342 Vacation Rentals in Osprey, Florida

“We had a great stay at The Oaks Club. The place was very clean, comfortable, and had everything we needed. What we loved most was that staying here felt like being a guest at a private golf club. The gated entrance adds an extra sense of privacy and security, and the security staff were always friendly, professional, and helpful. They gave us several great local recommendations that made our trip even better. The location was perfect for exploring the Sarasota area, beaches, and restaurants. Communication was easy, and everything went smoothly from check-in to check-out. This was one of our favorite stays in Florida, and we would happily return again. Highly recommend to anyone looking for a beautiful, relaxing getaway!”

“Small pleasant unit with lovely natural light overlooking a golf course and pool.”

“The property & grounds are gorgeous & safe! The space matched the pictures & description! It was a peaceful stay! I look forward to returning!”

“Sin lugar a dudas volveria”

“Very comfortable and located 10 minutes from the event I was attending in Siesta Key. I enjoyed the pool. And thank you for the "welcome" snacks and wine...it was a nice touch.”