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Osprey, FL Holiday Rentals, Apartments and Villas
Holiday Rentals
USA
Florida (FL)
Osprey, FL Holiday Rentals, Apartments and Villas
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36 rentals
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Welcome To Our 2B/2B Beach Getaway That Is A Home Away From Home!
59 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Mid-century Waterfront Home with heated pool
29 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Idyllic Casey Key Beach House
29 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Fisherman's Cove A114 - The Havana
57 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Fisherman's Cove B102 - The Kingston - Private Gulf Front Beach is Open!
38 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Pet Friendly Paradise With Heated Pool Close To Sarasota-Osprey-Nokomis-Venice
40 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
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TINY HOUSE WATERFRONT, KAYAK, GOLF CART, FISHING, BEACH, PRIVATE HOUSEBOAT POOL
37 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
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Spacious Waterfront Retreat
20 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Waterfront Condo 2 Bedrooms, 2 Baths Between Sarasota and Venice
11 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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WATERFRONT, PRIVATE, BEST FISH, HOUSE BOAT, PADDLEBOARD, KAYAK, SCULLING, BEACH
20 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
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Rare beachfront estate private property
8 reviews
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
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HOUSEBOAT, 2 BEDROOMS CASEY KEY, TINY HOUSE, BEACH, POOL, WATERFRONT
30 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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WATERFRONT, BEACH, POOL, UNIQUE PRIVATE SPACE, HOUSEBOAT, FISH, KAYAKS
17 reviews
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 11
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New Listing !! Amazing Beachfront Condo - Siesta Key, FL -
10 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Sunrise Cove - Siesta Key Large 3 BR/2 BA, Beautiful Water Views and Beach
10 reviews
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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New Executive Listing. Heated Pool, Dog Friendly, Kayak Launch & Park, Private S
7 reviews
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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Private Guest House Close To Beach
10 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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BEAUTIFULL VACATION HOUSE
8 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Bay Front Spacious Bright 3 Bdrm/4 Bath Condo. Turtle Beach/Siesta Key
11 reviews
Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
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Convenient Cottage Close to Beaches and Pet Friendly
14 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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'THE BIG HOUSE' HOUSEBOAT, OUTDOOR LIVING GALORE!
7 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Perfect Location. Beautiful Waterviews. Heated Pool. 2 BD/2 BA
1 review
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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PIRATE'S TREASURE WATERFRONT HOUSEBOAT/TINY HOUSE/FLOATING HOME
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 7
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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
11 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
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CKBH (Casey Key Beach House)
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Million Dollar View of Bay Sunrises and Gulf Sunsets-See the Video
1 review
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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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
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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
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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
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Dunmore
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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
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Elegant 3-Bed condo with intracoastal views
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 4
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1
Frequently Asked Questions about Osprey
Do any holiday rentals in Osprey have a pool?
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
\n
See all holiday rentals with a pool in Osprey on Tripadvisor
Do any holiday rentals in Osprey have internet access?
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
\n
See all holiday rentals in Osprey on Tripadvisor
What are the best pet friendly rentals in Osprey?
The best pet friendly rentals in Osprey are:\n
\n
LUX VILLAs close to sparkling Siesta Key Beach.
\n
CKBH (Casey Key Beach House)
\n
Dunmore
\n
\n
See all pet friendly holiday 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:\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
\n
See all kid friendly holiday rentals in Osprey on Tripadvisor