Holiday 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.

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Guest favourite

Bungalow in Sarasota

4.91 out of 5 average rating, 345 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 favourite

Home in Sarasota

4.95 out of 5 average rating, 486 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!

Top guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 332 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 favourite

Home in Sarasota

4.93 out of 5 average rating, 353 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

- Located in a quiet Sarasota neighborhood minutes from shopping, restaurants, & Siesta Key, this amenity packed home is perfect for families and beach enthusiasts! - Enjoy the heated pool and comfy outdoor furniture in your fenced in backyard where you can bask in the sun swimming and grilling. - Beautifully designed coastal interior w/ new appliances, Smart TVs, and fast WiFi. - Your on-site Superhost is available if needed to assist with making your stay enjoyable and worry free.

Guest favourite

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 favourite

Home in Sarasota

4.92 out of 5 average rating, 98 reviews

Saltwater Pool & Hot Tub-Gas Grill-Bikes-Baby Gate

The House - Sleeps 12 people. -Saltwater heated pool -4 person hot tub -Kid’s toys & accessories, including stroller, carseat, highchair, pack and play, etc… -Bikes! -Stocked kitchen -King beds. Location: - 5 minute walk to downtown, 8 minute drive to Lido Key Beach. -Directly next to our “sister house” … book both for huge groups! Hosts -Small family run side-business. We love connecting with visitors! WE OFFER A DISCOUNT FOR PUBLIC SCHOOL TEACHERS! Message us for info!

Guest favourite

Apartment in Sarasota

4.87 out of 5 average rating, 109 reviews

Anchor house +6 min. from Siesta Beach+heated pool

★ "Ground floor 1 bedroom 1 bathroom apartment" ★ "An incredible apartment and 6 star hospitality!" 🌴 Stylish Retreat Near Siesta Key Heated Pool! Welcome to your perfect Sarasota getaway! This 600 sq. ft. pet-friendly home offers a heated pool access, and a prime location just 6 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.

Guest favourite

Flat in Sarasota

4.96 out of 5 average rating, 136 reviews

Free Early Chk-in, Super Clean, Parking, Disney+.

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 favourite

Guest house 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 favourite

Flat in Sarasota

4.89 out of 5 average rating, 152 reviews

Downtown Apartment w/ Pool, Gym, & Coworking 329

This 2/2 apartment features an oversized kitchen with island, slider with views of Downtown. Primary has a king bed and en-suite bathroom. 2nd bedroom has a twin bed with twin trundle. Shared amenities include: gym; sunset deck; massive roof deck with heated pool; gazebo with big-screen TV, fireplace, wet bar, dog run and access to the adjacent Cowork office space building. Also on-site is a full service cafe.

Guest favourite

Island in Sarasota

4.97 out of 5 average rating, 324 reviews

Now NEW AUG Openings! Sarasota #1 Lux BEACH Villa

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!

Guest favourite

Home in Sarasota

4.95 out of 5 average rating, 208 reviews

2bed/2bath with POOL house, close by SIESTA KEY!!!

By customers requirements from April 1st will be HEATED POOL! Living room has a sectional with pull out full size bed. 1st. bedroom king size bed, 2nd. bedroom queen size bed. House great for families, located within 10-15 mins of siesta key beach #1 beach in US. 10 minutes from Sarasota Downtown. NOTE: We allow ONLY dogs till 30lb. For Extra 150$ fee.