
Vacation rentals with a pool in South Sarasota
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in South Sarasota
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for South Sarasota rentals with a pool
House rentals with a pool

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
A beautiful home with a private, relaxed atmosphere and all the amenities you could need.

Luxury 3/3 with Heated Pool, Spa, & Putting Green!
My wife and I had a great time at this stay. Lots to do at the house along with great beaches and restaurants within a 15-20 minute drive. The house was clean and had everything that you might need. We were able to drive to Disney in just over an hour and a half which provided a different experience to go along with the daily beach/pool trips. Cool AC inside to combat the humid 88 degree weather in June 2025.

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.

Waterfront Home w/King Studio & Pool, by Siesta
The home was perfect for our family. Plenty of space and the in law suite was amazing. Everything was very clean and well maintained. While our girls enjoyed the pool, our boy was casting his fishing pole from sun up to sun down. It is located in a very quiet peaceful neighborhood, yet close enough to the tourist areas to drive to them in 10-15 minutes. Amy is absolutely a 5- star host and if we’re ever in the area again, we will ABSOLUTELY book this home again.

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.

Beautifully Remodeled Home with Pool Near Siesta
You will not find a better host. We mentioned that we were celebrating a birthday and Yekaterina went above and beyond what we could have even thought of! She surprised us with all of the finishing touches. She made our stay so special! Her place is amazing! The location, the space, EVERYTHING. She is absolutely incredible and we can't say enough about Yekaterina, her place, and our stay. We have been to a lot of airbnb's and many very nice, but Yekaterina is the absolute best host you will find. You will not be disappointed! This is definitely at the top of our list of "Places to stay and visit again!" Thank you Yekaterina!

Lake Front House with a Pool
This house was spotless, organized and had a loaded kitchen! It is in a amazing location near the beaches and the house came loaded with beach equipment. I would love to come back. Birute was very helpful with us and responsive in timely manner Thansk for all!
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!

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.

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!

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!

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!

Siesta Key Beach Front Condo
Our stay was exactly what we wanted. Our host, Evan, was great and quick with any questions we had. The condo was located very close to Siesta Key Beach, and we didn't have to drive more than 20 minutes to get to anything that we wanted to around that area, some things even within walking distance. Everything we could have possibly wanted was provided in our home, which really made the week stress-free. We would definitely stay here again!

Lido-Key- Tiny Studio Holiday Cottage-A
I consider myself a seasoned veteran traveler… So when I walked into an Airbnb in Lido Beach, I wasn't sure what to expect actually. I pleasantly surprised. Unit number 12 is perfect for me. located in the corner of the small property where multiple units were located. Nice pool, nice shaded paths excellent landscaping it just felt good to be there :-) Every time I travel, I take an assessment of the things I need to go buy. You know simple things the kitchen or for a walk to the beach. This team had everything including the beach chairs. I would highly recommend this property. This host in this area. I just purchased a property in Sarasota area and I will try to use this spot again as my secret getaway. Awesome 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
Quick stats about vacation rentals with a pool in South Sarasota
Total rentals
210 properties
Nightly prices starting at
R897 ZAR before taxes and fees
Total number of reviews
5.7K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
150 properties have a dedicated workspace
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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