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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Guest favorite

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, 348 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.

Guest favorite

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, 490 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!

Guest favorite

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, 131 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, 335 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!

Guest favorite

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.

Guest favorite

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

Guest favorite

A serene pool area is surrounded by lush greenery and wooden fencing. Aquamarine water reflects sunlight, while a few poolside lounge chairs in turquoise invite relaxation. Potted plants add a touch of color, and a floating pool accessory rests on the surface.

Home in Sarasota

4.93 out of 5 average rating, 105 reviews

5Stars Tiki, Heated Pool, Close to Beaches and ALL

Beautiful home with amazing pool and landscape, 15 minutes from Siesta Key Beach, 25 minutes from Lido Key Beach and Venice Beach. Close to grocery stores, parks, biking trails, shopping and restaurants. Enjoy the pool, entertain your family in our tiki bar, meditate in our amazing backyard or rest in our tastefully decorated bedrooms. Two pets under 30 pounds are allowed. Our pet fee is $150/dog. Please enter your pet when you complete the reservation.

Guest favorite

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, 183 reviews

The Palms-Heated Private 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 and snowbirds to enjoy Florida living in style!

Guest favorite

A spacious backyard is shown at sunset, featuring a heated pool surrounded by a tiled patio. Tropical palm trees frame the area, and a tiki bar can be seen in the background. Soft outdoor lights create a welcoming ambiance as the sky fills with vibrant orange and purple hues.

Home in Sarasota

4.95 out of 5 average rating, 130 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ask for!

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, 139 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!

Guest favorite

Apartment in Sarasota

4.89 out of 5 average rating, 283 reviews

VILLA 3 · Pool view. Walk to beach. Daily rentals

Villa 3 is newly renovated Everything has been remolded and upgraded Featuring 1 bedroom, 1 bathroom,With 2 person shower with beach pebble floor Separate living room, With Large SMART TV A/C, stainless steel fridge, freezer, toaster, free wifi 2 minutes walk from your door to the beach access #13 Shared swimming pool at your door Perfect for couples No smoking No pets Great Location Good Value

Guest favorite

A screened-in pool area features a sparkling pool with loungers nearby. A dining table sits under a covered area, surrounded by tropical plants and lush greenery. Soft lighting fixtures hang above, creating a serene atmosphere for relaxation.

Guest suite in Sarasota

4.94 out of 5 average rating, 213 reviews

Sunshine Inn Paradise

Sunshine Inn Paradise Come as guests, stay as friends, leave as family! Step into your private oasis with a sparkling pool, outdoor shower, and deck surrounded by lush gardens. Whether you’re here to relax or explore, everything you need is here We don’t just offer a place to stay—we offer a place to belong. We can’t wait to welcome you as a guest and see you off as family.