Osprey vacation rentals
We found 6,720 vacation rentals — enter your dates for availability
Find the perfect place for your stay in Osprey by choosing from 31 houses, 25 condos, and other vacation rentals. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include hot tub and a washer and dryer. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.
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Bikes, Kayaks & SUP's - Sleeps ten comfortably! Your Penthouse suite is ready!
Sleeps 10 · 3 bedrooms · 2 bathrooms
Top rated rentals - Osprey
Photo gallery for Private Deck, Steps to Best Beaches and World Famous Siesta Village!
Sweet Stay in Siesta Key
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value