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Osprey
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Apartments and Vacation Rentals in Osprey, FL
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Florida (FL)
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Air Conditioning (34)
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Kid friendly (31)
Pet friendly (16)
Elder access (5)
Smoking allowed (2)
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Condominium/Apartment (14)
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Waterfront (9)
Boat Available (2)
Water Views (1)
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35 rentals
in Osprey.
Mid-century Waterfront Home with heated pool
34 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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WATERFRONT Luxury Home! Private Pool, Dock, Close to Beaches
29 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Pet Friendly Paradise Close To Sarasota-Venice
42 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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Gorgeous Updated Heated Saltwater Pool Home, WiFi, Dog Friendly, Kayak Launch
8 reviews
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
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Quiet 2/2 condo with amazing views of Sarasota Bay from our fishing pier
5 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Paradise with a pool, pier and private beach area
2 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
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!BEACH IS CALLING YOU!! NEW LISTING!!SARASOTA/OSPREY-JUST 8 MINUTES TO BEACH
3 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key
1 review
Rental Home
2 bedrooms
1 bathroom
Sleeps 2
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CKBH (Casey Key Beach House)
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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LUX VILLAs close to sparkling Siesta Key Beach.
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Dunmore
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Casey Key Paradise
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
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Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Mimosa Sunrise - a Tropical 2 Bedroom/2 Bath House with Pool
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi
2 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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New Custom Smart Home Sarasota Family Getaway
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Private Peaceful Secluded Resort with Private beach Pools Tennis Boat dock
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Phoenix Retreat - Relaxing 3 bedroom home away from home
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Remodeled Waterfront Cottage
Rental Home
2 bedrooms
1 bathroom
Sleeps 2
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2 bedroom condo in osprey
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 6
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Gulf breezes in 2 bedroom tropical oasis - 10 min from beach!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Cozy and Peaceful Condo *King Bed*
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Pool, Hot tub, Close to Beaches, Shopping, More!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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RELAX. ENJOY.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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5 star upscale 1 bed condo near Siesta Key Beach!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Renovated Waterfront Home
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Luxury Condo on the water with Intercostal view
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Welcome to Lime on Green
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
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14 Minutes from Siesta Key Beaches!
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Newly Remodeled Palm Villa
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Astonishing Sarasota vacation home (New house)
Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
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Peaceful Patch of Paradise w Proximity to Plenty
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Comfortable Private Master Suite in pet/smoke free house share with prof. fem.
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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2bd/2ba Condo, Pool, Gym, Pickleball, Tennis, walk to Gulf, restaurants, shop
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Stoneybrook Golf & Country Club
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Showing results 1-35 of 35
Frequently Asked Questions about Osprey
Do any vacation rentals in Osprey have a pool?
Yes, here are some popular vacation rentals in Osprey that have a pool:
LUX VILLAs close to sparkling Siesta Key Beach.
CKBH (Casey Key Beach House)
Private Peaceful Secluded Resort with Private beach Pools Tennis Boat dock
See all vacation rentals with a pool in Osprey on Tripadvisor
Do any vacation rentals in Osprey have internet access?
Yes, here are some popular vacation rentals in Osprey that have internet access:
Dunmore
LUX VILLAs close to sparkling Siesta Key Beach.
Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key
See all vacation rentals in Osprey on Tripadvisor
What are the best pet friendly rentals in Osprey?
The best pet friendly rentals in Osprey are:
Dunmore
LUX VILLAs close to sparkling Siesta Key Beach.
Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key
See all pet friendly vacation rentals in Osprey on Tripadvisor
What are some great rentals in Osprey that are kid friendly?
Some of the most popular kid friendly rentals in Osprey are:
Dunmore
LUX VILLAs close to sparkling Siesta Key Beach.
Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi
See all kid friendly vacation rentals in Osprey on Tripadvisor