House holiday rentals in Siesta Key

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Popular amenities for house rentals in Siesta Key

House rentals with a pool

Top guest favourite
Home in Bradenton
4.98 out of 5 average rating, 57 reviews

IMG Academy-Modern Home Heated Pool Beaches 8 min

LeahRating, 5 stars4 days ago
Andrew was a very helpful and responsive host. The house was beautiful, clean and has described. we love Bradenton and will be back. Neighborhood was nice and quiet and location provided easy access to other areas.
Guest favourite
Home in Sarasota
4.97 out of 5 average rating, 58 reviews

2223 Doud Street, Sarasota, FL

MicheleRating, 5 stars1 month ago
This home was perfect for our group. We loved having 3 en-suite master bedrooms. The location is great for beach(Siesta Key), waterfront restaurants and shopping. We would definitely book again!
Guest favourite
Home in Bradenton
4.9 out of 5 average rating, 101 reviews

Large Sparkling Clean Pool Home West Bradenton

JesseRating, 5 stars5 days ago
What a wonderful place! I would like to thank the host for providing an exceptional and comforting stay for me and my family. I definitely recommend this place and would return in the future. Thanks for everything!
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.
Guest favourite
Home in Sarasota
4.94 out of 5 average rating, 98 reviews

Beautiful heated pool home, minutes from beaches

KatarzynaRating, 5 stars3 weeks ago
Great host and house. We enjoyed the layout of the house, awesome kitchen but the most we enjoyed the outside space and pool. Very nice neighborhood for walks in the morning. Easy drive to beaches, quick drive to grocery stores and restaurants.
Guest favourite
Home in Port Charlotte
4.92 out of 5 average rating, 139 reviews

Heated Pool Vacation Getaway

DannyRating, 5 stars3 days ago
very nice pool. great private quiet neighborhood, easy access to every thing. all was ‘as described’, sufficient & efficient. priced appropriately. good stay. clean. 🤙🏽recommended. ‘especially thrilled about Kuerig coffee maker as I brought pods. lol ☕️☕️
Superhost
Home in North Port
4.81 out of 5 average rating, 134 reviews

Luxury villa 4 bdr with a heated pool (14guests)

TroyRating, 5 stars2 months ago
Leyla's property was perfect for our stay. Came to visit our grandkids who lived in North Port and gave us a great spot to relax at the end of the night.
Guest favourite
Home in Venice
4.91 out of 5 average rating, 183 reviews

Vacation Rental with private swimming pool

MarieRating, 5 stars1 week ago
Great place to stay, convenient to all beaches, shopping and restaurants. I highly recommend staying here. Thanks Jan, I’ll be back for sure . Marie

Weekly house rentals

Guest favourite
Home in Venice
5 out of 5 average rating, 8 reviews

Pool - Tropical Retreat! Minutes to local Beaches!

RisaRating, 5 stars6 months ago
Olga’s listing was a perfect home for workcation. Has an office room, looks exactly the same from the picture, very clean, and they’ve got everything you need if you plan to cook. I take sleepy seriously and curtain kept room nice and dark in the morning. Movable shower head and instapot were added bonus for us where we were able to cook rice. Pool was super clean despite hurricane hits hard in the area, too. There has been minor issues here and there due to Hurricane Milton but Olga was very attentive and always promptly helped to solve the issue. Highly recommend to rent it if you plan to be in the area.
Superhost
Home in Bradenton
4.83 out of 5 average rating, 258 reviews

Comfortable & modern house in Central Bradenton

DesireeRating, 5 stars2 weeks ago
1. My stay at this Airbnb in Florida was great from start to finish. 2. The place was very clean and well-kept, just as described. 3. I didn’t experience any problems during my stay. 4. The host was responsive and always replied in a timely manner. 5. I would definitely stay here again and recommend it to others.
Top guest favourite
Home in Sarasota
4.95 out of 5 average rating, 165 reviews

Wood Street Retreat 4/2 Near Beaches & Downtown

JasonRating, 5 stars2 weeks ago
The place was great and very well located, easy to get around town. Very clean, plenty of space, and Wanda was extremely helpful and responsive. Highly recommend
Top guest favourite
Home in Indian Beach-Sapphire Shores
4.93 out of 5 average rating, 69 reviews

The Happy House - Seeing is Believing!

EmilyRating, 5 stars4 days ago
We absolutely loved everything about our stay! The house was a perfect fit for our family. The layout was great, comfortable rooms, kitchen was complete with everything you need for cooking. Our communication with Sheila was excellent. Will definitely come back again! Thanks for helping us enjoy a wonderful Spring Break!
Guest favourite
Home in Holmes Beach
4.9 out of 5 average rating, 58 reviews

Sea Glass Cottage

MadisonRating, 5 stars3 weeks ago
We loved our stay at Mike and Wendy’s bnb. Fantastic location with walking distance to the beach, the kids loved the pool which was kept very clean. The house was clean and comfortable, very home-y and did not feel like a rental, it felt like you were staying with a friend who lived there year round. Each room has its own bathroom which was very nice!
Top guest favourite
Home in Sarasota
5 out of 5 average rating, 19 reviews

Elegant Newly Remodelled Spacious HOME

SharonRating, 5 stars1 month ago
We loved this house, high end appliances and furniture! Everything was squeaky clean and very organized! Will definitely be back!
Superhost
Home in Sarasota
4.75 out of 5 average rating, 4 reviews

Amazing Location! Amazing Amenities!

JoniRating, 5 stars3 weeks ago
Jennifer offered a beautiful, clean home that was as described and perfect for our family! She was very accommodating and quick to respond! Our family enjoyed all the home and resort had to offer and can’t wait to book our next vacation using one of Jennifer’s properties!
Superhost
Home in Holmes Beach
4.88 out of 5 average rating, 108 reviews

New Golf cart + 4bd/3b w pool/2100 sq ft home

AugieRating, 5 stars2 months ago
Beautiful home and gorgeous location, we enjoyed the use of pool & golf cart. Host thought of many small things that made a big difference. Would recommend to others for great stay

Private house rentals

Superhost
Home in Bradenton
4.95 out of 5 average rating, 38 reviews

Now Booking for Summer - heated pool & grill!

DrewRating, 5 stars2 months ago
House was spotlessly clean and well maintained. We were really only sleeping there so did not use pool or backyard amenities. Would highly recommend. Only suggestion would be to have coffee and coffee condiments available on check in. Most Air BNBs I have stayed at offer this amenity.
Top guest favourite
Home in North Port
4.79 out of 5 average rating, 152 reviews

3 bdrm Pool Home / Quiet Cul De Sac

JeffRating, 5 stars3 days ago
Very nice home, plenty of space for larger family. We used the heated pool everyday. Stores within 5-10 driving minutes of property. Would definitely rent in future
Superhost
Home in Venice
4.91 out of 5 average rating, 56 reviews

The Ripple Inn At Fennario

TamaraRating, 5 stars2 weeks ago
Brian’s Superhost status is 100% accurate- he was great! The house was clean, easy to navigate and Brian was super responsive and gracious. The pool area is divine and the screened in porch overlooking the backyard was a great place to curl up with a book. We were within minutes of groceries, restaurants and shopping but the street was not busy or noisy. Definitely plan to stay again!!
Top guest favourite
Home in Sarasota
4.9 out of 5 average rating, 41 reviews

Sea la Vie - heated pool, 4b2b, stocked kitchen

JisungRating, 5 stars1 week ago
Great place for relaxing get together with friends. Pool and outdoor area was simply amazing. Close by the beach and downtown sarasota!
Superhost
Home in Longboat Key
4.88 out of 5 average rating, 120 reviews

Summer House longboat key

AndreaRating, 5 stars2 weeks ago
We had a wonderful stay at Chris’s house on longboat key! The pool was so nice for the kids and us adults to swim and relax by. The house was very nice and the beds were very comfortable. There were plenty of towels, extra sheets, and the kitchen was very well stocked with pot and pans. We did find it easier to drive closer to the crosswalk to the beach and park before walking across the street to get to the beach access. The beach was very quiet and beautiful. We found so many shells and our kids loved doing evening swims at sunset! It’s a very quick drive to Anna Maria Island and St Armand’s Circle. We really enjoyed our stay.
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.
Guest favourite
Home in Sarasota
4.94 out of 5 average rating, 128 reviews

Lake Front House with a Pool

BrittanyRating, 5 stars5 days ago
Spent a few nights with my husband and kids and was not disappointed. The house was just what we needed for a weekend of fun! The pool was the main highlight but the house provided lots of beach amenities that made our stay even better. Birute's place was not far from town and was located in a quiet neighborhood. Definitely recommend if you are looking for a peaceful place to spend time with the people you love and enjoy what Siesta Key has to offer!
Guest favourite
Home in Siesta Key
4.92 out of 5 average rating, 115 reviews

Siesta Peace Retreat a private home rental

Isabel CristinaRating, 5 stars9 months ago
Tracy's place is wonderful, and she is very attentive. She gave us lots of tips on what to do and where to go, which was a big plus. The backyard is very relaxing with a lovely spa where we enjoyed the evenings. The house was super clean, and the beds were very comfortable. If I return to Siesta Key, I will definitely stay there again.

Quick stats about house rentals in Siesta Key

  • Total rentals

    420 properties

  • Total number of reviews

    6.7K reviews

  • Family-friendly rentals

    390 properties are a good fit for families

  • Pet-friendly rentals

    200 properties allow pets

  • Rentals with a pool

    290 properties have a pool

  • Rentals with dedicated workspaces

    280 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key
  6. House rentals