Holiday rentals with a pool in Siesta Key

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Popular amenities for Siesta Key rentals with a pool

House rentals with a pool

Superhost
Home in Sarasota
4.63 out of 5 average rating, 19 reviews

Vitamin Sea: Private Pool, Downtown, and Beaches!

LindaRating, 5 stars9 months ago
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!
Guest favourite
Home in North Port
5 out of 5 average rating, 20 reviews

3bd 2th Solar Heat Pool Large home W/ big yard

Ja'Vaunna Rating, 5 stars2 weeks ago
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
Superhost
Home in Sarasota
4.93 out of 5 average rating, 135 reviews

Centrally located oasis.

JacobRating, 5 stars9 months ago
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.
Superhost
Home in Venice
4.56 out of 5 average rating, 16 reviews

Lovely pool house 5 minutes from the beach

LindaRating, 5 stars12 months ago
Had a lovely stay here. Communication with Carmen was fantastic. Decorating in home was tasteful and lovely and we felt right at home.
Superhost
Home in Bradenton
4.87 out of 5 average rating, 291 reviews

Large 4 bedroom pool home tiki bar close to Ami

JohnRating, 5 stars2 weeks ago
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.
Superhost
Home in North Port
4.81 out of 5 average rating, 43 reviews

Tropical Pool Vacation Getaway!

JosephRating, 5 stars1 month ago
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!
Top guest favourite
Home in North Port
4.85 out of 5 average rating, 13 reviews

Cozy Home with Heated Pool

EricRating, 5 stars2 weeks ago
The house was very nice and comfortable and the Host Elina was very responsive and helpful. Would recommend and would stay here again.
Superhost
Home in Venice
4.88 out of 5 average rating, 17 reviews

Private Heated Pool & Spa. Walk to Shamrock Park.

MarcieRating, 5 stars1 month ago
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

Guest favourite
Apartment in Bradenton
5 out of 5 average rating, 10 reviews

Lovely Condo, Heated Pools, AMI, IMG, Top beaches

Luis AlbertoRating, 5 stars2 weeks ago
Perfect service, very friendly, comfortable and well-located area
Superhost
Apartment in Englewood
4.87 out of 5 average rating, 47 reviews

Condo With Heated Pool, Beaches Only Minutes Away

DanRating, 5 stars2 weeks ago
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.
Superhost
Apartment in Bradenton Beach
5 out of 5 average rating, 5 reviews

Z. Water front condo, Via Roma, ground floor

JennieRating, 5 stars27 months ago
This is a comfortable and clean apartment on one of the best spots on the island. The hosts were great, highly recommend.
Guest favourite
Apartment in Osprey
4.92 out of 5 average rating, 12 reviews

Lovely 2 bedroom condo with pool & tennis courts

CariRating, 5 stars1 month ago
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!
Superhost
Apartment in St. Pete Beach
4.88 out of 5 average rating, 147 reviews

Sun, Beach Views, and Smiles!!!

KendraRating, 5 stars3 months ago
We hated to leave! It was perfect for our stay. Very clean and steps away from the beach, close to everything store wise/ restaurants.
Guest favourite
Apartment in St. Petersburg
4.91 out of 5 average rating, 23 reviews

Lovely 2 bedrooms condo with pool in Boca Ciega

JohnRating, 5 stars9 months ago
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.
Guest favourite
Apartment in Siesta Key
4.87 out of 5 average rating, 101 reviews

Siesta Village Short Walk to Beach w heated Pool

CoryRating, 5 stars8 months ago
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.
Guest favourite
Apartment
4.84 out of 5 average rating, 126 reviews

Shorewalk upgraded condo upstairs unit 4415

BrianRating, 5 stars2 months ago
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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