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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
Top guest favorite
A custom pool is framed by elegant lounge chairs and tropical landscaping. Water features create gentle curves, while illuminated details enhance the space as the sunset casts a warm glow. A covered outdoor area is visible in the background, providing seating and entertainment options.
Home in Sarasota

Fruit /Botanical Garden Estate 2 ml to downtown EV

Indulge at this Mediterranean estate, boasting lush botanical gardens and rare tropical fruit trees for your picking pleasure. Enjoy the custom pool, hot tub, sauna, cold plunge and the home gym. The expansive outdoor haven features a fully-equipped kitchen, fireplace, TV, and dining space. Enjoy leisurely games of pool, ping pong & shuffleboard, then retreat to the luxurious indoors with comfortable beds and a massive TV, all within the privacy of a walled-in estate. Your lavish escape awaits.

4.97 out of 5 average rating, 103 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, 138 reviews
Top guest favorite
The outdoor space is enclosed by a screened lanai, showcasing a heated saltwater pool and a dining area with a large table that seats eight. Lounge chairs and a BBQ grill are positioned near the pool, surrounded by tropical landscaping and a clear blue sky.
Home in Sarasota

3 bedroom Heated salt water pool close to Siesta

Your family will be close to everything when you stay at this centrally-located place. 15 minutes to Siesta Beach, 10 minutes to UTC mall, 15minutes to downtown, 20 minutes to SRQ airport. This home is fully remodeled, fully furnished, sleeps 8. We have 1 king size bed in the master, second bedroom is queen bed, 3rd bedroom is 1 full and 1 twin beds. This is open plan home with a big family room, 60" TV above electric fireplace, formal dining room seats 6 with the bar seats 4. Master has 55"TV

4.97 out of 5 average rating, 116 reviews
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!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

4.94 out of 5 average rating, 100 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, 149 reviews
Superhost
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, 185 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, 101 reviews
Guest favorite
An outdoor dining area features a large table set with plates and glasses, surrounded by seating. A pool is visible nearby, framed by lounge chairs under a covered patio with ceiling fans. The walls are painted in a vibrant blue, enhancing the inviting atmosphere.
Home in Sarasota Springs

Sarasota Sandpiper: 4 Bed/3 bath + Pool

Your Ideal Getaway: All-Inclusive Comfort and Convenience Discover the perfect retreat that's close to everything you desire in a vacation. Whether you're seeking the beach, family-friendly activities, nightlife, mini golf or championship golf courses, you'll find it all at your doorstep. It's a place where you can unwind and savor life's simple pleasures. Embrace the great outdoors with an outdoor space that's perfect for relaxation and enjoyment.

4.91 out of 5 average rating, 202 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, 170 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, 128 reviews
Top guest favorite
A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.
Island in Sarasota

SEPT SALE! Sarasota #1 Luxury Villa! PRIV BEACH!

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

4.98 out of 5 average rating, 367 reviews

Popular amenities for Sarasota County rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

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!

5.0 out of 5 average rating, 107 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, 140 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
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

4.9 out of 5 average rating, 99 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, 116 reviews
Top guest favorite
Home in Sarasota

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

4.93 out of 5 average rating, 407 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
Top guest favorite
Home in Arlington Park

The Blessing House- Htd Pool/Spa, Close to Beaches

5.0 out of 5 average rating, 117 reviews

Condo rentals with a pool

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, 196 reviews
Guest favorite
Condo in Sarasota

LJ's Cottage 2

4.82 out of 5 average rating, 111 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
Superhost
Condo in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

4.82 out of 5 average rating, 152 reviews
Guest favorite
The exterior of the condo features a serene pool area surrounded by tropical landscaping. Lounge chairs are positioned near the pool, with a tiki bar visible in the background, creating a relaxed atmosphere amidst the vibrant palm trees and colorful building.
Condo in Siesta Key

5213A Calle Menorca - Siesta Key Village Condo

4.86 out of 5 average rating, 126 reviews
Guest favorite
Condo in Sarasota

Gulf Views | XL Balcony | Walkable

4.89 out of 5 average rating, 100 reviews
Guest favorite
A serene beach scene captures calm waves gently lapping at the shore under a sky filled with scattered clouds. Soft hues of orange and blue reflect in the water, suggesting an approaching sunset over the tranquil coastline.
Condo in Sarasota

Private Beach | Gulf Views | Pool | Walk to Dining

4.87 out of 5 average rating, 105 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

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
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, 73 reviews
Guest favorite
Home in Sarasota

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

5.0 out of 5 average rating, 16 reviews
Top guest favorite
Home in Arlington Park

Modern Home Heated Pool near Siesta & Downtown

4.96 out of 5 average rating, 46 reviews
Top guest favorite
Home in Sarasota

Modern 4bd | Heated Pool | Hot Tub + Studio Suite!

5.0 out of 5 average rating, 22 reviews
Top guest favorite
A private pool area is enclosed by a screened-in lanai, featuring clear blue water reflecting sunlight. A patio umbrella and several chairs are positioned nearby, surrounded by lush greenery, creating a relaxing outdoor space.
Home in Sarasota Springs

GARDEN VIEW HOUSE WITH A POOL

4.98 out of 5 average rating, 95 reviews
Superhost
Home in Sarasota

Kokomo Keys | Heated Pool + Outdoor fun park

5.0 out of 5 average rating, 4 reviews
Top guest favorite
Home in Sarasota Springs

Private Heated Pool, 8.5mi to Siesta Key Beach

5.0 out of 5 average rating, 21 reviews

Destinations to explore