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Vacation rentals with a pool in Sarasota

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sarasota

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

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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, 359 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 private backyard is highlighted by a welcoming pool surrounded by well-maintained pavers. Two yellow lounge chairs are positioned nearby, and a vibrant patterned towel is draped over a lounger. The screened porch provides additional space for relaxation, with a fenced area visible in the background.

Home in Sarasota

4.97 out of 5 average rating, 120 reviews

Sunshine House, close to Downtown

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.

A private heated pool is enclosed by a screened lanai, surrounded by lush tropical plants. Soft purple lights create a relaxed ambiance. Comfortable seating and dining areas are positioned nearby, inviting leisurely moments by the water.

Home in Indian Beach-Sapphire Shores

4.97 out of 5 average rating, 154 reviews

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

Top guest favorite

A private pool area is surrounded by lush greenery, featuring a clear blue water pool and four lounge chairs positioned for relaxation. Umbrellas provide shade, enhancing the serene outdoor space. Tropical plants are situated along the edge, adding to the natural atmosphere.

Home in Sarasota

4.98 out of 5 average rating, 109 reviews

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

Your "Beach Home" w/ heated pool is a private home 1 and 1/4 mile drive to Beach Access 12 on Siesta Key. 3bedroom/2bathroom. It's ideal for families/couples. Everything you need for a great vacation!Fully equip kitchen,towels/linen, laundry room . Large pool w/ gas bbq & patio area. Use our chairs, cooler,umbrella,beach cart.STRICT OCCUPANCY OF MAX 6 PEOPLE INCLUDING INFANTS/KIDS AT HOUSE. NO OUTSIDE GUESTS DAY/NIGHT. DO NOT BOOK IF YOUR GROUP IS LARGER. No Pets. Min Age 26 to book

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, 504 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

4.99 out of 5 average rating, 223 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

A private pool area is surrounded by a screened enclosure, featuring turquoise water and a white pool deck. Comfortable seating arrangements are placed nearby, along with potted plants that enhance the serene environment. The space is well-lit by natural sunlight filtering through the enclosure.

Home in Sarasota

4.81 out of 5 average rating, 156 reviews

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.

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, 129 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.

Top guest favorite

A private courtyard featuring a heated pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned beside the pool, and a small fountain adds a soothing element. A cozy seating area is visible near the entrance to the adjoining building.

Home in Indian Beach-Sapphire Shores

4.94 out of 5 average rating, 125 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

A private backyard space is depicted, featuring a small, unheated chlorine pool surrounded by lush greenery. Several palm trees and shrubs frame the area, while a seating option is visible beside the pool. A home can be seen in the background, set against a bright blue sky.

Home in Sarasota

4.95 out of 5 average rating, 110 reviews

Rita Retreat - Beautiful 2/2 with private pool

Welcome to your dream vacation home! This charming rental offers a private pool and a lush green area for relaxation and fun. Situated just 4.6 miles away from the stunning Siesta Key beach, you'll have easy access to sun-kissed sands and sparkling waters. Seafood lovers will be delighted to find the renowned Phillippi Creek Oyster Bar nearby, offering some of the best seafood in town. Embrace the Florida lifestyle and make cherished memories in this wonderful retreat!

Top guest favorite

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, 141 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!

A single-story home is depicted, featuring a light-colored facade and a two-car garage. Lush green grass surrounds the property, with palm trees partially framing the view. The sky is filled with fluffy clouds, enhancing the welcoming appearance of the residence.

Home in Sarasota

4.86 out of 5 average rating, 170 reviews

The Sea is Calling

Our home, The Sea is Calling, is located on a cul de sac in Whitfield Estates. It is a short drive to many world class beaches and attractions like Lido Beach, Siesta Key, Longboat Key, Mote Marine, Ringling Museum and Sarasota Jungle Gardens. Our home is welcoming and we hope you decide to let us share a bit of paradise with you. When The Sea is Calling, you must go! We hope to see you soon.

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Popular amenities for 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, 77 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Top guest favorite

Home in Sarasota

5 out of 5 average rating, 66 reviews

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

The heated pool features a distinctive shape with a textured surface and blue tile accents. Lounge chairs are positioned nearby for relaxation, surrounded by lush greenery and colorful plants. The fully fenced backyard offers privacy, creating a tranquil outdoor retreat.

Home in Sarasota

4.96 out of 5 average rating, 214 reviews

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

Top guest favorite

An inviting outdoor lanai is shown, featuring comfortable seating with colorful cushions. A wooden coffee table holds glassware, while a heated pool glistens in the background, surrounded by lush greenery. The screened area offers a seamless connection to the tranquil outdoor environment.

Home in Bradenton

5 out of 5 average rating, 85 reviews

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!

Top guest favorite

An expansive outdoor space features a heated pool and an 8x8 spa, surrounded by a stone patio. Lounge chairs and a patio dining set are arranged invitingly. The sky is painted with soft hues of orange and pink as twilight descends.

Home in Sarasota

5 out of 5 average rating, 46 reviews

Sarasota Memories For a Lifetime

Top guest favorite

An aerial view captures a light blue house with a spacious driveway and manicured lawn, surrounded by lush greenery and a serene canal. The home features a charming front porch and is set within a quiet neighborhood, showcasing the tranquil natural landscape.

Home in Port Charlotte

4.92 out of 5 average rating, 24 reviews

Peaceful waterfront home

Top guest favorite

A private backyard space features a stone-paved area surrounded by lush greenery and landscaping. Two outdoor chairs are positioned adjacent to a small stone table, complemented by terracotta planters. A birdbath adds a charming focal point amidst the serene environment.

Home in Sarasota

4.98 out of 5 average rating, 137 reviews

Take a Siesta off Bahia Vista

The screened lanai features a refreshing private pool, surrounded by a spacious deck. Comfortable lounge chairs adorned with vibrant cushions are positioned beside the water. Lush greenery is visible beyond the pool area, creating a serene retreat for relaxation.

Home in Sarasota

5 out of 5 average rating, 13 reviews

Resort-Style amenities. 2 KING beds. Beach 12 min.

Condo rentals with a pool

Top guest favorite

Condo in Siesta Key

4.97 out of 5 average rating, 331 reviews

On the Beach; Siesta Key SunBum Studio

Top guest favorite

Condo in Bradenton

4.96 out of 5 average rating, 111 reviews

A&A's Paradise near IMG & Anna Maria beaches

A clear heated pool is seen with shimmering blue water, accompanied by several lounge chairs positioned around the poolside. The area is landscaped with greenery, and a shaded pavilion is observable in the background.

Condo in Longboat Key

4.87 out of 5 average rating, 110 reviews

Sunset and beach view from your balcony Unit 403

Condo in Longboat Key

4.91 out of 5 average rating, 181 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

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, 113 reviews

Siesta Key Beach Front Condo

Top guest favorite

A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.

Condo in Longboat Key

4.98 out of 5 average rating, 196 reviews

Condo with View 1: Open Sun - Wed, 10% Off!

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

4.95 out of 5 average rating, 143 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

Top guest favorite

Condo in Siesta Key

4.97 out of 5 average rating, 125 reviews

Siesta Key Condo. Checkout our great rates!

Other vacation rentals with a pool

An inviting outdoor space features a heated saltwater pool surrounded by paver stones. Lounge chairs are positioned along the poolside, with lush greenery and tropical plants enhancing the landscape. A pergola provides shaded seating, creating a comfortable area for relaxation and entertainment.

Home in Sarasota

4.93 out of 5 average rating, 97 reviews

Sea Esta | Private Saltwater POOL + Putting Green!

A private screened-in pool area features a rectangular pool with an attached hot tub. Surrounding the pool, four lounge chairs in bright colors provide options for relaxation, while tropical plants fill the background, enhancing the enclosed atmosphere.

Home in Longboat Key

4.89 out of 5 average rating, 9 reviews

Beautiful Island Beach House

Top guest favorite

A large, inviting pool is surrounded by lush greenery and tall pine trees. Several lounge chairs are visible around the pool area, with bright sunlight reflecting off the clear water. The depth marker indicates a shallow end of 3 feet 6 inches.

Villa in Sarasota

5 out of 5 average rating, 33 reviews

Vacation Villa/Resort Pool 4 miles to Siesta Key

Top guest favorite

An inviting outdoor space features a private heated pool surrounded by tropical plants and palm trees. Comfortable lounge chairs are positioned by the poolside. String lights provide a soft glow against a backdrop of colorful evening skies, while a shaded seating area offers a place to relax.

Home in Sarasota

5 out of 5 average rating, 7 reviews

Luxe Lido Key Escape with Private Pool

Home in Bradenton

4.91 out of 5 average rating, 11 reviews

Sunny Florida River Strand Golf & Resort Vacation

Top guest favorite

A dining area is presented with a large wooden table surrounded by blue upholstered chairs. Sunlight pours through expansive windows, revealing views of the turquoise waters and sandy beach beyond. A beach-inspired artwork decorates the wall, adding a touch of coastal charm.

Condo in Sarasota

5 out of 5 average rating, 55 reviews

Breathtaking Beachfront Views in Siesta Key

Top guest favorite

A spacious pool area is depicted, featuring clear blue water surrounded by a large stone patio. Colorful umbrellas provide shade, while lounge chairs and green Adirondack chairs are positioned for relaxation. Lush tropical plants frame the scene, enhancing the inviting poolside atmosphere.

Apartment in Sarasota

5 out of 5 average rating, 60 reviews

Graceful Getaway Studio

Top guest favorite

The image showcases a vibrant backyard area featuring a heated swimming pool under a screened enclosure. Comfortable seating is arranged, and a private mini golf course is visible. A separate game room with entertaining equipment like shuffleboard and a colorful mural is also displayed.

Home in Bradenton

5 out of 5 average rating, 29 reviews

FREE Heated Pool•Mini Golf•Arcade•Spa•AMI 6mi•IMG

Quick stats about vacation rentals with a pool in Sarasota

Total rentals
1K properties
Nightly prices starting at
ﺩ.ﺇ37 before taxes and fees
Total number of reviews
29K reviews
Family-friendly rentals
800 properties are a good fit for families
Pet-friendly rentals
380 properties allow pets
Rentals with dedicated workspaces
610 properties have a dedicated workspace

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