Search Vacation Homes in Osprey

"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "

"We were centerally located and had an easy drive to the beach and park. "

"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"

"It looks just like the pictures and the sunset daily is absolutely gorgeous. The neighborhood is nice and the people are kind. We loved being short car rides away from stores, beaches and the legacy trail. The owners had great communication. Would definitely stay again."

"Very clean and tucked away in a quiet little neighborhood with everything you need within 10 mins...this place made for the most comfortable and perfect vacation!"

"The cottage was comfortable and the pool was relaxing. "

"My family and I had a great stay. The property was great inside and out. "

"Traveled with my kids and this place was so great! Super cute and comfortable. We loved the Mermaid Tiny House."

"The Tiny House is a perfect location to explore Siesta Key and the surrounding areas. It had just what we needed but was in close proximity (walking distance) to many bars and restaurants but was still exceptionally quiet."

"It was great to be close to the beach and lots of restaurants and shops."

"My family and I loved it! Very close to the beach! We will definitely book again!"

"Family had a great vacation at this property in Gulf Gate. Very nice pool and deck area and comfortable and clean home, great location for Siesta and Turtle beaches. Host was responsive and a pleasure to deal with, check in/out very simple. We were happy with our stay. "

"Great stay, good location, attentive host!"

"Exactly what we were looking for. A place near the beach with a pool. Clean, modern, attentive manager. Would recommend highly."

"Clean, reasonable price and close to everything."

"Our family of 11 had a truly wonderful stay. The pool was most definitely a highlight."

"Clean and great location! Would stay again! "

"Nice stay perfect location"

"It was very clean and close to the beach. Perfect location."

"The place was super cute, clean, quiet, cozy, and in a great location. The host was very communicative and sweet. Definitely a great stay, 10/10 recommend!"