Osprey Holiday Apartments
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36 rentals in Osprey.
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Welcome To Our 2B/2B Beach Getaway That Is A Home Away From Home!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mid-century Waterfront Home with heated pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Idyllic Casey Key Beach House
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Fisherman's Cove A114 - The Havana
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Fisherman's Cove B102 - The Kingston - Private Gulf Front Beach is Open!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pet Friendly Paradise With Heated Pool Close To Sarasota-Osprey-Nokomis-Venice
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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TINY HOUSE WATERFRONT, KAYAK, GOLF CART, FISHING, BEACH, PRIVATE HOUSEBOAT POOL
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Spacious Waterfront Retreat
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Condo 2 Bedrooms, 2 Baths Between Sarasota and Venice
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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WATERFRONT, PRIVATE, BEST FISH, HOUSE BOAT, PADDLEBOARD, KAYAK, SCULLING, BEACH
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Rare beachfront estate private property
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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HOUSEBOAT, 2 BEDROOMS CASEY KEY, TINY HOUSE, BEACH, POOL, WATERFRONT
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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WATERFRONT, BEACH, POOL, UNIQUE PRIVATE SPACE, HOUSEBOAT, FISH, KAYAKS
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 11
Match: Sleeps
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New Listing !! Amazing Beachfront Condo - Siesta Key, FL -
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunrise Cove - Siesta Key Large 3 BR/2 BA, Beautiful Water Views and Beach
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Executive Listing. Heated Pool, Dog Friendly, Kayak Launch & Park, Private S
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Private Guest House Close To Beach
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BEAUTIFULL VACATION HOUSE
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bay Front Spacious Bright 3 Bdrm/4 Bath Condo. Turtle Beach/Siesta Key
Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Convenient Cottage Close to Beaches and Pet Friendly
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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'THE BIG HOUSE' HOUSEBOAT, OUTDOOR LIVING GALORE!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Location. Beautiful Waterviews. Heated Pool. 2 BD/2 BA
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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PIRATE'S TREASURE WATERFRONT HOUSEBOAT/TINY HOUSE/FLOATING HOME
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
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WATERFRONT SARASOTA COUNTY, CASEY KEY. 5 MILES TO SIESTA KEY BEACH. POOL HOT TUB
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 11
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70 feet of WATERFTONT BLISS! HOUSEBOAT
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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CKBH (Casey Key Beach House)
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Million Dollar View of Bay Sunrises and Gulf Sunsets-See the Video
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
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LUX VILLAs close to sparkling Siesta Key Beach.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Listing! Steps to Bay & Fishing Pier, Splash Pool, WiFi, Separate Casita, Tw
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mimosa Sunrise - a Tropical 2 Bedroom/2 Bath House with Pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dunmore
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous Updated Heated Saltwater Pool Home, WiFi, Dog Friendly, Kayak Launch &
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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Phoenix Retreat - Relaxing 3 bedroom home away from home
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant 3-Bed condo with intracoastal views
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Frequently Asked Questions about Osprey
- Yes, here are some popular holiday rentals in Osprey that have a pool:\n
- \n
- New Listing !! Amazing Beachfront Condo - Siesta Key, FL - \n
- LUX VILLAs close to sparkling Siesta Key Beach. \n
- CKBH (Casey Key Beach House) \n
- Yes, here are some popular holiday rentals in Osprey that have internet access:\n
- \n
- New Listing !! Amazing Beachfront Condo - Siesta Key, FL - \n
- LUX VILLAs close to sparkling Siesta Key Beach. \n
- CKBH (Casey Key Beach House) \n
- The best pet friendly rentals in Osprey are:\n\nSee all pet friendly holiday rentals in Osprey on Tripadvisor
- Some of the most popular kid friendly rentals in Osprey are:\n
- \n
- New Listing !! Amazing Beachfront Condo - Siesta Key, FL - \n
- LUX VILLAs close to sparkling Siesta Key Beach. \n
- CKBH (Casey Key Beach House) \n