Family-friendly vacation rentals in Osprey

Beautiful historic home ! Loved the wrap around porch and the hot tub. Great shower ! Loved the coffee and wine and cozy blankets on the couch . Wish we could have stayed longer . Lots of space ! Close to downtown fort Myers

Just returned from another great stay at Kayla’s place. Everything was fantastic, the backyard pool and jacuzzi were amazing. We also really appreciate Kayla’s responsiveness. Looking forward to returning next year!

Super clean, quiet, comfy bed. We enjoyed the bayside pool. Nice views. Palm Bay club nice benefit as after a short walk over to the beach we enjoyed the chaises delivered and set up close to the water and hole drilled for our beach umbrella. Amazing sand is not over rated. Warm gulf waters and easy entry and exit. Breeze Trolley with their app made getting around without driving convenient . Lots of fun food and shops minutes away. This bayside spot a was a delight.

Absolutely loved our stay! The place was spotless, beautifully decorated, and had everything we needed for a relaxing getaway. The location was perfect—just steps from the beach with stunning views and peaceful surroundings. Cindy was incredibly responsive and welcoming. We’ll definitely be back—highly recommend

Our stay was amazing, Ven was a great host, unfortunately there are always minor issue that come about when staying in properties but their communication was so great it over shadowed all of our concerns! Thank you for the stay!

We enjoyed the villa. It was close to Siesta Keys. There were a lot of restaurants close by

We had a fantastic stay at this home! Our family of five (2 adults and 3 kids) absolutely loved it. The house was clean, well-maintained, and located in a perfect spot—just a five-minute walk to the beach. It had everything we could possibly need, from kitchen essentials to beach toys for the kids. What really made the stay special was Dave’s hospitality. He was incredibly responsive and provided excellent recommendations for local beaches, restaurants, and more. His tips really helped us make the most of our trip. We highly recommend this place and will definitely be back!

Our family really enjoyed our stay at Daniel’s condo in Bradenton. It was very clean, updated, quiet,and spacious with great amenities in the complex. We highly recommend this rental to couples or families. Daniel also provided perfect communication and local recommendations. Very convenient area with great access to grocery and 15 minutes to beaches at Anna Maria Island.

Maggie’s place is perfect!! So convenient to everything you need!! Everything in house that you would need and also everything you need to go to the beach!!! Maggie is very fast to responding to any questions you have!! 5 star for sure!!

Will definitely stay again if I ever come back this way. I wanted a place that had a private pool and was pet friendly. I got both. The neighborhood is peaceful. The house is very spacious and clean. One downside, there is no tv in the master bedroom but that was fine too. Don’t need to be in bed with a pool like this one. Thank you for allowing me to stay.

This place was a great home away from home for the week! It was clean, comfy, and cozy. It was in a great location, being about a 10 minute walk from some of the best local restaurants, and about 15 from downtown! We found a great breakfast spot I would highly recommend, called The Breakfast Company. Would definitely stay there again!! Great price and Erin was a great host with prompt and helpful responses when needed!!

We had a wonderful time in Sarasota. Maureen and Patrick are clearly hosting pros. The kitchen was well-stocked, so we cooked most of our meals, made coffee/tea in the mornings, and kept groceries from the nearby Publix in the fridge. We enjoyed making dinner and sitting out on the screened in porch. The neighborhood was very residential and safe. The bathrooms and bedrooms were well-stocked and comfortable. Five college girls slept comfortably across the three rooms and I would say one more could definitely have fit as well. The house had a carport with a washer and dryer with detergent, beach chairs, umbrellas, and puzzles. Even when it rained, we enjoyed sitting in the house and reading because the space was relaxing and comfortable If you’re planning on going to the beach, download the Bayrunner/Breeze Rider apps to catch the free trolley. The trolley was a short walk away through the neighborhood and we enjoyed riding to the beach every morning.

Beautiful home, lovely host, very close to the beach. Home was very clean and welcoming. Would come back

This was our second time staying at Lubos pool house. We really enjoyed our stay and are already looking far time to escape back. Great location near restaurants, stores and beaches. Back yard and pool are a dream and very peaceful.

Excellent host! Would stay again! Great location and great home!!

We had an absolutely wonderful stay at Sheila's place! The location was perfect, close to everything. Sheila was incredibly responsive and helpful throughout our stay, answering all our questions promptly. We highly recommend staying here!

We had a very good time at Siesta Key and enjoyed our time at Maureen's place. The building is older, the amenities are well maintained and the condo itself is well cared for. I did find some mystery stains on the mattress and the decorative pillows in my room, but I'm guessing they are just spills that were difficult to get out. More importantly, the boat dock is usable, albeit with some difficulty if the boat is larger than 22 feet or so. We figured out on the second day that the best way to dock was parallel to the intracoastal between the posts and to tie off with lines on either side of the stern and with a single line on the bow. I would check ahead to make sure the dock is available, but we had no other boats docked there on a holiday weekend. The private beach access was a lifesaver on a holiday weekend, despite the short walk required to get there. Having both intracoastal and beach access is the biggest value of the place in my opinion.

Such a beautiful stay with all the amenities, clear instructions and a clean place with everything you need surrounding you. Beautiful home, I appreciate the stay!

This place was perfect for two couples and close to the beach etc The beds were comfortable and check in and check out easy. We would stay here again

Solen was an amazing host—very responsive, friendly, and helpful throughout our stay. She even brought us a brand-new can opener when we needed one! The house was spotless, cozy, and located in a great area. We had a wonderful time and would definitely stay again!

Great place, clean, and a very easy walk to the beach and local restaurants.

Perfect spot right across from Sarasota Beach! Quiet, very clean, great pool, and very responsive host! We loved our stay and have favorited Vanessa as a host so we can check out her properties when we come back. Highly recommend this host and property for your trip to Siesta Key.

Great home, close to the beach and had a ton of fun.

Fantastic value in a perfect location Host was very friendly and responsive Private with a super comfortable bed!! Highly recommend