Osprey villas
We found 401 villas — enter your dates for availability
Explore Osprey villa rentals
Paradise with a pool, pier and private beach area
Sleeps 12 · 5 bedrooms · 3+ bathrooms
9.09.0 out of 10
Wonderfulwonderful
18 reviews(18 reviews)
NEW - Cheerful 2 bedroom villa - 13 min. to Siesta Key
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Serene Villa in Resort-like Community 10 minutes to Award winning Siesta Key
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Venice Island / Venice Beach Luxury Villa
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
114 reviews(114 reviews)
Walk to Nokomis Beach. Quality, Cleanliness, Affordable. SmartTV, Full Kitchen
Sleeps 4 · 2 bedrooms · 1 bathroom
8.68.6 out of 10
Excellentexcellent
74 reviews(74 reviews)
Huge Beach Villa, Mins To Beach With Private Salt Water Heated Pool
Sleeps 6 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Top rated villa rentals - Osprey
Everything excellent
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Fantastic stay
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Great beach location
1010 out of 10
Exceptionalexceptional
137 reviews(137 reviews)
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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, Vrbo 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 (57ºF) and 20ºC (68ºF), 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 Vrbo 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 Vrbo’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 Vrbo?
Booking a villa rental with Vrbo means you’ll have the whole place for your exclusive use — your own private oasis, without any distractions from anybody else. Also, our flexible payment and cancellation policies give you the freedom to alter your plans if necessary. What’s more, our One Key™ rewards programme lets you collect and spend OneKeyCash™* on all eligible bookings with Vrbo. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.