Houses Osprey

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CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

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Price per night from

$655

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Dunmore

Osprey house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$218

Great rentals within 20 miles that match your search

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Rental types Private outdoor pool (heated)

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Price per night from

$1,001

Vacation Home on Coral Sands Ct. Spring Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Rental types Private outdoor pool (heated)

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Price per night from

$155

Super clean vacation Villa with Pool

North Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 1 minutes

Match: Rental types Private outdoor pool (heated)

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Price per night from

$138

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

Match: Rental types Private outdoor pool (heated)

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Price per night from

$501

Luxury accommodation in Venetia, 3 months stay

Venice house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (heated)

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Price per night from

$192

Manasota Beach Vacation Rental

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

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Price per night from

$270

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (heated)

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Price per night from

$369

Match: Rental types Private outdoor pool (heated)

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Price per night from

$150

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (heated)

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Price per night from

$286

Captiva Paradise Home close to IMG Academy & Siesta Key Beach

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

Match: Rental types Private outdoor pool (heated)

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Price per night from

$373

Seasonal Rental

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

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Price per night from

$293

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (heated)

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Price per night from

$630

Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (heated)

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Price per night from

$689

Another Day in Paradise

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 1 minutes

Match: Rental types Private outdoor pool (heated)

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Price per night from

$545

NEAR IMG ACADEMY AND SIESTA KEY BEACH PARADISE

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 9 minutes

Match: Rental types Private outdoor pool (heated)

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Price per night from

$431

Venice Pool Home Centrally Located, Just Waiting For You

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

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Price per night from

$276

Oceanfront home

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (heated)

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Price per night from

$688

Match: Rental types Private outdoor pool (heated)

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Price per night from

$574

The Hideaway: 4/2 W Heated Pool and Outdoor Spaces, 10 mins to Sarasota Beach

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (heated)

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Price per night from

$373

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Rental types Private outdoor pool (heated)

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Price per night from

$345

Match: Rental types Private outdoor pool (heated)

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Price per night from

$316

Brand new villa with heated pool for swimmers

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

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Price per night from

$190

Lovely Brandnew Pool Villa w/ Private Beach, WiFi

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

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Price per night from

$212

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

All filters match

Price per night from

$454

Paradise 3 Bedroom Pool Home Close to Siesta Key Beach and IMG Academy

Braden River house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

Match: Rental types Private outdoor pool (heated)

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Price per night from

$372

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated)

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Price per night from

$232

Paradise 4 Bedroom Pool Home Close to Siesta Key Beach and IMG Academy

North Sarasota house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

Match: Rental types Private outdoor pool (heated)

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Price per night from

$430

Match: Rental types Private outdoor pool (heated)

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Price per night from

$171

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Rental types Private outdoor pool (heated)

All filters match

Price per night from

$716

Mid Century Home With Private Heated Pool

Tallevast house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (heated)

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Price per night from

$182

Stunning & Bright Sarasota Home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

All filters match

Price per night from

$395

Remodeled 4BR Pool Home / Golf View/Near Beaches

South Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Rental types Private outdoor pool (heated)

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Price per night from

$515

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Location location” Great house convincent , clean , close to everything

Match: Rental types Private outdoor pool (heated)

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Price per night from

$121

Heated pool home near Siesta Key

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

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Price per night from

$262

Craig House with Heated Pool

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

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Price per night from

$205

THE LIDO RESIDENCE

Lido Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Rental types Private outdoor pool (heated)

All filters match

Price per night from

$778

Viewing 38 of 83
rentals in Osprey

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