Family-friendly vacation rentals in Siesta Key

Kayla’s listing exceeded all my expectations. From the moment I booked, communication was seamless and welcoming. The space itself is beautifully decorated, spotless, and thoughtfully equipped with everything you might need for a comfortable stay. The highlight was definitely the pool — it’s great! Perfectly maintained and a fantastic spot to relax and unwind. The heated jacuzzi is also awesome — it’s perfectly functional, warm, and incredibly relaxing, making it a true standout feature of the property. The location is superb — just a few minutes’ drive to the most amazing beach in the USA! It’s the perfect base for exploring and enjoying the beautiful surroundings. Kayla was a wonderful host—friendly, attentive, and genuinely eager to ensure we had a great experience. She provided helpful local tips and made us feel right at home. I highly recommend Kayla’s listing to anyone looking for a cozy, convenient, and memorable stay with fantastic amenities. I can't wait to return!

Clean and neat, friendly and when we wanted to extend was quick and easy to enjoy our stay longer. Thank you again

We enjoyed our stay at Kathleen’s home. This was our first time coming to AMI since the hurricane. Kathleen was sure to send updated photos of the interior following repairs. There were still some repairs needed on the exterior (various exposed construction and holes in soffits). However this did not significantly impact our stay. The home was clean and the kitchen was well equipped. We appreciated the natural shower gels, shampoo and abundance of sunscreen. There were numerous beach toys as described and the beach wagon came in handy. The space felt a little tight with two families (with somewhat older children) but would be perfect for young kids given the quantity of toys and activities. We had an issue with the interior locks at one point but this was handled well by the host. Overall we had a nice experience. Thank you!

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.

Romualda’s home was very clean, beautiful, and modern. She was very communicated from the time we booked the AirBnb, to the time we checked in, and the time we checked out. We felt right at home as she had many ameneties that were offered and more. We will definately book again next time we are in town.

Quick and easy to get to! We used the pool a lot, would highly recommend staying here. Quiet area and within a 1/2 hour of the beach! We’ll be back next year!

We enjoyed our stay at the Pink Flamingo house. The house was well supplied, and clean. I would definitely recommend this house for any one that has a bigger family to accommodate for. The children enjoyed the heated swimming pool. Yvonne was very easy to work with and always responded when we had questions.

Paul’s house is in a very quiet neighborhood. We found the house clean, the kitchen was well stocked, there were nice beach chairs and beach towels to use and the pool was well heated. The beds were comfortable with nice linens. Paul was quick to respond to our question we had. It’s definitely a place we will stay again.

Sheron was a wonderful host! The airbnb was exactly as pictured on the app. It's clean, comfortable, and Sheron thinks ahead (she even left us tide pods to do laundry). It's also in a quiet neighborhood, which was amazing. However it's located in a neighborhood where you can access different experiences easily. Also, one of our favorite things was the binder Sheron left for us, there were so many recommendations and we actually did 3 of the recommendations. Oh, and my favorite thing, the beds are so comfortable. I always have trouble sleeping the first day or two or a vacation. I didn't have that issue here, I slept so well the 4 nights I stayed. I recommend booking!

Great place and excellent host. Loved the pool and watching the egrets by the lake. Thank you Tomas!

I visited Sarasota with my family from the state of Rhode Island from April 4 to April 7 and we stayed at Jason’s & Laura house and it was an amazing experience. The house was very clean and organized. The house is located on a great neighborhood, super safe and great amenities. The house was stocked with beach supplies like beach chairs, beach towels, a boogie board and a beach cooler that was so nice. The house was exactly what we were expecting, I would recommended to everyone. Thank you Josh and laura.

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!

Overall, this is a wonderful place to stay. The house provided plenty of room for our family of six adults and two kids. There are several nice features in the home including multiple deck spaces to relax in and a large pool and hot tub. The house was very well equipped and organized. Also, the location was away from traffic noise and advantageously situated on the north end of the Key avoiding the heavy traffic that occurs on the south end. Better advanced communication and more prompt responses to a few issues we discovered upon arrival would have made the experience more enjoyable. In the course of our month long stay we were able to address most of the issues and the host accommodated our concerns. We are planning on staying again next year.

Great stay! Everything was neat, clean and ready for our stay! Would stay again!

Niconle was a wonderful host. She communicated frequently and made us feel at home. The location is peaceful. The lanai faces a pond with frequent visits by many different shore birds. The kitchen is well equipped. We would stay at this location again.

We loved the apartment. Lots of room for the whole family. The kitchen was stocked with everything you need to cook. We loved having the two bathrooms next to the bedrooms. The whole place was very comfortable. We really enjoyed it all. There were a lot of trucks in the morning near the 7-Eleven across the street, but it was still worth it to stay there. Great price for the accommodations!

This is our second year of staying here. Our hosts were very helpful and even left us little treats to welcome us. We arrived on November 8th, 2024. Weeks prior to arrival, they kept us updated on the progress of Hurricane cleanup. Their home is the perfect location. You can enjoy the ocean just across the street or the pool and hot tub with a view of the channel. Their home is clean and includes so many items that would need on this vacation. They were always willing to answer our questions as well as suggestions to make our trip even better. We feel perfectly at home here and can't wait to return next year.

My husband and I, along with our 3 kids, had the best quick getaway at Leticia’s Place! The duplex is only about 50 feet away from the beach, and we were lucky enough to have the place to ourselves. It was so easy to go back and forth from the beach to the house for lunch, naps, or to just watch the sunset! The trolley stop is just around the corner, but we drove to most of the restaurants and shopping. The island is small, so getting around is very easy. With small children, we were grateful to only be steps away from the beach! The kids absolutely loved the pool, and spent just as much time in it as they did on the beach. The pool area is absolutely beautiful and kept mostly shaded from the sun, so it was nice to cool off down there or have a night swim after spending the day at the beach. Leticia was very responsive and made sure we had the best possible stay. We can’t wait to go back, and would absolutely stay here again!

This was our second stay in this stunning home. Jennifer and Amy were excellent to work with. They respond to communication promptly and authentically cared that we had the perfect stay. The home is beautiful and had everything we needed. My husband and I are already talking about returning. Highly recommend!!!

She’s Always Right is a spacious home that is better than the pictures show. Home was well fitted with all you may need during your stay and plenty of beach items. The house was clean, which we are usually picky about. This wasn’t our first time in the island so we knew what to expect but the property managers were great at communicating and suggesting things to do and places to eat. One thing that was a nuisance (though we never raised the issue) was that the plugs in the bathrooms didn’t work. We had a wonderful time and would definitely come back to this rental.

We all had an amazing time staying at Transfer's Haven. The AirBnB was super easy to locate, get inside, and matched the description. The space itself was super clean and accommodating, and the area was perfect. I would absolutely stay again.

We had a wonderful visit to Casey Key while staying at Christopher and Michelle's place. The pool and hot tub are great amenities and the house was perfect for our needs. Everything was clean and comfortable and the hosts were quick to respond to any questions we had. We hope to return soon!

We loved our Spring Break stay at Helen and Hannah’s condo. The condo and the complex are beautiful and everyone was very friendly. A lot of retirees were around for the week, but a few families too. Our 15-year old enjoyed it too and we made daily use of the tennis court, pool and grill. The location is very convenient and is a bit away from the main Spring Break area and beach, but we like the peace. Thank you very much and we’ll consider returning again.

We loved the pool and hot tub. Ben was very responsive when I asked about if there was a speaker we could use and he dropped one off at the front door within minutes. Great location and price was reasonable. We would Definately stay again!