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Vacation rentals with a pool in South Sarasota

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in South Sarasota

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

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Top guest favorite

An expansive backyard features a private heated pool, surrounded by lounge seating and a well-maintained putting green. Softly glowing twilight casts a warm hue over the space, framed by lush greenery and a serene atmosphere.

Home in Sarasota

5 out of 5 average rating, 102 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream! From the swings at the dining room table and the neon sign, to the moss wall and the private putt-putt course, Living the Dream is fully loaded and is the ultimate luxury vacation home! Located just 15 minutes away from BOTH Lido Key and Siesta Key Beach, this incredible stay includes: ✔ Backyard Putt-Putt Course ✔ Private Heated Saltwater Pool w/ Lounge Chairs ✔ Covered Patio w/ String Lights ✔ Jura Espresso Machine ✔ 65" Frame TV w/ Youtube TV Included!

A covered outdoor dining area is featured, furnished with a round table and four cushioned chairs. The space is positioned adjacent to the private pool, surrounded by a screened enclosure that allows for natural light and a view of the pool.

Bungalow in Sarasota

4.91 out of 5 average rating, 351 reviews

Pool & fenced-in yard in downtown edge bungalow

This 2 bed-2 bath house is a homey Florida bungalow with wood floors and lots of natural light, located in a quiet neighborhood on the downtown core edge. Enjoy a spacious and private, fenced-in backyard with pool, covered grill and eating area. The home is minutes away from the Legacy Trail, the new Bay Park, Payne Park, dining, live music, bars, theatres, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

A screened-in patio surrounds a refreshing pool, reflecting the sky above. Outdoor seating is visible, providing a space for relaxation. The adjacent house is shown in a light blue hue, with a door leading to the interior and a shed partially seen. Lush greenery can be observed in the background.

Home in Sarasota

4.95 out of 5 average rating, 492 reviews

The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

Top guest favorite

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

Guesthouse in Sarasota

5 out of 5 average rating, 206 reviews

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

An indoor pool is enclosed within a screened area, offering a clear view of tranquil blue water and surrounding trees. Comfortable outdoor seating is visible, complemented by a sunlit patio space. Large glass doors provide access to the pool area, enhancing the open feel.

Home in Sarasota

4.96 out of 5 average rating, 133 reviews

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

Top guest favorite

A caged outdoor pool is surrounded by lush tropical greenery. A floating mat is centered in the clear water, with sunlight filtering through the overhead screens, casting dappled shadows. Lounge chairs are arranged nearby, and a vibrant umbrella offers shade.

Guest suite in Sarasota

4.94 out of 5 average rating, 336 reviews

Beach & Town Posh Location! Jungle Paradise Studio

PRIME Town/Beach 3.2 miles location! *Private Studio* Access Non shared Pool. Studio w/private entrance & private patio @Designers private Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Beach, shops, dining, & 5mins/Downtown Sarasota. Walk/local markets/ dining/movies & shopping New King bed. New 50" TV. Off street parking. No Smoking/Vaping! Wet Bar, No kitchen, lite meals only! No hotels in my exclusive area! Live like a local!

A bright and airy indoor space features a coastal-themed rug with a starfish design. Light-colored furniture and a wooden table provide a casual dining area, while large windows allow natural light to fill the room and offer views of the backyard.

Home in Sarasota

4.93 out of 5 average rating, 359 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

- Located in a quiet Sarasota neighborhood minutes from shopping, restaurants, & Siesta Key, this amenity packed home is perfect for families and beach enthusiasts! - Enjoy the heated pool and comfy outdoor furniture in your fenced in backyard where you can bask in the sun swimming and grilling. - Beautifully designed coastal interior w/ new appliances, Smart TVs, and fast WiFi. - Your on-site Superhost is available if needed to assist with making your stay enjoyable and worry free.

A private pool is surrounded by a paved area, featuring two lounge chairs positioned near the water. Green foliage adds a natural touch, while a white fence encloses the space, creating a secluded atmosphere. The clear blue water reflects the sky, inviting relaxation.

Cottage in Sarasota

4.94 out of 5 average rating, 127 reviews

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Enjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures.

A clear blue swimming pool is surrounded by a brick patio, with lounge chairs positioned nearby. Lush palm trees and greenery are visible in the background, providing a serene atmosphere. The pool's inviting water reflects the bright blue sky above.

Condo in Sarasota

4.87 out of 5 average rating, 115 reviews

Anchor house +6 min. from Siesta Beach+heated pool

★ "Ground floor 1 bedroom 1 bathroom apartment" ★ "An incredible apartment and 6 star hospitality!" 🌴 Stylish Retreat Near Siesta Key Heated Pool! Welcome to your perfect Sarasota getaway! This 600 sq. ft. pet-friendly home offers a heated pool access, and a prime location just 6 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.

A sparkling pool is surrounded by neatly arranged lounge chairs on a stone patio. The building nearby features multiple balconies and large windows, allowing natural light to filter through. Lush greenery and palm trees enhance the area, creating a relaxing outdoor setting.

Apartment in Indian Beach-Sapphire Shores

4.96 out of 5 average rating, 140 reviews

Free Early Chk-in, Super Clean, Free Parking,Bikes

Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb property on the main road 1 mile from downtown Sarasota. Discover over 60 enticing amenities, from a secure room safe to a luxurious, indulgent bed. Just a stone's throw away from downtown Sarasota, Lido Beach, and essential amenities like grocery stores and pharmacies, our corner apartment with a dazzling wrap-around patio is your perfect hideaway. Bicycles at your disposal. Book now

A heated pool with a vivid blue surface reflects sunlight. Two bright blue lounge chairs sit invitingly at the pool's edge, surrounded by a spacious deck area featuring additional lounge chairs. A grill is positioned nearby, enhancing the outdoor enjoyment.

Home in Sarasota

4.96 out of 5 average rating, 184 reviews

The Palms-Private Heated Pool Hot Tub-5mi to beach

THE PALMS is a single-family home with heated private pool in the heart of Sarasota. The home is 5 miles to the #1 beach in the USA, Siesta Key Beach. It offers 3 bedrooms, 2 bathrooms, a large living space & screened-in outdoor sunroom. The fully private, fully enclosed outdoor space is one-of-a-kind with a modern pool, hot tub, BBQ grill, fire pit, beach bar, outdoor TV & lounge chairs for families & snowbirds to enjoy Florida living in style!

A serene pool area is captured, featuring a turquoise pool surrounded by a screened enclosure. Comfortable lounge chairs are positioned nearby, and a decorative statue is visible by the pool's edge. Lush greenery and a wooden fence enhance the tranquil setting.

Guesthouse in Sarasota

4.99 out of 5 average rating, 140 reviews

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

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Popular amenities for South Sarasota rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

Home in Sarasota

4.97 out of 5 average rating, 69 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

A screened-in patio encloses a private pool, featuring a pink inflatable flamingo in the water. Lounge chairs are positioned around the pool area, and a hanging chair is visible in the corner. Lush greenery surrounds the space, offering a sense of privacy.

Home in Sarasota

4.83 out of 5 average rating, 6 reviews

The Velvet Blue house 3/2+Pool+5 min Siesta Key

An aerial view of a single-story home with a blue exterior and a metal roof highlights a private pool surrounded by a spacious patio. Lush landscaping and palm trees create a tropical atmosphere, while a shaded seating area under the umbrella invites relaxation.

Home in Sarasota

5 out of 5 average rating, 28 reviews

Stunning Home, Heated Pool and Boat Dock

The exterior of the home showcases a one-story structure surrounded by a well-kept lawn. A covered parking area is present, alongside vibrant landscaping featuring various plants and trees. Clear blue skies create a bright and welcoming atmosphere.

Home in Sarasota

4.94 out of 5 average rating, 152 reviews

La Hacienda / heated pool, hot tub, 6 mi to beach

The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.

Home in Sarasota

4.88 out of 5 average rating, 156 reviews

5 minutes to private Siesta Key Beach + 2 pools

Top guest favorite

A screened lanai showcases a heated pool and spa, surrounded by twinkling string lights. Lounger chairs and outdoor dining furniture are positioned nearby. A grassy area is visible beyond the pool, while a pink inflatable floats in the water, enhancing the serene outdoor setting.

Home in Sarasota

4.98 out of 5 average rating, 51 reviews

Charming Home in Sarasota-8min from Siesta Key

Top guest favorite

A private fenced yard features a large swimming pool surrounded by a patio. Two lounge chairs are positioned nearby on a sunlit deck. A covered porch is visible in the background, offering additional seating options. Lush greenery borders the space, enhancing relaxation.

Home in Sarasota

4.89 out of 5 average rating, 79 reviews

Gorgeous renovation with pool, minutes from beach

A lush garden area is highlighted by tropical plants and palm trees, framing a clear view of the private swimming pool. The grassy space features a circular flower bed and outdoor seating, accompanied by the inviting sunlight filtering through the greenery.

Home in Sarasota

4.71 out of 5 average rating, 17 reviews

Cheerful 4-bedroom home with a private pool

Condo rentals with a pool

A community pool area is highlighted, featuring a clear blue pool surrounded by lounge chairs. The yellow building with arched windows stands in the background, and palm trees add greenery to the serene environment. A sunny sky enhances the overall vibrant atmosphere.

Condo in Sarasota

4.97 out of 5 average rating, 201 reviews

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

The image features a sparkling blue pool surrounded by a spacious patio area. Palm trees and lush greenery enhance the scenery, while the nearby Tiki Hut provides shaded seating. The backdrop includes a serene view of the water, with boats visible in the distance under a partly cloudy sky.

Condo in Siesta Key

4.84 out of 5 average rating, 238 reviews

Cozy 1BR Beach Condo on Siesta Key!

Top guest favorite

Condo in Siesta Key

4.97 out of 5 average rating, 320 reviews

On the Beach; Siesta Key SunBum Studio

An inviting pool area is showcased, featuring a crescent-shaped pool with steps leading in. Surrounding lounge chairs are arranged neatly along the pool deck, with palm trees adding greenery to the scene. A small shed is visible in the background, enhancing the tropical ambiance.

Condo in Sarasota

4.91 out of 5 average rating, 116 reviews

Siesta Key - 1/2 Mile to the Beach!

A large heated pool is visible, surrounded by lounge chairs for relaxation. Tall palm trees frame the area, and the building's exterior provides a backdrop. The clear blue water reflects the sunny sky, inviting guests to enjoy a refreshing swim.

Condo in Sarasota

4.86 out of 5 average rating, 149 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

A large heated outdoor pool is surrounded by lounge chairs, offering ample space for relaxation. The pool area is framed by palm trees, with a view of the condominium building and parked cars in the background, creating a welcoming environment.

Condo in Siesta Key

4.94 out of 5 average rating, 109 reviews

Siesta Key Beach Front Condo

The outdoor pool area features clear blue water surrounded by lounge chairs and tropical landscaping. The pool is fenced with a white lattice and is located near multiple residential buildings, offering a relaxed environment for sunbathing and leisure.

Condo in Sarasota

4.92 out of 5 average rating, 143 reviews

Cottage on Siesta Key Your own getaway!

A charming studio space features a queen size bed with a white blanket and decorative pillows. A small nightstand sits beside the bed, and a light is positioned for reading. Natural light enters through a large window with blinds, complementing the wood-look flooring.

Condo in Lido Key

4.96 out of 5 average rating, 140 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

Quick stats about vacation rentals with a pool in South Sarasota

Total rentals
210 properties
Nightly prices starting at
€ 43 before taxes and fees
Total number of reviews
5.7K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
150 properties have a dedicated workspace

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