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Osprey Holiday Rentals

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20 rentals in Osprey.
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Welcome To Our 2B/2B Beach Getaway That Is A Home Away From Home!, holiday rental in Osprey

Welcome To Our 2B/2B Beach Getaway That Is A Home Away From Home!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mid-century Waterfront Home with heated pool, holiday rental in Osprey

Mid-century Waterfront Home with heated pool

3 bedrooms
2 bathrooms
Sleeps 8
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Spacious Waterfront Retreat, holiday rental in Osprey

Spacious Waterfront Retreat

3 bedrooms
3 bathrooms
Sleeps 6
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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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sunrise Cove - Siesta Key Large 3 BR/2 BA, Beautiful Water Views and Beach, holiday rental in Osprey

Sunrise Cove - Siesta Key Large 3 BR/2 BA, Beautiful Water Views and Beach

3 bedrooms
2 bathrooms
Sleeps 6
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Private Guest House Close To Beach, holiday rental in Osprey

Private Guest House Close To Beach

2 bedrooms
1 bathroom
Sleeps 4
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2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key, holiday rental in Osprey

2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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CKBH (Casey Key Beach House), holiday rental in Osprey

CKBH (Casey Key Beach House)

3 bedrooms
3 bathrooms
Sleeps 6
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LUX VILLAs close to sparkling Siesta Key Beach., holiday rental in Osprey

LUX VILLAs close to sparkling Siesta Key Beach.

2 bedrooms
2 bathrooms
Sleeps 6
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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

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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2Bedroom Beach Cottage - 3 Miles to Siesta Key, holiday rental in Osprey

2Bedroom Beach Cottage - 3 Miles to Siesta Key

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Sunny Oasis w/ New Appliances & Furnishings - Near Coast, Dining, holiday rental in Osprey

Sunny Oasis w/ New Appliances & Furnishings - Near Coast, Dining

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dunmore, holiday rental in Osprey

Dunmore

3 bedrooms
2 bathrooms
Sleeps 6
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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

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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2 bedroom condo in osprey, holiday rental in Osprey

2 bedroom condo in osprey

1 bedroom
2 bathrooms
Sleeps 6
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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tranquil Sarasota Home < 1 Mile to Boat Launch!, holiday rental in Osprey

Tranquil Sarasota Home < 1 Mile to Boat Launch!

3 bedrooms
2 bathrooms
Sleeps 5
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

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful Stoneybrook Golf Course Condo! Veranda Greens - Overlooks 16th green, holiday rental in Osprey

Beautiful Stoneybrook Golf Course Condo! Veranda Greens - Overlooks 16th green

2 bedrooms
2 bathrooms
Sleeps 5
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Remodeled 2 bdrm villa with boat dock, holiday rental in Osprey

Remodeled 2 bdrm villa with boat dock

2 bedrooms
2 bathrooms
Sleeps 6
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