Osprey Vacation Rentals
Large selection of Osprey Vacation Rentals, book your property Direct and Save!
Many rental properties to choose from, including private Homes, Cottages or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities that will make your Florida visit the perfect getaway.
Newly Remodeled Palm Villa
Osprey Apartment
Enjoy memorable sunsets, with a private view and revel in all the local charm and activities the Casey Key area have to offer. Our villa has the perfect balance of ambiance and enjoyment you are looking for in your vacation to the Sarasota/Venice area. Only 7 miles from the #1 rated beach in America, Siesta Key Beach and 2 miles from the nearest b.......read more
2 Bedrooms
- Sleeps 5
Apartment in Osprey
5 star upscale 1 bed condo near Siesta Key Beach!
Osprey Condo
Stay in a beautiful mini condo on the Oaks golf course and country club in Osprey that is super close to Siesta Key beach with 1 private bedroom and king bed. New mini kitchen with stovetop, oven, and microwave. Also, a dining area, and walk-out balcony. Also, we have comfortable sofa bed. Condo is a second floor unit accessible by elevator or stai.......read more
1 Bedrooms
- Sleeps 4
Condo in Osprey
Elegant 3-Bed condo with intracoastal views
Osprey Condo
Enjoy the gorgeous amber sunsets from your expansive balcony offering panoramic views of the Intracoastal Waterway and the Gulf of Mexico! This condo is minutes away from Siesta Key Beach and downtown Sarasota. Come enjoy all Florida has to offer!
Warning!!!⚠️
$500 refundable security deposit will be required for all reservatio.......read more
3 Bedrooms
- Sleeps 4
Condo in Osprey
70-Foot Houseboat, Secluded Beach, Onsite Bikes & Golf carts to tour the Key!
Osprey Vacation Rental 
3.7 Star Review
70 foot houseboat featuring two bedrooms and two bathrooms. Living room and dining room spacious with a pull out sleeper sofa to accommodate two additional guests on a queen-size bed. Really large upper observatory deck as well as a front porch. Fully self-contained kitchen with stove oven refrigerator coffee pot toaster and many more amenities. Al.......read more
2 Bedrooms
- Sleeps 8
Vacation Rental Home in Osprey
Private Houseboat, Waterfront, Pool, Incredible fishing, Come Relax!
Osprey House boat 4.6 Star Review
NO Comparison to this.... houseboat for rent at your own private docking on the bay with Gulf access. Fully contained two bedroom with all amenities even duct in air conditioning and two bathrooms! Come experience a liveaboard opportunity. Available also for rent on site are jet skis, kayaks, paddle boards, pontoon and bikes. Additionally a golf c.......read more
2 Bedrooms
- Sleeps 6
House boat in Osprey