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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
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Mid-century Waterfront Home with heated pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Idyllic Casey Key Beach House, holiday rental in Osprey
Idyllic Casey Key Beach House, holiday rental in Osprey
Idyllic Casey Key Beach House, holiday rental in Osprey

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, holiday rental in Osprey
Fisherman's Cove  A114 - The Havana, holiday rental in Osprey
Fisherman's Cove  A114 - The Havana, holiday rental in Osprey

Fisherman's Cove A114 - The Havana

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fisherman's Cove  B102 - The Kingston - Private Gulf Front Beach is Open!, holiday rental in Osprey
Fisherman's Cove  B102 - The Kingston - Private Gulf Front Beach is Open!, holiday rental in Osprey
Fisherman's Cove  B102 - The Kingston - Private Gulf Front Beach is Open!, holiday rental in Osprey

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 in Osprey
Pet Friendly Paradise With Heated Pool Close To Sarasota-Osprey-Nokomis-Venice, holiday rental in Osprey
Pet Friendly Paradise With Heated Pool Close To Sarasota-Osprey-Nokomis-Venice, holiday rental in Osprey

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 in Osprey
TINY HOUSE WATERFRONT, KAYAK, GOLF CART, FISHING, BEACH, PRIVATE HOUSEBOAT POOL, holiday rental in Osprey
TINY HOUSE WATERFRONT, KAYAK, GOLF CART, FISHING, BEACH, PRIVATE HOUSEBOAT POOL, holiday rental in Osprey

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 in Osprey
Spacious Waterfront Retreat, holiday rental in Osprey
Spacious Waterfront Retreat, holiday rental in Osprey

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, holiday rental in Osprey
Waterfront Condo 2 Bedrooms, 2 Baths Between Sarasota and Venice, holiday rental in Osprey
Waterfront Condo 2 Bedrooms, 2 Baths Between Sarasota and Venice, holiday rental in Osprey

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 in Osprey
WATERFRONT, PRIVATE, BEST FISH, HOUSE BOAT, PADDLEBOARD, KAYAK, SCULLING, BEACH, holiday rental in Osprey
WATERFRONT, PRIVATE, BEST FISH, HOUSE BOAT, PADDLEBOARD, KAYAK, SCULLING, BEACH, holiday rental in Osprey

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 in Osprey
Rare beachfront estate private property, holiday rental in Osprey
Rare beachfront estate private property, holiday rental in Osprey

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 in Osprey
HOUSEBOAT, 2 BEDROOMS CASEY KEY, TINY HOUSE, BEACH, POOL, WATERFRONT, holiday rental in Osprey
HOUSEBOAT, 2 BEDROOMS CASEY KEY, TINY HOUSE, BEACH, POOL, WATERFRONT, holiday rental in Osprey

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 in Osprey
WATERFRONT, BEACH, POOL, UNIQUE PRIVATE SPACE, HOUSEBOAT, FISH, KAYAKS, holiday rental in Osprey
WATERFRONT, BEACH, POOL, UNIQUE PRIVATE SPACE, HOUSEBOAT, FISH, KAYAKS, holiday rental in Osprey

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 -, holiday rental in Osprey
New Listing !! Amazing Beachfront Condo - Siesta Key, FL -, holiday rental in Osprey
New Listing !! Amazing Beachfront Condo - Siesta Key, FL -, holiday rental in Osprey

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 in Osprey
New Executive Listing. Heated Pool, Dog Friendly, Kayak Launch & Park, Private S, holiday rental in Osprey
New Executive Listing. Heated Pool, Dog Friendly, Kayak Launch & Park, Private S, holiday rental in Osprey

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 in Osprey
Private Guest House Close To Beach, holiday rental in Osprey
Private Guest House Close To Beach, holiday rental in Osprey

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 in Osprey
BEAUTIFULL VACATION HOUSE, holiday rental in Osprey
BEAUTIFULL VACATION HOUSE, holiday rental in Osprey

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, holiday rental in Osprey
Bay Front Spacious Bright 3 Bdrm/4 Bath Condo. Turtle Beach/Siesta Key, holiday rental in Osprey
Bay Front Spacious Bright 3 Bdrm/4 Bath Condo. Turtle Beach/Siesta Key, holiday rental in Osprey

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 in Osprey
Convenient Cottage Close to Beaches and Pet Friendly, holiday rental in Osprey
Convenient Cottage Close to Beaches and Pet Friendly, holiday rental in Osprey

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 in Osprey
'THE BIG HOUSE' HOUSEBOAT, OUTDOOR LIVING GALORE!, holiday rental in Osprey
'THE BIG HOUSE' HOUSEBOAT, OUTDOOR LIVING GALORE!, holiday rental in Osprey

'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, holiday rental in Osprey
Perfect Location. Beautiful Waterviews. Heated Pool. 2 BD/2 BA, holiday rental in Osprey
Perfect Location. Beautiful Waterviews. Heated Pool. 2 BD/2 BA, holiday rental in Osprey

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 in Osprey
PIRATE'S TREASURE WATERFRONT HOUSEBOAT/TINY HOUSE/FLOATING HOME, holiday rental in Osprey
PIRATE'S TREASURE WATERFRONT HOUSEBOAT/TINY HOUSE/FLOATING HOME, holiday rental in Osprey

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 in Osprey
WATERFRONT SARASOTA COUNTY, CASEY KEY. 5 MILES TO SIESTA KEY BEACH. POOL HOT TUB, holiday rental in Osprey
WATERFRONT SARASOTA COUNTY, CASEY KEY. 5 MILES TO SIESTA KEY BEACH. POOL HOT TUB, holiday rental in Osprey

WATERFRONT SARASOTA COUNTY, CASEY KEY. 5 MILES TO SIESTA KEY BEACH. POOL HOT TUB

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 11
Match: Sleeps
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70 feet of WATERFTONT BLISS! HOUSEBOAT, holiday rental in Osprey
70 feet of WATERFTONT BLISS! HOUSEBOAT, holiday rental in Osprey
70 feet of WATERFTONT BLISS! HOUSEBOAT, holiday rental in Osprey

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 in Osprey
CKBH (Casey Key Beach House), holiday rental in Osprey
CKBH (Casey Key Beach House), holiday rental in Osprey

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, holiday rental in Osprey
Million Dollar View of Bay Sunrises and Gulf Sunsets-See the Video, holiday rental in Osprey
Million Dollar View of Bay Sunrises and Gulf Sunsets-See the Video, holiday rental in Osprey

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 in Osprey
Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key , holiday rental in Osprey
Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key , holiday rental in Osprey

Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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LUX VILLAs close to sparkling Siesta Key Beach., holiday rental in Osprey
LUX VILLAs close to sparkling Siesta Key Beach., holiday rental in Osprey
LUX VILLAs close to sparkling Siesta Key Beach., holiday rental in Osprey

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 in Osprey
New Listing! Steps to Bay & Fishing Pier, Splash Pool, WiFi, Separate Casita, Tw, holiday rental in Osprey
New Listing! Steps to Bay & Fishing Pier, Splash Pool, WiFi, Separate Casita, Tw, holiday rental in Osprey

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, holiday rental in Osprey
Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key, holiday rental in Osprey
Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key, holiday rental in Osprey

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 in Osprey
Mimosa Sunrise - a Tropical 2 Bedroom/2 Bath House with Pool, holiday rental in Osprey
Mimosa Sunrise - a Tropical 2 Bedroom/2 Bath House with Pool, holiday rental in Osprey

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 in Osprey
Dunmore, holiday rental in Osprey
Dunmore, holiday rental in Osprey

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 in Osprey
Gorgeous Updated Heated Saltwater  Pool Home, WiFi, Dog Friendly, Kayak Launch &, holiday rental in Osprey
Gorgeous Updated Heated Saltwater  Pool Home, WiFi, Dog Friendly, Kayak Launch &, holiday rental in Osprey

Gorgeous Updated Heated Saltwater Pool Home, WiFi, Dog Friendly, Kayak Launch &

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Phoenix Retreat - Relaxing 3 bedroom home away from home, holiday rental in Osprey
Phoenix Retreat - Relaxing 3 bedroom home away from home, holiday rental in Osprey
Phoenix Retreat - Relaxing 3 bedroom home away from home, holiday rental in Osprey

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, holiday rental in Osprey
Elegant 3-Bed condo with intracoastal views, holiday rental in Osprey
Elegant 3-Bed condo with intracoastal views, holiday rental in Osprey

Elegant 3-Bed condo with intracoastal views

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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