
Holiday rentals with a pool in Siesta Key
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Top-rated rentals with a pool in Siesta Key
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Siesta Key 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.

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.

Private Heated Pool & Spa. Walk to Shamrock Park.
Ryan’s place was just right for our escape from the Wisconsin winter! We walked every morning to the Shamrock park and Nature center. Great restaurants and shopping in Venice.
Apartment rentals with a pool

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

Condo With Heated Pool, Beaches Only Minutes Away
We were pleasantly surprised by Nicole’s apartment. It was extremely clean, lots of towels, linen, well appointed kitchen and everything else needed to make it like home. We didn’t need to buy or bring anything for the beach because we had beach chairs and an umbrella which were in really great shape. The apartment is within a short driving distance to beaches, stores, restaurants and shop. We had a great time and felt right at home. We highly recommend her place to anyone vacationing in the 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.

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!

Sun, Beach Views, and Smiles!!!
We hated to leave! It was perfect for our stay. Very clean and steps away from the beach, close to everything store wise/ restaurants.

Lovely 2 bedrooms condo with pool in Boca Ciega
Matt was the best at explaining everything and. Was so quick. To respond and answer and questions I had as well as give me great info around the area. Would rent from him again for sure and recommend him to anyone looking for a great place and helpful with any questions you might have.

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
Quick stats about holiday rentals with a pool in Siesta Key
Total rentals
1.4K properties
Nightly prices starting at
£45 before taxes and fees
Total number of reviews
24K reviews
Family-friendly rentals
1.2K properties are a good fit for families
Pet-friendly rentals
210 properties allow pets
Rentals with dedicated workspaces
670 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