Compare Vacation Rentals & Rent By Owner Homes in Osprey, Florida, USA
About Osprey Vacation Rentals
With more than 121 Osprey vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Osprey.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Osprey, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Osprey. Places to stay near Osprey are 773.77 ft² on average, with prices averaging CA $403 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Osprey with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Osprey, FL
Frequently Asked Questions About Osprey?
What are 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
- Sarasota Vacation paradise!
- Pet-Friendly Modern Retreat Near Siesta Key
- Furnished and meticulous! Near Nokomis, Venice and Siesta Beaches.
- Sunny Coastal Escape
- Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM
- Private guest house with king bed & loft. Deck with hot tub and putting green
- Windsor Lodge Unit 10, Studio, close to the beaches, pool access
How many Rentbyowner vacation rentals are available in Osprey?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 121 in the Osprey area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Osprey.
Nearby Neighborhood (5)
| Neighborhood | Property Count |
|---|---|
| Vamo Vacation Rentals in Sarasota, Florida | 47 |
| Palmer Ranch Vacation Rentals in Sarasota, Florida | 37 |
| Sorrento Shores Vacation Rentals in Sarasota, Florida | 577 |
| Bay Acres Vacation Rentals in Sarasota, Florida | 721 |
| Rivendell Vacation Rentals in Sarasota, Florida | 395 |
