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Holiday Rentals in Osprey

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0+ rooms, 2+ guests
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₹ 1,000+
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84 rentals in Osprey.
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Dunmore
3 bedrooms
2 bathrooms
Sleeps 6
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Fisherman's Cove -A207-Full Gulf front!
1 bedroom
1 bathroom
Sleeps 4
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LUX VILLAs close to sparkling Siesta Key Beach.
2 bedrooms
2 bathrooms
Sleeps 6
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1 other traveller has booked this property
Pet friendly paradise with heated pool close to Sarasota-Osprey-Nokomis-Venice
3 bedrooms
2 bathrooms
Sleeps 5
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Sunny 3BR Oasis w/ New Appliances & Furnishings—Near Coast, Dining
3 bedrooms
2 bathrooms
Sleeps 6
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2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key
2 bedrooms
2 bathrooms
Sleeps 4
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PIRATE'S TREASURE WATERFRONT HOUSEBOAT/TINY HOUSE/FLOATING HOME
1 bedroom
1 bathroom
Sleeps 7
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Sarasota Condo w/Deck - 1/2 mile to Turtle Beach!
2 bedrooms
1 bathroom
Sleeps 4
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STRANDNAHE, EXKLUSIVE VILLA, PRIVATER POOL, RUHIGE SEELAGE
3 bedrooms
2 bathrooms
Sleeps 6
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STRANDNAHE, EXKLUSIVE VILLA, PRIVATER POOL, RUHIGE SEELAGE
3 bedrooms
2 bathrooms
Sleeps 6
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South Sarasota Home 5.3 Miles From Siesta Key
2 bedrooms
3 bathrooms
Sleeps 8
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CKBH (Casey Key Beach House)
3 bedrooms
3 bathrooms
Sleeps 6
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1 other traveller has booked this property
Siesta Heron 1 / Antigua
1 bedroom
1 bathroom
Sleeps 4
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1 other traveller has booked this property
Summerside Condo
2 bedrooms
2 bathrooms
Sleeps 6
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Gulf Gate, Saltwater Heated Pool Home, Updated and stunning!, Lanai with TV & BB
3 bedrooms
2 bathrooms
Sleeps 10
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Private Beach, Private Access, Incredible Ocean/Beach Views Throughout, WiFi/Cab
2 bedrooms
2 bathrooms
Sleeps 4
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On the sands of Turtle Beach, Updated, WiFi, Heated Indoor/Outdoor Pool, Gulf &
2 bedrooms
2 bathrooms
Sleeps 4
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Siesta Heron 6 / Sunset
2 bedrooms
2 bathrooms
Sleeps 6
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Portland
3 bedrooms
2 bathrooms
Sleeps 6
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Newly Listed Large Pool Home, WiFi/Cable, One Level, Dog with Prior Approval, Qu
3 bedrooms
2 bathrooms
Sleeps 6
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Canopy Cottage of Sarasota
2 bedrooms
2 bathrooms
Sleeps 6
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Gorgeous Bay Views, Renovated, 5 minute walk to Turtle Beach, Heated Pool on Bay
2 bedrooms
2 bathrooms
Sleeps 4
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BIG HOUSE 5br/2bth/Playground walk DOWNTOWN,Beach
5 bedrooms
2 bathrooms
Sleeps 10
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Gulf Gate Estates
4 bedrooms
2 bathrooms
Sleeps 8
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Destination Paradise - We are open for reservations!
2 bedrooms
2 bathrooms
Sleeps 4
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Private Golf Prof Design, Clay Tennis, One Level Condo, Heated Pools/Spa, Clubho
2 bedrooms
2 bathrooms
Sleeps 6
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Holiday House 4
2 bedrooms
2 bathrooms
Sleeps 6
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3bedrooms2baths,cozy Home 5 Miles From Siesta Key Beach
3 bedrooms
2 bathrooms
Sleeps 6
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Holiday House 3
1 bedroom
2 bathrooms
Sleeps 6
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Private Golf/Tennis, 2/2 Gated Condo, 5 Pools, Clubhouse, Restaurant, Full Use o
2 bedrooms
2 bathrooms
Sleeps 4
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Siesta Heron 7 / Heron House
3 bedrooms
2 bathrooms
Sleeps 8
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Siesta Heron 4 / Sand Dollar
1 bedroom
1 bathroom
Sleeps 4
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Siesta Heron 5 / Key Lime
2 bedrooms
2 bathrooms
Sleeps 6
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SMALL STUDIO APT, PERFECT LOCATION CLOSE EVERYWHERE,SIESTA (8 min), pet friendly
0 bedrooms
1 bathroom
Sleeps 2
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Siesta Heron 2 / Bahama
1 bedroom
1 bathroom
Sleeps 4
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Siesta Heron 3 / Captiva
1 bedroom
1 bathroom
Sleeps 4
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COMFY STUDIO, PERFECT LOCATION. SIESTA Key(5-10min), close everywhere
0 bedrooms
1 bathroom
Sleeps 2
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Great South Sarasota Locale, Heated Pool/Spa, Tennis, Private Laundry
2 bedrooms
2 bathrooms
Sleeps 4
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One Ocean - B
2 bedrooms
1 bathroom
Sleeps 6
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One Ocean - A
2 bedrooms
1 bathroom
Sleeps 6
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Holiday House 2
1 bedroom
1 bathroom
Sleeps 4
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Riverfront house w/ private pool, dock, & lanai - dogs welcome!
2 bedrooms
2 bathrooms
Sleeps 4
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Hamptons Escape
3 bedrooms
2 bathrooms
Sleeps 6
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Tiny House - Margarita
2 bedrooms
1 bathroom
Sleeps 6
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FLOATING HOUSE/HOUSEBOAT
2 bedrooms
2 bathrooms
Sleeps 5
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Tiny House - Blue Lifeguard Stand
2 bedrooms
1 bathroom
Sleeps 4
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Tiny House - Flamingo
1 bedroom
1 bathroom
Sleeps 3
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South Gate Ridge Holiday Home Sleeps 6 with Air Con and WiFi - 5790671
3 bedrooms
2 bathrooms
Sleeps 6
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Tiny House - The Siesta
1 bedroom
1 bathroom
Sleeps 2
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Tiny House - Sea Turtle
1 bedroom
1 bathroom
Sleeps 6
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