
Vacation rentals with a pool in Sarasota Beach
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Top-rated rentals with a pool in Sarasota Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Sarasota Beach rentals with a pool
House rentals with a pool

Sun-filled cottage with pool, walk to beach
We loved staying here! The house was very clean and we felt right at home! We absolutely LOVED the backyard area with the private pool! The location was very walkable! The owner’s were very responsive and kind!

Retreat by the Bay-Heated Saltwater Pool
Will's place was amazing! Super clean, comfortable, and exactly as described. The location was perfect - there was so much to do nearby, from the beach, great restaurants and shops. Will was also a fantastic host: responsive and helpful. Highly recommend staying here if you're looking for a spot that's both relaxing and close to all the action!

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.

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!

Oasis by Siesta Key Beach and Downtown SRQ w/pool
We had the best stay in Sarasota and didn’t want our trip to end! The house was beautiful and in a great location, close to shops, restaurants and not too far from the beach! Michael’s place was very accommodating and has all the amenities. Michael was very responsive and helpful. Loved having access to all the beach chairs and towels. We will for sure be back!!

Charming Home in Sarasota-8min from Siesta Key
The hosts were very responsive and very helpful. Their home was spotless. The pool with the enclosure allowed you all the sunshine you could ask for without the bugs! The interior is very spacious and great for hosting dinner. With the turf back yard it’s the perfect hangout for adults and children! The hosts are very thoughtful with items available for the perfect beach day (beach wagon, chairs, a cooler, and lots of fun items for children! We will definitely be visiting again!
Condo rentals with a pool

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 absolutely loved the space—beautiful, clean, and cozy. The spot by the pool is amazing, and you can’t beat the quick walk to the beach. Everything was perfect for a relaxing getaway. We’ll definitely be back!

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.

LIDO KEY 1 BR/1Bath Heated Pool 16
Had a great stay and everything was as listed. Clean and convient, quiet location, 5 minute walk to the beach. Was located right across from both pool and laundry room (quarters only) which was great. William also provided beach chairs and umbrella as well as small cooler which was exactly what I needed

Siesta Key Ground Floor Condo 2BR On Trolley Line
Great stay, the location, the amenities all were wonderful. Melissa and Brandon were super responsive and the place had more essential stocked than most of the other places we have stayed, which was very thoughtful. Melissa also had a regular coffee pot sent out to us right away, since we don’t use Keurig’s which was super nice and very much appreciated. We would definitely come back!

Perfect Location in Siesta Key
Rick’s place is in an unbeatable location a 2-minute walk from the center of Siesta Key Village and a 5-minute walk from the beach. But it’s also quiet and private, with great indoor space, a deck, and even a decent sized private yard. The condo has high ceilings, laundry, and tons of towels — I’m glad I didn’t pack my beach towels! It also has parking and a small shared pool. This is definitely where you want to stay!

Cottage on Siesta Key Your own getaway!
Julie was a fantastic host. Responded to all questions in a very timely manner. She went above and beyond to make sure my girls group had a good time! Trolley service is at the curb to take you to the village or elsewhere. Restaurants are right across the street for breakfast, lunch, and dinner, so no cooking was needed for us! Thank you for a great experience.
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
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- 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