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Vacation rentals with a pool in Sarasota County

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Top-rated rentals with a pool in Sarasota County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost
Home in Gulf Gate Estates

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

Welcome to The Salty Unicorn, your cheerful Sarasota escape just five miles from Siesta Key Beach. This fully renovated 3-bedroom home is designed for relaxation and fun, with a bright open layout, stylish coastal décor, and plenty of space to gather with family or friends. Start your mornings with coffee by the pool, spend sunny afternoons swimming or lounging in the spacious backyard, and end the day with dinner in the screened lanai. Whether you’re here for beach days, family time, or a peace

4.89 out of 5 average rating, 107 reviews
Guest favorite
An outdoor area features a heated pool surrounded by a spacious deck. Lounge chairs are positioned nearby for relaxation, and a dining set offers seating for outdoor meals. A screened enclosure provides protection from insects while allowing natural light to filter through.
Home in Sarasota

Heated 3BR Pool Home Glen Oaks | Close to Downtown

Family-friendly pool home near Bobby Jones Golf Club, perfectly located in the heart of Sarasota. You’re less than 10 minutes from top attractions, dining, and shopping, Downton Sarasota and just a short drive to the world-famous Siesta Beach or Lido Beach. This private home features its own entrance, a heated pool, and a fully fenced backyard—ideal for families and added privacy. We’re pet-friendly too! Comfortable, central, and close to everything—perfect for your Sarasota getaway VR24-00164

4.91 out of 5 average rating, 140 reviews
Top guest favorite
Home in Sarasota

Sunshine House, near Downtown, Legacy Trail, Beach

Great location! This is a family friendly home, close to downtown and beaches, with a pool, fenced yard, and a large, screened porch for lounging and having meals outside. Close to all the great things Sarasota has to offer- museums, gardens, theaters, shopping, Sarasota Bay, and beaches. The house is 1.5 miles from downtown, 10 min to St. Armands, 15 min to Lido Beach, and about 20 min Siesta Key Beach. One dog considered with a fee. Children must be supervised at all times in the pool area.

4.98 out of 5 average rating, 133 reviews
Top guest favorite
A covered patio area features modern wicker furniture with white cushions, positioned around a glass coffee table. The inviting space overlooks a pristine pool, surrounded by a protective screen. Lush greenery is visible in the background, enhancing the tranquil setting.
Home in Sarasota

Luxury Pool Family Oasis-Siesta Key/DT 3BR/2BA

Welcome to your home away from home! This renovated, spacious, and bright pool home will immerse you in a luxurious experience the minute you arrive. Located on a lush, quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in the USA), 10 minutes to downtown (with fantastic restaurants and shopping), and within walking distance of the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake Park, and the new UTC mall!

4.96 out of 5 average rating, 154 reviews
Guest favorite
A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.
Home in Sarasota

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

4.8 out of 5 average rating, 189 reviews
Guest favorite
The exterior of a newly renovated home is shown, featuring a light-colored brick facade and a modern garage door. A well-maintained driveway leads to the entrance, which is accentuated by a bright orange door. Landscaping includes gravel beds and low-maintenance plants amidst partial cloud cover.
Home in Sarasota

Gorgeous renovation with pool, minutes from beach

Light, bright and newly renovated. Beautifully decorated 3 bedroom home minutes from Siesta Key and downtown. The spacious modern kitchen has a slider that leads to covered porch and large pool with private fenced yard. A second slider from the porch leads to the master bedroom with master bath and walk in closet. Open living room and 2 additional big bedrooms make the house perfectly comfortable for 6. Everything you need is right here! Siesta Key Beach Distance - 16 Min; 6.1 Mi

4.88 out of 5 average rating, 103 reviews
Top guest favorite
Home in Sarasota

Heated&Renovated Pool•Beach Retreat•15m to Siesta

Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

4.93 out of 5 average rating, 409 reviews
Guest favorite
A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.
Home in Gulf Gate Estates

Beautifully Remodeled Home with Pool Near Siesta

It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

4.95 out of 5 average rating, 165 reviews
Top guest favorite
Condo in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

4.92 out of 5 average rating, 172 reviews
Top guest favorite
A clean, large pool is surrounded by comfortable lounge chairs. Illuminated in soft purple light, the pool features colorful inflatables, with a gazebo and grill visible in the background. Palm trees frame the serene lakeside view beyond the pool area.
Home in Sarasota

Lakefront Getaway in Sunny FL

Welcome to your lakeside retreat in sunny Florida! Our house offers stunning lake views and spacious, immaculate rooms. Just a short drive to Siesta Beach (#1 in the USA). The main house has 3 beautifully furnished bedrooms. The separate guest house it can be available for an extra fee. Relax by the large, clean pool in our private, gated property. Well-equipped kitchen, gazebo, grill, and family-friendly features await!

4.9 out of 5 average rating, 101 reviews
Top guest favorite
A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.
Home in Sarasota

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

5.0 out of 5 average rating, 110 reviews
Top guest favorite
Home in Sarasota

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

4.98 out of 5 average rating, 130 reviews

Popular amenities for Sarasota County rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.
Home in South Sarasota

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

4.94 out of 5 average rating, 106 reviews
Superhost
A heated saltwater pool is framed by a privacy fence, with lounge chairs positioned nearby. Lush palm trees add greenery to the space, creating an area for relaxation. The clear water reflects the sky, enhancing the tranquil ambiance of the outdoor setting.
Home in Sarasota

~Flamingo House~3 br,3 bath, heated pool~

4.85 out of 5 average rating, 221 reviews
Top guest favorite
A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.
Home in Sarasota

Oasis by Siesta Key Beach and Downtown SRQ w/pool

4.94 out of 5 average rating, 143 reviews
Top guest favorite
Home in Gulf Gate Estates

Coastal Paradise w/ Pool & Dock, Minutes to Siesta

4.95 out of 5 average rating, 128 reviews
Top guest favorite
An outdoor dining area features a wooden table set for four, overlooking a pristine pool. Lounge chairs are positioned nearby, providing a relaxing space for sunbathing. The screened patio ensures comfort while enjoying meals or relaxation outdoors.
Home in Sarasota Springs

Heated Pool Oasis 3BR/2BA near Siesta Key Beach

4.98 out of 5 average rating, 162 reviews
Guest favorite
A modern house is presented with a neatly manicured lawn and a driveway leading to a garage. Lush palm trees and potted plants frame the entrance, while large windows allow natural light to fill the interior. The structure has a welcoming white facade under a gray roof.
Home in Sarasota

Casa Cruz-3RM/2BA w/Heated Salt Water Pool

4.95 out of 5 average rating, 119 reviews
Guest favorite
A well-lit bedroom features a spacious bed with a light-colored bedspread. Two large windows offer views of the outdoors, framed by sheer curtains. A ceiling fan hangs above, providing airflow. A comfortable chair and a dresser add practical elements to the inviting space.
Home in Sarasota

The Palms Away

5.0 out of 5 average rating, 39 reviews
Top guest favorite
Home in Sarasota

Sun Coast Oasis-Heated Pool-Pool Table-Arcade

5.0 out of 5 average rating, 10 reviews

Condo rentals with a pool

Top guest favorite
A bright and airy living space features a modern sofa facing a sleek coffee table. The open kitchen is visible in the background, showcasing white cabinetry and bar seating with stylish stools. Light fills the room through large windows, enhancing the spacious feel.
Condo in Sarasota

Modern Coastal Oasis - Beach and Private Patio

4.96 out of 5 average rating, 165 reviews
Top guest favorite
A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.
Condo in Gulf Gate Estates

Lake View 1BR Condo | Heated Pool Near Siesta

4.89 out of 5 average rating, 198 reviews
Superhost
Condo in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

4.82 out of 5 average rating, 154 reviews
Guest favorite
A serene lanai view features a dining table with chairs overlooking the community pool. Lush palm trees frame the scene, while sunlight reflects off the water's surface. A doorway is visible, leading to the interior of the condo.
Condo in Sarasota

Gateway to Siesta Key - 1/2 Mile to the Beach

4.96 out of 5 average rating, 225 reviews
Top guest favorite
Condo in Sarasota

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

5.0 out of 5 average rating, 109 reviews
Guest favorite
Condo in Siesta Key

5209A Calle Menorca - Siesta Key Village Condo

4.83 out of 5 average rating, 108 reviews
Top guest favorite
Condo in Sarasota

Gulf Views | XL Balcony | Walkable

4.89 out of 5 average rating, 102 reviews
Guest favorite
A light-filled living area features a comfortable white sectional sofa with decorative pillows, complemented by a wooden coffee table. Large glass doors lead to an outdoor space, while a television and two lamps enhance the room's functionality and warmth.
Condo in Siesta Key

The Palm Bay Club on Siesta key Beach

4.84 out of 5 average rating, 126 reviews

Other vacation rentals with a pool

Superhost
The exterior of a single-story home is showcased, featuring a covered entryway with double doors. Lush greenery, including potted palm trees and trimmed shrubs, frames the entrance. A concrete path leads through a pebble-strewn area, offering a welcoming appearance on a sunny day.
Villa in Sarasota

Paradise Villa- Sarasota

4.8 out of 5 average rating, 100 reviews
Top guest favorite
Home in Arlington Park

Sleeps 8, Private Pool Near Siesta Key

4.96 out of 5 average rating, 49 reviews
Guest favorite
A large, heated pool is set within a spacious screened lanai, featuring a light blue floating mat. The pool area is bordered by smooth tile flooring and is complemented by sheer white drapes. A grassy yard is visible through the lanai's screening.
Home in Gulf Gate Estates

Siesta Key-Private Family Pool Home-6 min to Beach

4.83 out of 5 average rating, 63 reviews
Guest favorite
Home in Sarasota

Good Vibrations Home

5.0 out of 5 average rating, 18 reviews
Top guest favorite
Home in Sarasota Springs

GARDEN VIEW HOUSE WITH A POOL

4.98 out of 5 average rating, 96 reviews
Guest favorite
Condo in Sarasota

Charming Poolhouse · 1BR · Close to Siesta

4.97 out of 5 average rating, 67 reviews
Guest favorite
A screened-in pool area is shown at dusk, with a clear pool reflecting the colorful sky. A white fence surrounds the space, and comfortable lounge chairs are positioned nearby, adding to the inviting outdoor atmosphere.
Home in Arlington Park

Heated Pool + Ping Pong | Near Siesta Key Beach

4.91 out of 5 average rating, 77 reviews
Top guest favorite
A modern cottage is set within a spacious, manicured lawn surrounded by trees. A circular driveway leads to the house, which features a dark metal roof and large windows. Lush greenery frames the property, emphasizing its serene outdoor environment.
Cottage in Sarasota

Bee Keepers Cottage

4.97 out of 5 average rating, 75 reviews

Destinations to explore