
Vacation rentals with a pool in Sarasota County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Sarasota County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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
ValueFamilyTV
4.89 out of 5 average rating, 107 reviews
Pool & fenced-in yard in downtown edge bungalow
MESSAGE ME FOR DAYS U DONT C. This 2 bed-2 bath house is an original Florida bungalow with wood floors & natural light in quiet neighborhood on downtown core edge. Spacious, private fenced-in backyard with pool, covered grill and eating area. Minutes away from Siesta and Lido beaches, the Legacy Trail, Bay and Payne parks, dining, live music, bars, theatres, comedy, opera, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping & more.
LocationFamilyHospitality
4.92 out of 5 average rating, 385 reviews
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
LocationValueParks
4.91 out of 5 average rating, 140 reviews
Heated Pool Oasis 3BR/2BA near Siesta Key Beach
Relax at this modern heated pool house located just 15 min from the famous Siesta Key Beach. Nested in a quiet neighborhood with a lot of privacy, the house has plenty of space for an entire family or a group of friends. An additional family room with a TV for kids. Relax by the pool in the spacious outdoor area or explore the beautiful downtown filled with restaurants. Recently renovated, this home offers handmade authentic Mexican tile flooring to compliment a cozy and contemporary design.
LocationFamilyCleanliness
4.98 out of 5 average rating, 162 reviews
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!
ValueFamilyAccuracy
4.96 out of 5 average rating, 154 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.
ValueLocationHospitality
4.8 out of 5 average rating, 189 reviews
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
ValueFamilyAir conditioning
4.88 out of 5 average rating, 103 reviews
Graceful Getaway
Welcome to our Graceful Getaway Poolside Studio nestled in the heart of sunny Sarasota! We have a beautiful pool, hot tub, and lounge area.(Shared pool) This cozy retreat offers comfort and convenience for couples or solo travelers seeking a relaxing getaway. You will be greeted by a bright and airy space with cheerful decor and vibrant accents! The open floor plan creates a sense of spaciousness, while large windows flood the room with natural light, providing an inviting atmosphere!
FamilyValueCheck-in
4.98 out of 5 average rating, 116 reviews
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.
ValueFamilyView
4.93 out of 5 average rating, 409 reviews
~Flamingo House~3 br,3 bath, heated pool~
Welcome to The Flamingo House with beautiful private pool area surrounded by privacy fence and palms. Take a short drive to beautiful Downtown Sarasota or Marina Jack for the sunset. Plus Legacy Trail is accessible from our street w/Pompano Pickleball court close by. Ice cream, coffee shops and restaurants are within 5 minutes. Situated on a quiet street while still being close to main roads, and an easy 20 minutes to Siesta Key and Lido Key beaches,5 minutes to Pinecraft.
FamilyLocationAir conditioning
4.85 out of 5 average rating, 221 reviews
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!
LocationValueComfort
4.92 out of 5 average rating, 172 reviews
The Oasis-Private Heated Pool Hot Tub-5mi to beach
"The Oasis" is a renovated beach cottage with heated private pool & hot tub in the heart of Sarasota. It's 5 miles to the #1 beach in the USA: Siesta Key Beach. The cottage offers 2 bedroom & 2 bathrooms, and a bonus room that can be used to sleep 6 comfortably. The one-of-a-kind fully private, fully enclosed backyard includes heated pool, hot tub, BBQ grill, outdoor dining table & fire pit for families & snowbirds to enjoy Florida living!
LocationFamilyBiking
4.96 out of 5 average rating, 227 reviewsPopular amenities for Sarasota County rentals with a pool
House rentals with a pool

Tiki Bar Paradise! Heated Pool & Gaming Oasis!
LocationValueNearby
4.94 out of 5 average rating, 106 reviews
Luxury 3/3 with Heated Pool, Spa, & Putting Green!
FamilyLocationBeach
5.0 out of 5 average rating, 110 reviews
The Oasis
LocationFamilyHospitality
4.98 out of 5 average rating, 129 reviews
Oasis by Siesta Key Beach and Downtown SRQ w/pool
FamilyLocationBackyard
4.94 out of 5 average rating, 143 reviews
Lakefront Getaway in Sunny FL
ValueFamilyIndoor spaces
4.9 out of 5 average rating, 101 reviews
St Armand's Mid-Century Oasis
ValueLocationTV
4.9 out of 5 average rating, 163 reviews
Sarasota Getaway “Have some fun under the sun.”
LocationValueQuiet
4.85 out of 5 average rating, 133 reviews
3 bedroom Heated salt water pool close to Siesta
LocationFamilyLaundry
4.97 out of 5 average rating, 119 reviewsCondo rentals with a pool

Heated Pool Apartment Near Siesta Key | 1BR
LocationFamilyAmenities
4.87 out of 5 average rating, 157 reviews
LIDO KEY 1 BR/1Bath Heated Pool 16
LocationFamilyCheckout
4.82 out of 5 average rating, 154 reviews
Gateway to Siesta Key - 1/2 Mile to the Beach
FamilyLocationView
4.96 out of 5 average rating, 225 reviews
Modern Coastal Oasis - Beach and Private Patio
LocationValueBeach
4.96 out of 5 average rating, 164 reviews
Luxury King Suite just steps to Siesta Key Beach
LocationValueHospitality
4.87 out of 5 average rating, 181 reviews
5213A Calle Menorca - Siesta Key Village Condo
LocationValueComfort
4.86 out of 5 average rating, 129 reviews
Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool
LocationFamilyAir conditioning
5.0 out of 5 average rating, 109 reviews
LJ's Cottage 2
FamilyValueIndoor spaces
4.83 out of 5 average rating, 115 reviewsOther vacation rentals with a pool

Private Siesta Beach House Oasis with Heated Pool.
LocationFamilyNearby
4.85 out of 5 average rating, 320 reviews
Quiet Family Home w/ Pool Near Pinecraft
LocationFamilyPool
4.93 out of 5 average rating, 43 reviews
Siesta Key-Private Family Pool Home-6 min to Beach
LocationFamilyBathroom
4.83 out of 5 average rating, 63 reviews
Sleeps 8, Private Pool Near Siesta Key
FamilyLocationLayout
4.96 out of 5 average rating, 48 reviews
Good Vibrations Home
FamilyLocationQuiet
5.0 out of 5 average rating, 18 reviews
GARDEN VIEW HOUSE WITH A POOL
FamilyValuePool
4.98 out of 5 average rating, 96 reviews
Paradise Villa- Sarasota
FamilyLocationLaundry
4.8 out of 5 average rating, 100 reviews
Bee Keepers Cottage
LocationFamilyComfort
4.97 out of 5 average rating, 75 reviewsDestinations to explore
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- Anna Maria Island
- Siesta Beach
- Captiva Island
- Anna Maria Island Beach
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Caspersen Beach
- Vinoy Park
- Manasota Key Beach
- John's Pass
- Tropicana Field
- Englewood Beach
- Crescent Beach
- Img Academy
- Anna Maria Public Beach
- River Strand Golf and Country Club
- Cortez Beach
- Fort De Soto Park
- North Beach At Fort DeSoto Park
- Myakka River State Park
- Lido Beach
- Stump Pass Beach State Park
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