
Vacation rentals with a pool in Sarasota
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Sarasota

Total vacation rentals
Explore 1,100 vacation rentals in Sarasota

Nightly prices starting at
Sarasota vacation rentals start at €9 per night before taxes and fees

Verified guest reviews
Over 36,620 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 410 rentals that welcome pets

Rentals with dedicated workspaces
700 properties have a dedicated workspace

Wi-Fi availability
1,100 of Sarasota vacation rentals include wi-fi access

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

4.9 Average rating
Sarasota stays are highly rated by guests—averaging 4.9 out of 5!

Nearby attractions
Sarasota's top spots, include Bayfront Park, Marie Selby Botanical Gardens, and Sarasota Jungle Gardens
Top-rated rentals with a pool in Sarasota
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Sunshine House, near Downtown, Legacy Trail, Beach
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.

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

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.

Tiki Bar Paradise! Heated Pool & Gaming Oasis!
Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

The Blessing House- Htd Pool/Spa, Close to Beaches
Welcome to The Blessing House, a beautifully curated Sarasota retreat designed for relaxation, comfort, inspiration, and quality time together. Enjoy a heated pool & spa, lush lanai, bright designer interiors, and a peaceful residential setting just 15 minutes from Siesta Key, Lido Key, and downtown Sarasota. Thoughtfully maintained and enjoyed by our family throughout the year, this home is ideal for couples, families, and discerning travelers seeking a restful and memorable getaway.

Modern, Bright Downtown SRQ A-Frame West of Trail
Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

Luxury Pool Family Paradise-Siesta Key Beach/DT
Welcome to your home away from home! This renovated, spacious and bright pool home will immerse you into 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 USA), 10 minutes to downtown including fantastic restaurants and shopping and walking distance to the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake park and The new UTC mall!

Oasis by Siesta Key Beach and Downtown SRQ w/pool
Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

On the Beach; Siesta Key SunBum Studio
Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs.

Luxury 3/3 with Heated Pool, Spa, & Putting Green!
Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

DEC SALE! Sarasota #1 Luxury Villa w/PRIV BEACH!
BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!
Popular amenities for Sarasota rentals with a pool
House rentals with a pool

Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta

Modern 4bd | Heated Pool | Hot Tub + Studio Suite!

Luxury Lido Key Heated Pool & Game Room

The Palms Away

Private Heated Pool Retreat for Two Families

Lido Key House

Sun Coast Oasis-Heated Pool-Pool Table-Arcade

NEW! Renovated Pool Home Mins 2 Siesta Key Beach
Condo rentals with a pool

The Beach Condo #107 Beachfront Full View

LIDO KEY 1 BR/1Bath Heated Pool 16

Siesta Key Oasis with Gulf Views

Comfy Siesta Key Condo

Lake View 1BR Condo | Heated Pool Near Siesta

Beachwalk Townhouse with view of Gulf of Mexico

Island Time: Discounted August & September!

Cottage on Siesta Key Beachside & Stunning sunsets
Other vacation rentals with a pool

Lido Key Beach Bungalow with Private Heated Pool!

The Bahia. Wellness House heated pool, spa, sauna

Family Fun•POOL•Sleep 14•Game•SRQ, Ami &Beaches

True Island Living House/beach/water views

House of Peace oasis,heated pool, pool table, fire

Beautiful Florida Bungalow: 26-VR-000046

Modern Lido Key Cottage Pool & Steps to Beach

Sarasota Pool Home| Hot-tub| 2-miles to Siesta
When is the best time to visit Sarasota?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €209 | €272 | €281 | €221 | €189 | €194 | €173 | €164 | €155 | €158 | €173 | €197 |
| 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 |
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- Anna Maria Island
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- Raymond James Stadium
- Busch Gardens Tampa Bay
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