking for Summer - heated pool & grill!

DrewRating, 5 stars2 months ago
House was spotlessly clean and well maintained. We were really only sleeping there so did not use pool or backyard amenities. Would highly recommend. Only suggestion would be to have coffee and coffee condiments available on check in. Most Air BNBs I have stayed at offer this amenity.
Guest favorite
The exterior of the house is shown, featuring a single-story structure surrounded by lush greenery. Palm trees and ornamental plants add to the landscape. A spacious lawn is visible in the foreground, along with a two-car garage on the right side of the building.
Home in Sarasota
4.97 out of 5 average rating, 58 reviews

2223 Doud Street, Sarasota, FL

MicheleRating, 5 stars1 month ago
This home was perfect for our group. We loved having 3 en-suite master bedrooms. The location is great for beach(Siesta Key), waterfront restaurants and shopping. We would definitely book again!
Superhost
The exterior of the house is showcased, featuring a combination of light stone and bold pink accents. A spacious driveway leads to a two-car garage, while a well-maintained lawn with greenery complements the inviting entrance.
Home in Largo
4.79 out of 5 average rating, 425 reviews

Spacious Home Solar-Heated Pool and Spa

ValerieRating, 5 stars2 weeks ago
Great value!! We loved the pool area and very quiet neighborhood!
Guest favorite
Home in Largo
5 out of 5 average rating, 10 reviews

Poolside Paradise, Near Beach

LindseyRating, 5 stars3 weeks ago
A perfect home for our family to stay at! The pool was amazing, the linens were the most comfortable I’ve ever had and the house had great amenities. Thao was responsive and helpful.
Top guest favorite
A covered patio area is viewed, featuring seating arrangements with comfortable couches and a table, illuminated by string lights overhead. A saltwater pool is visible in the background, surrounded by a safety fence, enhancing an inviting outdoor space.
Home in Sarasota
4.9 out of 5 average rating, 41 reviews

Sea la Vie - heated pool, 4b2b, stocked kitchen

JisungRating, 5 stars1 week ago
Great place for relaxing get together with friends. Pool and outdoor area was simply amazing. Close by the beach and downtown sarasota!
Superhost
A serene saltwater pool reflects the surrounding palm trees and evening sky. Lounge chairs are positioned along the deck, offering comfort beside the tranquil water. The dock is visible in the background, enhancing the waterfront ambiance.
Home in Longboat Key
4.88 out of 5 average rating, 120 reviews

Summer House longboat key

AndreaRating, 5 stars2 weeks ago
We had a wonderful stay at Chris’s house on longboat key! The pool was so nice for the kids and us adults to swim and relax by. The house was very nice and the beds were very comfortable. There were plenty of towels, extra sheets, and the kitchen was very well stocked with pot and pans. We did find it easier to drive closer to the crosswalk to the beach and park before walking across the street to get to the beach access. The beach was very quiet and beautiful. We found so many shells and our kids loved doing evening swims at sunset! It’s a very quick drive to Anna Maria Island and St Armand’s Circle. We really enjoyed our stay.
Guest favorite
A spacious living area features two brown leather sofas and two chairs, all adorned with decorative pillows. A coffee table with a fish centerpiece is positioned in the middle. The open layout connects to a dining area, visible in the background.
Home in Largo
4.91 out of 5 average rating, 58 reviews

Walk to Beach Food Drinks & Shops! “The Big House”

HillaryRating, 5 stars1 week ago
This house was an amazing stay! Jeff and Lynne are amazing host as usual and I even had the pleasure of meeting them both this time. I’d there is anything you may need or even questions they are very responsive and helpful. The house is close to the beach and restaurants with a Publix and even a mall about 5-15 up the road. The house had everything I needed to enjoy a peaceful and relaxing vaccination. They even have necessities for the beach. The setup of the house is spacious which I really loved. Can’t wait to hopefully stay again.
Guest favorite
A well-furnished living area features a light-colored sofa with decorative pillows, a glass coffee table, and an area rug with subtle patterns. A dark wooden entertainment unit holds a television, and natural light filters in through nearby windows, enhancing the serene ambiance.
Home in Largo
4.81 out of 5 average rating, 80 reviews

Tranquil Home. 2 minutes to Indian Rock Beach...

TerrenceRating, 5 stars4 weeks ago
Gisele's place was clean and just like the pictures showed. The pool area was nice with a large Weber grill and lots of chairs . There were plenty of pool rafts in the garage for our use. Grocery stores, liquor stores, and restaurants all within a short drive and some within walking distance. The neighborhood was friendly and quiet and had a Catholic church within a 2 minute walk. We would definitely consider staying again!

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