
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.

Siesta Key, FL - Casa Berano
Quiet, private home on lovely Siesta Key. 1.6 miles from lovely #1 Beach in the country. 1.9 miles to Siesta Key Village. FREE shuttle to village & beach 7 days a week. Private saltwater pool/enclosed lanai. Spacious 3bd/3b. Pets, dogs only, welcome, pls add to your total guest reservation. Open floor plan, large living area. Kitchen opens into living area & 2 dining areas w/ large tables. 2 car gar. brick paved driveway, in home laundry. 6 Guests Max 2 pets Max (dogs only), under 50lbs

Crystal House on Siesta Key Beach
This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

ROYS PLACE Romantic, Private, Paradise!
NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR THREE YEARS. "I LOVE ROYS PLACE!" Words most commonly used by guests in reviews are "quality" "clean" "cute" "sexy" "cool" "safe" . This is a restored 600 sq. ft. one bedroom apartment in an old historic home located in the heart of coveted safe Northwest Sarasota. Offered for you, a romantic boutique apartment with your own private (exclusive to you, not shared) CLOTHING OPTIONAL lanai, outdoor shower and heated pool.

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!

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!

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.

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

Your private retreat near Siesta Key Beach.
Completely Remodeled Private Retreat. COME RELAX, UNWIND, AND MAKE LASTING MEMORIES! From the moment you arrive, you’ll feel the calm, welcoming atmosphere that makes this property stand out. This spacious 3brm 2-bath features an amazing heated pool, a private backyard, and stylish finishes throughout. Whether you’re lounging by the heated pool, enjoying meals in the bright open-concept living space, or exploring the nearby beaches this home is perfect for an unforgettable vacation

Sarasota Surf & Racquet Club Siesta Key Condo
Our newly renovated condo is located on Siesta Key's award winning Crescent Beach. Our unit is has all of the amenities of home for your convenience. The primary bedroom has a king sized bed and its own ensuite with walk-in shower. The second bedroom has 2 double beds and a large closet for all of your belongings. The complex has two heated pools, multiple charcoal grills and just steps away from the unit are 3 tennis courts and 2 pickle ball courts. Restaurants and shopping close by

Spacious Cozy Tropical Retreat!
You will be impressed with the new Kitchen. The spacious master bedroom has been designed with you in mind. King size bed, large walk in closet and private bath. Both bedrooms have brand new laminate flooring! Relax and unwind in the brand new leather reclining sofas and chair with a 65” smart TV in the main livingspace. The villa comes with high speed WIFI internet and premium tv channels to make you feel right at home. Private lanai with a great view.

Charming Sarasota Home with Pool!
Charming 3/2 home with a pool! very safe neighborhood, 8.9 miles to Siesta Beach and 5.5 miles to Lido Beach. 15 minute walk to The quaint little village of Pinecraft and Der Dutchman Restaurant and more restaurants and shops. Very clean, private back yard, heated pool, coffee station... really everything you need for a relaxing and enjoyable stay in Sarasota.

Rhodes Retreat - Beautiful Pool and Backyard Space
Bright and newly renovated home for a delightful family escape in Sarasota. Central location near beaches, shopping, and downtown, yet nestled in a serene neighborhood. Short walk to charming Amish Village of Pinecraft. Ample parking, garage, and spacious front yard. Option to book separate secondary unit. Siesta Beach 8.7mi, Lido 5.8mi. VR24-00264
Popular amenities for South Sarasota rentals with a pool
House rentals with a pool

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

Gulf Gate Pool Home

Luxury Sport Vacation Pool House-Downtown Sarasota

Beaches, Shopping, Sculling-Sarasota is calling!

The Sea is Calling

Private Siesta Beach House Oasis with Heated Pool.

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

Upscale. Heated Pool. Minutes to the Beach !
Condo rentals with a pool

Sunny 2nd-Floor Condo w/ Heated Pool | 1BR

Siesta Key Beach Gem—Pool | Private Beach | Fast W

On the Beach; Siesta Key SunBum Studio

LIDO KEY 1 BR/1Bath Heated Pool 16

Gateway Siesta Key Beach

5209A Calle Menorca - Siesta Key Village Condo

Sunset and beach view from your balcony Unit 403

Sun-Kissed Memories!
Other vacation rentals with a pool

Endless Summer | Private Pool & HOT TUB

Coastal Calm - 3BD/2BA Heated Pool Near Beaches

Modern Siesta Key Condo 3 minute walk to beach!

New! Siesta Beach Guest House with pool!

Homey Downtown Studio Apartment

*Seaglass Suite at Siesta Shores. Sleeps 2.*

Lanai w/ Pool Views • Minutes to Siesta Key

Cozy 1BR w/ Pool · 4 min from Siesta
When is the best time to visit South Sarasota?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ742 | ﺩ.ﺇ1,102 | ﺩ.ﺇ1,102 | ﺩ.ﺇ914 | ﺩ.ﺇ668 | ﺩ.ﺇ727 | ﺩ.ﺇ720 | ﺩ.ﺇ657 | ﺩ.ﺇ635 | ﺩ.ﺇ646 | ﺩ.ﺇ720 | ﺩ.ﺇ779 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about vacation rentals with a pool in South Sarasota

Total vacation rentals
Explore 280 vacation rentals in South Sarasota

Nightly prices starting at
South Sarasota vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 6,420 verified reviews to help you choose

Family-friendly vacation rentals
240 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
200 properties have a dedicated workspace

Wi-Fi availability
280 of South Sarasota vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across South Sarasota rentals

4.8 Average rating
South Sarasota stays are highly rated by guests—averaging 4.8 out of 5!
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Raymond James Stadium
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- Vinoy Park
- Caspersen Beach
- Lido Key Beach
- Amalie Arena
- Cortez Beach
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- Manasota Key Beach
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