
Holiday rentals with a pool in Sarasota Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Sarasota Beach
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Sarasota Beach rentals with a pool
House rentals with a pool

Ground floor home 2BD2BA garage Pool Private beach
We had a fabulous stay! The location is perfect. The condo was spotless and nicely decorated. We had absolutely everything we needed. The private beach was clean and not crowded. Chairs were readily available. The location is great. There was an unexpected issue when we first arrived, but Amy was incredibly responsive and supportive, checking in regularly to make sure we were okay and comfortable. Her excellent communication and customer service was exceptional. Once everything was settled, we were able to fully enjoy the space and the beautiful surroundings. Can't wait to go back. We would definitely recommend booking this property.

Pool, Spa, & Private Gym in the Heart of Sarasota
We had a great stay at the house. Loved the interior decor. Looks like the home was remodeled recently. Everything was fresh and clean. We loved hanging out by the pool. Backyard was very private and peaceful. Posts were very quick with their responses if I had any questions about the home. We would definitely stay at the Home again when we’re in town.

Paradise on Prospect w/ Htd Saltwater Pool
This is the nicest vacation rental. The details are spot on. It is well appointed with quality products. PMI Is very responsive. Love the location and proximity to Ed Smith, Downtown Sarasota and more. We look forward to returning.

Stunning Home, Heated Pool and Boat Dock
We had an amazing week at this beautiful home just 10 minutes from Siesta Key. The house was spotless, super comfortable, and had everything we needed; the pool, boat dock, games, comfy beds, and a great TV setup. Everything was perfect. Jennifer was an amazing host as well; very responsive, respectful, and friendly. You can tell she puts a lot of care into keeping the place clean and welcoming. Definitely recommend!

New remodel- 150 Yds to Beach and Restaurants!
We enjoyed our stay! Very clean and has everything you’d need. John is very responsive which we appreciated. Would recommend staying here!!

La Hacienda / heated pool, hot tub, 6 mi to beach
Fantastic Airbnb! Seaglass Management and Joy are great to work with. Very responsive! Great location, very safe, amazing pool and jacuzzi, close to downtown, restaurants and the Legacy bike trail. Will definitely book again in the near future.

2bed/2bath with POOL house, close by SIESTA KEY!!!
We absolutely loved our stay here! The house is beautiful and has everything we needed for vacation. The pool was perfect for the kids - they preferred staying home at the pool than going the beach. Romulda was also so helpful and responsive to all our questions. We only wished we had more time to stay here! We’re looking forward to booking again in the future!

☀Coastal Gem☀Heated pool & amazing location!☀
This is a beautiful, peacefull, prívate and clean place to stay. Natalie is very Nice, we had a wonderfull time, we definitely recomment this place without a doubt, we were delighted
Condo rentals with a pool

Best Siesta Key Condo
We had a very good time at Siesta Key and enjoyed our time at Maureen's place. The building is older, the amenities are well maintained and the condo itself is well cared for. I did find some mystery stains on the mattress and the decorative pillows in my room, but I'm guessing they are just spills that were difficult to get out. More importantly, the boat dock is usable, albeit with some difficulty if the boat is larger than 22 feet or so. We figured out on the second day that the best way to dock was parallel to the intracoastal between the posts and to tie off with lines on either side of the stern and with a single line on the bow. I would check ahead to make sure the dock is available, but we had no other boats docked there on a holiday weekend. The private beach access was a lifesaver on a holiday weekend, despite the short walk required to get there. Having both intracoastal and beach access is the biggest value of the place in my opinion.

Beautiful White Sand Siesta Key Beach
my wife and I spent a wonderful week at Connies place , great location to the pool and beach, the unit was SPOTLESS, well equipped with anything you would need , parking spot right outside our door was great , comfy bed, really nice sand chairs for the beach, always got quick answers to any questions ( none problem related) would highly recommend for any couple looking for a perfect getaway, hoping Connie and her family are well

Cozy 1BR Beach Condo on Siesta Key!
We had a wonderful time at Bill's place, very cozy and had everything we needed. Loved being able to walk to the beach and spent some time at the pool, we had so many more things we wanted to do and not enough time in the day!

Sea Club 2-Relaxing Siesta Key Condo-Siesta Sky
Absolutely love Sea Club. This was our second stay there. Will always come back. Walk to the beach is not bad at all. Condo is next to the road but still quiet. Really enjoyed our stay!

2 Bed/2 Bath Condo Resort View on Siesta Key Beach
The location was great, close to village as well as crescent beach. Lots of restaurants, bars, and excursions close by. Private beach which is wonderful, they offer umbrella rentals for a very reasonable price. Two pools which allowed for plenty of space as neither pool was crowded. The condo came with adequate linen/towels with an exchange halfway through the week which was great. There were extra beach toys, umbrellas, and a cooler in the closet we found a few days in that came in handy.

Crystal House on Siesta Key Beach
Our stay with Eric was amazing! We needed a quick beach weekend and this exceeded our expectations. His unit was as described with luxury towels and bed linens. Beach closet was bonus…the cart, cooler and chairs was much needed and appreciated! I messaged Eric prior to our arrival asking if there was a volleyball in the closet so I could add to our grocery order if not. First thing I saw as we walked in the unit was a new volleyball sitting on the table awaiting our arrival! Way above and beyond! Easy check in and check out. Actually, our flight was ahead of schedule and Eric allowed us early entry to get our trip started a bit sooner! This was our first time visiting the area and definitely plan on returning and will stay here again. Thanks for a great stay!

Deluxe 2/2 Pool View, terraces, Top Floor
Stayed for the month and didn’t want to leave! Great location, very clean and beautifully decorated! Clara was very responsive, to the point where she went out of her way to find extra, personal beach chairs when we needed them! I can’t say enough positive comments about our experience.

A Hidden Gem in Paradise
Diana’s place is a very comfortable. Very clean, cozy, with a fully equipped kitchen, stove, dishwasher, large refrigerator, washer and dryer. There is a private barbecue area and a reserved parking space. 10 minutes by car to Siesta Beach and 13 minutes to Turtle Beach. We found a beach umbrella and chairs in the apartment’s closet. Also there is a safe in the bedroom which made us feel protected. We are definitely very happy that we stayed at Diana’s place and can recommend it to anyone who wants to come to Sarasota for the holidays.
Home rentals with a private pool

New! Beautiful Pool Home Near Siesta Key Beach
It was a short stay for us, but it was exactly what we needed! The house was fully stocked with necessities. Instructions were very clear, not overwhelming. The neighborhood is nice, very close to supermarkets, shopping, restaurants, coffe shops, beach, and local areas whether you want a casual night out or a party night out! Great location😉

Sunny Palmetto Oasis: 4br Home with Private Pool
Thank you RedAwning Rental for the stay in Palmetto!

New! Poolside Sunset Serenity In South Gulf Cove

Comfy Home W/ Heated Pool Near Siesta Key Beach
Destinations to explore
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Seminole Holiday rentals
- Tampa Holiday rentals
- Central Florida Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Holiday rentals
- House rentals Sarasota Beach
- Pet-friendly rentals Sarasota Beach
- Family-friendly rentals Sarasota Beach
- Rentals with breakfast Sarasota Beach
- Apartment rentals Sarasota Beach
- Waterfront rentals Sarasota Beach
- Rentals with an EV charger Sarasota Beach
- Rentals with a patio Sarasota Beach
- Rentals with a kayak Sarasota Beach
- Rentals with outdoor seating Sarasota Beach
- Rentals with a hot tub Sarasota Beach
- Beach house rentals Sarasota Beach
- Cottage rentals Sarasota Beach
- Rentals with a fire pit Sarasota Beach
- Fitness-friendly rentals Sarasota Beach
- Beachfront rentals Sarasota Beach
- Kid-friendly rentals Sarasota Beach
- Rentals with a washing machine and dryer Sarasota Beach
- Luxury rentals Sarasota Beach
- Townhouse rentals Sarasota Beach
- Rentals with beach access Sarasota Beach
- Condo rentals Sarasota Beach
- Rentals with a fireplace Sarasota Beach
- Rentals with pools Siesta Key
- Rentals with pools Sarasota County
- Rentals with pools Florida
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- River Strand Golf and Country Club