Osprey Vacation Rentals

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Make Osprey your next getaway

Prepare for coastal living by staying in an Osprey, Florida vacation rental. Situated south of Sarasota on the Gulf Coast, the area is known for its beautifully preserved parks and Spanish history. And while it maintains its pioneer roots as a bastion of “Old Florida,” it’s evolved into a more laid back destination that keeps guests close to the beach and surrounding nature.  

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Osprey vacation rentals for every getaway

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Osprey Frequently Asked Questions

Yes. 55 of our Osprey vacation rentals have internet access, so you can stay connected throughout your trip.

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Some of the most popular amenities in our Osprey vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Osprey team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Osprey, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Explore our Osprey, FL vacation rentals

Coastal and comfortable, the vacation rentals in Osprey, Florida are designed to capture the historic charm of the community while placing guests close to the best activities in the area. Pick between relaxing retreats on the beach or accommodations perfect for family trips. 

Nearby, your Osprey, Florida vacation rental, you’ll find Blackburn point Park, the Marie Selby Botanical Gardens, the famous Historic Spanish Point, and so much more, including kayak and boat rentals. Enjoy your vacation in Florida—you deserve it.