
Vacation rentals with a pool in Sarasota County
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Top-rated rentals with a pool in Sarasota County
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Popular amenities for Sarasota County rentals with a pool
House rentals with a pool

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!

Deja Blue Villa Salt Water Heated Pool & Spa
My family and I stayed here for a week as we made our first visit to the area. The house had everything we could’ve needed for us and our kids (5&2) to comfortably stay. Everything was clean when we arrived. The pool was a favorite for us and our kids. The location of the house was great- easy drive to beaches, restaurants and shopping. Vincent was a responsive host and we had no issues with our stay. Would stay here again for sure!

Spacious 2 Bedroom Home | Near Beach | Heated Pool
The stay was in a nice neighborhood. Enjoyed spending time at the pool there. The house was clean and free of clutter. When we had issues with the AC, Melissa responded right away and worked hard to fix the issue immediately. She refunded us the night as we stayed at a hotel with the house at 80. The AC got fixed the next day and we stayed our final night. Thanks Melissa for all your help making for a great stay.

Morning Side
Morningside was in a great location, very clean and well furnished. John was very responsive. Beautiful pond in the back with lots of wildlife to see. Very relaxing. The weather was our only issue. It was a risk taken at the start of hurricane season. Therefore we spent quite a bit of time at the house. It was a wonderful stay. Highly recommend.

Lagoon View*Close to Siesta Key*Centrally Located
Loved our stay!! Only comment is that one bathroom only had 4 rolls of toilet paper for 9 people, which wasn’t enough but besides that, we had everything we needed! - Excess towels, sunscreen, games, stocked kitchen with dishes and some snacks. Pool is clean and 3-5 feet. Pool noodles, wagon and cooler available for use which was awesome to borrow 👏🏼

House of Peace oasis,heated pool, pool table, fire
We had an amazing stay! The house was cozy, spacious, and had everything we needed. We loved the pool and how close it was to Siesta Key—only about 15 minutes, which was perfect since our friends were staying there. The location was great, and the amenities made it feel like home. Stephanie was such a friendly and helpful host. We'd definitely stay here again!

New pool 3br 3b #1 Ranked Siesta Key w Game Room
Steve was the perfect host as always, super responsive and made for a smooth and peaceful stay. Check-in and check-out was a breeze, highly recommend and will stay again!

Coastal Pool Bungalow - 15 Mins to Famous Beaches
We had a great time and everything was perfect! The place was clean, comfortable, and exactly as described. The host was friendly and responsive, which made our stay even better. Would definitely recommend and stay again!
Condo rentals with a pool

Gateway to Siesta Key - 1/2 Mile to the Beach
Excellent place, unbeatable location, very cozy and comfortable. Chris let us know we could check in early without even asking. I would gladly come back!

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!

On the Beach; Siesta Key SunBum Studio
This is our 5th time staying here, and the place and location speak for itself. The one thing that takes this place over the top in our opinion is the amazing and friendly hosts, Honestly they have treated us like family and made sure our stay has been amazing and safe. We were there for hurricane Helene and they made sure we were taken care of the whole time. I can’t thank them enough, including Vince who is always on top of everything. Thank you from the bottom of my heart.

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 - 1/2 Mile to the Beach!
This condo was the perfect place to stay for my trip to Siesta Key. This condo is private in a neighborhood far enough from the hustle and bustle but close enough to get to the beach within a 5 minute drive. The condo was equipped with beach gear and all kitchen necessities. Very clean, comfortable, and felt right at home. I will definitely be booking this condo again for my next trip to my favorite beach!!

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!

Condo with a View 1: Beachfront!
Heidi is a generous, gracious host. From sending us helpful lists with restaurants and attractions to being available and responsive, she took care of us. We loved the location - beautiful quiet beach and the ocean just steps away. The pool below the palm trees. Great restaurants nearby. We loved our stay.
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- Anna Maria Island
- Siesta Beach
- Captiva Island
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Jannus Live
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Myakka River State Park
- Alafia River State Park
- South Jetty Beach
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