Family-friendly vacation rentals in Osprey

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!

Can’t say enough good things about the house and Steven. The house was beautiful, it was everything we could’ve wanted and to have the additional beach supplies readily available was amazing! Steven answered so quickly and was happy to help however he could. 10/10 for us!!

We had an excellent stay here. The location was excellent as it was right on the Gulf. Our family loved the screened-in lanai. The lanai is right off the master bedroom, so we would open the slider and listen to the waves as we fell asleep. Beach was beautiful and just steps away. Cindy was very kind and messaged me during our stay to see if we needed anything. The condo was spacious, and there was lots of room for storage. Condo has great location- less than 4 miles to Publix and close to restaurants/shopping at St Armands Circle. We would love to stay here again in the future and definitely recommend!!

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!

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!

Amazing, clean place. Great pool

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

Beautiful spot, not far from numerous restaurants and things to do. Not far from the Charlotte Event Center. Good amenities, stocked cupboards (coffee filters, seasonings, etc). Definitely would stay here again if we visit.

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!

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.

Chris was a very responsive host. During our stay he spent a day working on his boat in the back. He was very friendly, but also respected our privacy. The house met all of our expectations and our kids loved the pool. The neighborhood was great to walk through and each house offered fantastic curb appeal. With 3 kids under the age of 6, the 10-12 minute walk to the beach was a little long, but Chris’ wagon and beach supplies helped! The golf cart would have been ideal, but without a place to park near the beach we didn’t have much use for it. We thoroughly enjoyed our stay and the entire family agrees we’d love to go back. Thanks Chris!

Such a lovely stay! Very homey and well decorated without feeling cluttered. Loads of room to spread out and terrific natural light. The beds were extremely comfortable. We were delighted by how walkable the neighborhood was and the street is super charming and quiet.

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.

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.

Lisa and Robert not only are great host but very nice and communicative as well!. The place it’s very nice cozy and quiet for a good time to rest.

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

This is an incredible house. The location is perfect and private. We had our little pug with us and it was exactly what we needed. The pool is warm and clean and very enjoyable as the sun goes down. The bed was super comfy and the kitchen well appointed. I’ve stayed at a lot of rentals and this is one of the best. If you’re looking for a rental just book this one. You won’t be disappointed.

Lovely quiet neighborhood, extremely clean. The decor is a little out dated & probably needs a little brighting up. But we have no complaints about our stay. Very happy!!!

We had a great time! the pool was amazing, everything was very clean and we had everything that we needed while we were there.

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.

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!

This was the cutest home and was absolutely perfect for our stay. The home was clean, well stocked, and in a quiet neighborhood. The pool was crystal clear. The beds were comfortable. The listing was just as described. We truly enjoyed our stay!