
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.

The Wisteria Oasis W/swings, heated pool & hot tub
A Florida wellness retreat>>> Discover the charm of our delightful cottage, exceptionally placed amidst lush greenery! The interior offers an inviting ambiance with its plush, comfortable furnishings and a well-equipped kitchen with an espresso machine. Quietly nestled away from the hubbub of city life, our cottage offers a tranquil escape yet is in close to local attractions. Relish the day exploring charming seaside villages and beaches or simply bask in the serenity of your private haven.

Private Heated Pool Retreat for Two Families
🌴 Welcome to your private Sarasota escape - designed for easy, extended stays, where two families can relax together around a private heated pool. With generous living spaces and thoughtful touches throughout, the home balances comfort and connection. Located minutes from Siesta Key, Lido Beach, and downtown Sarasota, and within walking distance of a park with playground, public pool, courts, fitness areas, and scenic trails. Relaxed, comfortable, and ideal for memorable family getaways.

Sun-Kissed Memories: Open Sunday Night!
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

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

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. If we are booked check out our additional units under our profile.

Family Friendly w/Free Heated Pool Near Beach
Welcome to Vistalodgings Villa Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀ Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

Luxury Pool Retreat Near Beach & Downtown 3BR/2BA
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!

Heated saltwater pool near Siesta and Downtown
Escape to our brand-new, modern Sarasota home, perfect for families! Enjoy a private heated saltwater pool just steps from the master suite. Located minutes from the world-famous Siesta Key Beach and vibrant downtown Sarasota. This stylish oasis comfortably accommodates up to 10 guests, offering the ultimate Florida retreat with all-new furnishings and a fully equipped kitchen. Your private getaway awaits!

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.

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. 🌴

JULY AVAIL! 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!

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 Sarasota rentals with a pool
House rentals with a pool

The Sand Castle - Backyard Oasis Mins from Siesta!

Private Pool +Game Room Near Siesta Key | Sleeps 9

Luxury Sport Vacation Pool House-Downtown Sarasota

The Blessing House- Htd Pool/Spa, Close to Beaches

Bike to Beach Double King Suites, Pool & Mini Golf

Sarasota Pool Home| Hot-tub| 2-miles to Siesta

Sunshine House- Sarasota Pool Retreat

Sarasota Paradise/Stunning Home/Heated Pool
Condo rentals with a pool

6 Siesta Breakers - Condo, Ocean View, Heated Pool

The Honeymoon Suite on Siesta Key Beach

Comfy Siesta Key Condo

Sunset and beach view from your balcony Unit 403

Heated Pool Apartment Near Siesta Key | 1BR

Beach Front Madeira Beach

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

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

Pickleball, Kayak, LegacyTrail, Beaches, Downtown

Paradise on Prospect w/ Htd Saltwater Pool

The Palms Away

Homey Downtown Studio Apartment

Beach Escape+Downtown | large yard/Heated pool

Stunning New 3 bed 3 bath pool home by Siesta Key!

Private Getaway Near Siesta Key!

New Modern Longboat Key*5 Steps to Sand*Heatd Pool
When is the best time to visit Sarasota?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $309 CAD | $388 CAD | $407 CAD | $310 CAD | $273 CAD | $275 CAD | $273 CAD | $260 CAD | $244 CAD | $250 CAD | $273 CAD | $311 CAD |
| 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 Sarasota

Total vacation rentals
Explore 1,070 vacation rentals in Sarasota

Nightly prices starting at
Sarasota vacation rentals start at $14 CAD per night before taxes and fees

Verified guest reviews
Over 33,690 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 420 rentals that welcome pets

Rentals with dedicated workspaces
730 properties have a dedicated workspace

Wifi availability
1,070 of Sarasota vacation rentals include wifi 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
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