Osprey villa rentals

We found 356 villa rentals — enter your dates for availability

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in a villa rental in Osprey?
Prices vary depending on length of stay, time of year and property location, so enter your holiday details to discover what's available. Whatever your budget or plans, Stayz has villa rentals in Osprey for every type of guest.
When is the best time to rent a villa in Osprey?
The perfect time to visit Osprey depends on factors like activities that you want to do and which season you prefer to go. With average temperatures ranging between 14ºC and 20ºC, January is a popular month to stay in a villa rental in this part of Sarasota County. Want to truly experience this destination? Check for any local festivals or events and arrange your villa rental stay around them.
Where can I rent an Osprey villa with great views?
One of the best ways to find an Osprey villa with views is to use our handy filters. Narrow your search by "Location" or select "Guest rating" to view places other Stayz guests recommend. After all, why settle for a room with a view when you can have an entire villa rental with stunning vistas?
Can I book a luxury villa in Osprey?
Take your holiday to the next level with one of our villa rentals in Osprey. Often boasting modern conveniences like gourmet kitchens, high-tech home entertainment systems and plush furnishings, you and your guests will feel like VIPs. Use Stayz's filters to display the properties with high-class perks like hot tubs and pools for that added layer of opulence and luxury.
What are the top things to do in Osprey?
One of the first things to do after securing your villa rental is to fill your itinerary with exciting activities and sights. There's loads of them in Osprey, with some of the leading family-friendly attractions including Siesta Key Beach, Venice Beach and Mote Marine Laboratory & Aquarium.
Why should I book my villa holiday with Stayz?
When you select a Stayz villa rental, the only people you have to share your space with are the people you bring along. It will only be you, your loved ones and the entire place for your exclusive use. Our flexible cancellation policies also mean you can book your villa with peace of mind if your plans change.