
Holiday rentals with a pool in South Sarasota
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Top-rated rentals with a pool in South Sarasota
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Popular amenities for South Sarasota rentals with a pool
House rentals with a pool

Vitamin Sea: Private Pool, Downtown, and Beaches!
My family and I stayed here for 10 days and we can say it was one of the best stays. Our flight landed early and we reached out to the host to ask for an early check in, they responded back fast and were able to accommodate us. Once inside the house everything was clean and the kids went right into the pool which was also very clean. Overall we felt right at home and the whole stay was 10/10!

3bd 2th Solar Heat Pool Large home W/ big yard
Absolutely gorgeous home. It actually felt like home away from home. My teenage boys were very chill and relaxed. I loved the fact that there were two living room areas.. that way my teens could play their gaming system in one and my toddlers could watch tv in the other. My two toddlers are still asking when are we going back to our new home. lol

Centrally located oasis.
The place was mostly what it said it would be, the pictures are accurate. Was pretty nice and cozy. Had lots of privacy, which was really nice. House was clean and had all of the amenities that were promised. Bed was really comfortable. The only drawback was that the pool was a little dirty, looked like it hadn’t been cleaned for a few days before we got there but it wasn’t that big of a deal.

Lovely pool house 5 minutes from the beach
Had a lovely stay here. Communication with Carmen was fantastic. Decorating in home was tasteful and lovely and we felt right at home.

Spacious 4BR Getaway – Perfect for Families!
We will remember the pool! Private, clean, nice landscaping, and plenty of seating around the pool deck. This property is conveniently located to restaurants, shopping, beaches, all adventures. There were no surprises and a wonderful get-away from the Minnesota snow! There were a plenty of beach chairs for our crew as well as sand toys for the kids. This house has many extras that made our stay more enjoyable.

Large 4 bedroom pool home tiki bar close to Ami
We were able to book a 3 night stay last minute and the hosts were super easy to work with. The house was more than we needed and everything available to make our stay enjoyable. They were quick to respond and answer questions. House is super clean and location allowed us to get to the beach and away from it when needed. We appreciate the space that allowed us to relax and unwind after a busy week.

Tropical Pool Vacation Getaway!
Beautiful place to stay. Kitchen was well equipped. Only couple complaints (if you call it that)…my husband and I would have liked to see full beds in the bedroom with twin beds, maybe a few bath and kitchen towels, a dresser in the spare bedrooms sure would have been nice to put clothes in or suitcases on, maybe a tv in each bedroom, the garage door opener didn’t work. Sounds spoiled but just what we are used to. Pool was absolutely amazing!! Gas grill worked just great!

Cozy Home with Heated Pool
The house was very nice and comfortable and the Host Elina was very responsive and helpful. Would recommend and would stay here again.
Apartment rentals with a pool

Lovely Condo, Heated Pools, AMI, IMG, Top beaches
Perfect service, very friendly, comfortable and well-located area

Z. Water front condo, Via Roma, ground floor
This is a comfortable and clean apartment on one of the best spots on the island. The hosts were great, highly recommend.

1 block from beach + pool - Cayman Cay #102
This place was PERFECT! Beautifully decorated to match the beach aesthetic. Literally a one minute walk to the beach! I loved that the place had plenty of towels (both bath and beach), every kitchen utensil and cooking dish you could think of. (We travelled with a teen, a 6 year old and a 10 month old for a week so we cooked a lot.) There was plenty of bedding to use (we enjoyed being able to bring the kids out to the living room and use the pull out sofa for a family movie/game night). There were board games there to use and the biggest plus was the owner was nice enough to allow us to use the accessories he had for the beach at no additional charge. (Beach wagon, chairs, umbrellas, toys, floats). WiFi worked great. AC worked great. Communication was seamless! Told my spouse I couldn’t wait to go back again. Russell and Cindy were incredible to work with. Highly recommend!

Lovely 2 bedroom condo with pool & tennis courts
This condo was even cuter in person than it was in the photos. It was super clean, safe, spacious, had a gorgeous screened in balcony that looked out over the pool, and was centrally located really close to groceries, restaurants, multiple beaches, and more. We stayed here as a family of 4 and the kids had their own room and bathroom and we had a master with en suite. I saw another review that said there is a little noise from the busy road outside but you really only notice it if you're trying to sleep with the windows open. We originally booked a hotel that ended up being awful so I found this place last minute and they were able to get us in the very next morning. They let us check in early since we were kind of stranded, and walking in was like a breath of fresh air. Highly recommend this place for 2-4 people!

Siesta Village Short Walk to Beach w heated Pool
This place was fantastic with everything we needed. It was close to everything and a short drive to some of the other local activities. Short walk to multiple beach entrances and a cart, chairs, umbrella, etc. was all available to take to the beach. There’s a local shuttle that takes you all over the island for free and a market around the corner that’s fully stocked with everything you need to cook some meals there. We did the night time LED kayaking and then did the Mangrove Eco Tour with Kayaking SRQ, ask for Kaleb for the mangrove tour, the man knew everything about the area, its history, conservation, and gave some great restaurant and attraction recommendations in the area. Or… just hang out at the beach. We were there during tropical storm Debby and Kathryne communicated with us throughout. Absolute amazing stay… even with a tropical storm! We can’t wait to come back.

Shorewalk upgraded condo upstairs unit 4415
Enjoyed our stay. Very quiet location and convenient to everything

Lakeside Condo. Beaches, Restaurants, IMG nearby.
Great place to stay! It was exactly the way a rental place should be. A very clean and comfortable place to stay.

Peaceful retreat, pool, hot tub, near Siesta Key!
Suzanne was very responsive, the residence was clean, spacious and well equipped. Will definitely stay again.
Quick stats about holiday rentals with a pool in South Sarasota
Total rentals
210 properties
Nightly prices starting at
£38 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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- Crescent Beach
- John's Pass
- Cortez Beach
- Bean Point Beach
- Lido Key Beach
- Amalie Arena
- Raymond James Stadium
- North Beach
- Vinoy Park
- Coquina Beach
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Myakka River State Park
- Tropicana Field
- Van Wezel Performing Arts Hall
- Lakewood National Golf Club
- Splash Harbour Water Park
- Jannus Live
- Sunken Gardens
- Englewood Beach
- River Strand Golf and Country Club