House vacation rentals in Anna Maria

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Popular amenities for Anna Maria 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 stars2 weeks 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!!
Guest favorite
The screened-in pool area features a clear, inviting swimming pool surrounded by a spacious deck. Natural light filters through the screen, highlighting the lush greenery visible in the background, creating a tranquil and private atmosphere.
Home in Sarasota
4.97 out of 5 average rating, 59 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!
Top guest favorite
The outdoor living area features a heated pool surrounded by stone-tiled decking. Lounge chairs are positioned nearby, offering relaxation under a shaded roof. A BBQ grill is visible, complemented by greenery and comfortable seating in the background, creating an inviting space for gatherings.
Home in Tampa
5 out of 5 average rating, 8 reviews

(HGR) Poolside Paradise: Airbnb Retreat

ShannonRating, 5 stars1 week ago
We had a great stay!! The house was clean and comfortable and spacious for our family. Vildana was very responsive when we needed anything and was easy to get in touch with. We would love to stay again!
Guest favorite
A screened enclosure surrounds a saltwater pool, featuring a light-colored stone deck and a shaded area with exposed wood beams. The backdrop includes a modest house and green landscaping, creating a serene outdoor setting.
Home in Sarasota
4.94 out of 5 average rating, 98 reviews

Beautiful heated pool home, minutes from beaches

KatarzynaRating, 5 stars1 month ago
Great host and house. We enjoyed the layout of the house, awesome kitchen but the most we enjoyed the outside space and pool. Very nice neighborhood for walks in the morning. Easy drive to beaches, quick drive to grocery stores and restaurants.
Superhost
Home in Seminole
4.88 out of 5 average rating, 145 reviews

Huge & Heated Pool Home 5 Minutes Away from Beach!

RoxanaRating, 5 stars2 weeks ago
great place recommended .
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 stars1 month ago
This was a great place for me and my family. She was very kind ! Definitely would stay here again …..
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.
Guest favorite
Home in Land O' Lakes
4.86 out of 5 average rating, 125 reviews

Delightful elegant lake home

EdenRating, 5 stars1 week ago
Calvin’s place was a wonderful find! The best part was the bird island in the lake behind the house - we really enjoyed listening to the birds and watching them nest and fish. The beds were comfortable, garage parking was easy, and the location was excellent. The pool was beautiful and the kids loved it (it was too chilly for the grownups). Check in was super easy and when we ran into a snag with a broken coffee maker, a new one was delivered right away. We had a lovely stay and would definitely book again.

Weekly house rentals

Superhost
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, 120 reviews

Seminole Heights Gem

MaryRating, 5 stars2 weeks ago
Captain’s place suited our needs. The location worked well with easy access to shops, and restaurants. The place was clean and comfortable with comfortable furniture. A heads up that Captain does not provide any bath soap, shampoo or conditioner. The sheets are nice, 100% cotton, towels are good quality and plentiful. The kitchen is moderately well stocked for preparing meals. The air conditioner worked well. The outdoor spaces are sparsely furnished and not particularly welcoming. There are two large food trucks parked adjacent to the back yard and there was one chair on the deck outside the master bedroom. Overall, it was a pleasant stay.
Guest favorite
A screened-in area features a heated salt-water pool surrounded by tropical plants. Two lounge chairs are positioned nearby on a tiled surface, offering a relaxing space while sunlight filters through the mesh enclosure.
Home in Venice
5 out of 5 average rating, 8 reviews

Pool - Tropical Retreat! Minutes to local Beaches!

RisaRating, 5 stars6 months ago
Olga’s listing was a perfect home for workcation. Has an office room, looks exactly the same from the picture, very clean, and they’ve got everything you need if you plan to cook. I take sleepy seriously and curtain kept room nice and dark in the morning. Movable shower head and instapot were added bonus for us where we were able to cook rice. Pool was super clean despite hurricane hits hard in the area, too. There has been minor issues here and there due to Hurricane Milton but Olga was very attentive and always promptly helped to solve the issue. Highly recommend to rent it if you plan to be in the area.
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 stars3 weeks 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, 166 reviews

Wood Street Retreat 4/2 Near Beaches & Downtown

SteveRating, 5 stars4 days ago
I always enjoy a bargain and for the going prices of a comparable hotel room with less accommodations this was a great deal. The place was immaculate and when I thought we were missing towels the host was ready to get them there immediately. It felt like I was home and I appreciated the care and cleanliness that made the stay exceptional. Thoughtfully provided a pack and play for my grandchildren. There was nothing lacking. Everything first class and top quality. Highly recommend this home and the host to any future tenant.
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 Indian Beach-Sapphire Shores
4.93 out of 5 average rating, 69 reviews

The Happy House - Seeing is Believing!

EmilyRating, 5 stars1 week 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
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 stars1 month 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!
Superhost
A spacious living area features a large sectional sofa and a mounted television, with natural light filtering in through the wide windows adorned with light curtains. A modern kitchen bar with stools is visible in the foreground, providing an open layout for easy movement.
Home in Sarasota
4.75 out of 5 average rating, 4 reviews

Amazing Location! Amazing Amenities!

JoniRating, 5 stars1 month ago
Jennifer offered a beautiful, clean home that was as described and perfect for our family! She was very accommodating and quick to respond! Our family enjoyed all the home and resort had to offer and can’t wait to book our next vacation using one of Jennifer’s properties!

Private house rentals

Top guest favorite
A two-story house is set among lush greenery, featuring a welcoming porch with black railings. Vibrant pink flowers hang from a planter, adding a touch of color. The open space underneath the house provides parking options, surrounded by trees and landscaped grounds.
Home in Plant City
4.99 out of 5 average rating, 529 reviews

The Strawberry Field Stilt House

BrittanyRating, 5 stars1 week ago
Wow!! This home is so beautiful and comfortable. The host has put time and attention into all the details. The landscaping is amazing, so many tropical plants and well maintained. The home itself is comfortable, from the bedding and beds themselves to the small details and amenities the host provided. We did not want to leave and are already booking again when the strawberries are in season, highly recommend this Airbnb!
Top guest favorite
The entrance of the home is framed by lush greenery and vibrant flowering plants. The façade features large windows that provide ample natural light, while a covered porch welcomes guests. A clear blue sky complements the fresh and inviting exterior.
Home in North Port
4.79 out of 5 average rating, 152 reviews

3 bdrm Pool Home / Quiet Cul De Sac

JeffRating, 5 stars1 week ago
Very nice home, plenty of space for larger family. We used the heated pool everyday. Stores within 5-10 driving minutes of property. Would definitely rent in future
Superhost
A spacious screened patio features a glistening pool surrounded by tropical plants. A pink flamingo float and two beach balls add a playful touch to the water. Two lounge chairs are situated nearby, perfect for relaxation under the bright blue sky.
Home in Tampa
4.92 out of 5 average rating, 98 reviews

The Breeze-private (optional) heated pool house.

MelvynRating, 5 stars1 week ago
We definitely recommend staying here!It's a beautiful apartment in what seems like a nice neighborhood. We were there for 5 days and the neighbors were quiet and the neighborhood felt safe and comfortable. The swimming pool was fantastic, great yard for the kids to play in, pool table was fun to have.
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, 121 reviews

Summer House longboat key

DaneRating, 5 stars5 days ago
Chris was a very responsive host. During our stay he spent a day working on his boat in the back. He was very friendly, but also respected our privacy. The house met all of our expectations and our kids loved the pool. The neighborhood was great to walk through and each house offered fantastic curb appeal. With 3 kids under the age of 6, the 10-12 minute walk to the beach was a little long, but Chris’ wagon and beach supplies helped! The golf cart would have been ideal, but without a place to park near the beach we didn’t have much use for it. We thoroughly enjoyed our stay and the entire family agrees we’d love to go back. Thanks Chris!
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, 81 reviews

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

KathrinRating, 5 stars1 week ago
We spent 2 weeks in Gisele’s home…it was exactly as described. We really appreciated the outdoor space/patio. We enjoyed our morning coffee, utilizing the large bbq and outdoor dining area and ending our days with a nightcap in the enclosed patio. The location was great, centrally located with easy access to beaches from Clearwater to St. Pete’s. We will definitely return when back in the area again. Gisele is a great host.
Guest favorite
A private saltwater pool is surrounded by a spacious patio, featuring an umbrella for shade. Two adirondack chairs are positioned by the pool, while a vibrant orange lounge area invites relaxation. Lush green grass complements the outdoor setting.
Home in Siesta Key
4.92 out of 5 average rating, 115 reviews

Siesta Peace Retreat a private home rental

Isabel CristinaRating, 5 stars9 months ago
Tracy's place is wonderful, and she is very attentive. She gave us lots of tips on what to do and where to go, which was a big plus. The backyard is very relaxing with a lovely spa where we enjoyed the evenings. The house was super clean, and the beds were very comfortable. If I return to Siesta Key, I will definitely stay there again.
Guest favorite
A spacious bedroom is furnished with a plush bed dressed in soft neutral tones and decorative pillows. Two bedside tables flank the bed, each holding a lamp. Natural light fills the room, highlighting the warm color palette and elegant bedding.
Home in Port Charlotte
4.9 out of 5 average rating, 42 reviews

Charming home near the Beach and Punta Gorda.

DebraRating, 5 stars3 weeks ago
We had a great time. Loved the location, it was close to pretty much everything. Our two 4 pound, Emotional Support Yorkie’s loved the screened in lanai. They would go out there to play and to get some warm sunshine. It was really cute! I love the laundry room, it was perfect and so convenient, right outside the lanai! The two bathrooms were really nice… They both were beautifully remodeled. All in all… our stay was great and we enjoyed it very much. Thank you Angel. We appreciate it. Debbie, Bob, Luci, and Tito.
Top guest favorite
A serene outdoor area features a heated pool surrounded by tropical landscaping. Light-colored pavers outline the pool, and large sliding glass doors lead to an inviting sunroom. Towering palm trees provide shade, contributing to the tranquil ambiance.
Home in Holmes Beach
5 out of 5 average rating, 65 reviews

Private Luxurious Ground Level Home

JemimaRating, 5 stars1 week ago
Wonderful stay at this special home. Excellent location. Perfectly laid out and well designed home. Really appreciated the separate patio area to the pool area which was very safe with kids. Walk to coffee, restaurants and beach. Quick golf cart ride around the island. 10/10 recommend!

Quick stats about house rentals in Anna Maria

  • Total rentals

    400 properties

  • Nightly prices starting at

    ﺩ.ﺇ404 before taxes and fees

  • Total number of reviews

    5.7K reviews

  • Family-friendly rentals

    390 properties are a good fit for families

  • Pet-friendly rentals

    130 properties allow pets

  • Rentals with a pool

    350 properties have a pool

Destinations to explore

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