Owner Direct Vacation
Rentals in Osprey

There are a lot of options in Osprey. If you plan on staying in the Osprey area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Osprey:

• Mid-century Waterfront Home with pool
• Rare private beachfront estate on the Gulf.
• 2-bedroom Spacious townhome in Osprey
• Pet-Friendly Modern Retreat Near Siesta Key
• Furnished and meticulous! Near Nokomis, Venice and Siesta Beaches.
• Sarasota Vacation paradise!
• Sunny Coastal Escape
• Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM
• Windsor Lodge Unit 10, Studio, close to the beaches, pool access
• 2 Bedroom Ground Floor Condo in Osprey - lots of light & beautiful water view!

There are 9 vacation rentals with private pools near Osprey. Top-rated homes that have access to a swimming pool include:

• WATERFRONT Luxury Home! Private Pool, Dock, Close to Beaches
• 15 mins from Beautiful Siesta Key Beach, Waterfront Home w/Private Pool
• Gorgeous Updated Heated Saltwater Pool Home, WiFi, Dog Friendly, Kayak Launch & Park, Garage
• Tropical canal front home in Osprey

If you are looking for a family-friendly vacation home in Osprey, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Osprey:

• Charming Secluded Tented Cabin in Sarasota, Florida
• Windsor Lodge Unit 18, studio, close to the beaches, pool access
• Heated Pool | 3 Beds | Near Beaches and parks

Currently, the total number of properties listed in 2026 is over 124 in the Osprey area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Osprey.