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Houses Longboat Key

1,373 houses

Relaxing 3 Bedroom/ 2 Bath Canal side Pool Home-"Dockside Delight"

Siesta Key house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$284

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Zilli Ocean Front 202 & Suite

Longboat Key condo

  • Nearest beach 45 mi
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$174

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • Child Friendly
  • •  Pet Friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$197

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$228

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$228

Beach View One Bedroom& Steps from the Village!!- 178

Siesta Key villa

  • Child Friendly
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$220

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$228

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$182

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$240

Cute 2Bedroom/1Bath Cottage- Across from Siesta Key Beach Access-Cottage by Sea

Siesta Key cottage

  • Child Friendly
  • •  Pet Friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$194

Stunning 2Bed/1Bath Across the Street from Siesta Key Beach!!-Pink flamingo LTD

Siesta Key apartment

  • Child Friendly
  • •  Pet Friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$228

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$182

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$160

Darling 1 Bedroom/ 1 Bath with private patio and 1 block to village!!- VH Island

Siesta Key apartment

  • Child Friendly
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$171

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$583

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$205

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$171

"Cottage by the Sea" 1 Bedroom/ 1 Bath Across From Beach!!- · 3031, 3032

Siesta Key cottage

  • Child Friendly
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$171

Cute 2 Bed/ 2 Bath just 1 block from Siesta Key Village!!-Village House, Gulf

Siesta Key apartment

  • Child Friendly
  • •  Pet Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$186

Sarasota Pinecraft Cottage 2

Sarasota cottage

  • Nearest beach 8 mi
  • •  Child Friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$149

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$205

Beachy One Bedroom Steps from Beach and Village!!! · 177 Casa Del Miramar

Siesta Key villa

  • Child Friendly
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$186

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$228

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Freezer, Rental types, Staffed property

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Price per night from

$215

Home for vacation rental in sunshine Sarasota, FL

Gulf Gate Estates house

  • Child Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Freezer, Rental types, Staffed property

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Price per night from

$117

Siesta Key Inn - Sea Gem #124

Siesta Key condo

  • Nearest beach 0.09 mi
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$232

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$169

2 Bedroom/ 2 Bath Flat Across from Public Beach Access!!-541

Siesta Key apartment

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$205

Cute Siesta Key Cottage across from beach access!!-543

Siesta Key cottage

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$205

2 Bedroom/ 1 One Bath Gem Just Steps from Siesta Key Beach!!-Barefoot Bungalow

Siesta Key cottage

  • Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$171

2 Bedroom/ 2 Bath at Palm Bay Club with Two Pools and Beach Access!!- PBC 343

Siesta Key condo

  • Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$217

Beachy One Bedroom/ One Bath Just Steps from Siesta Key Beach!!-Minorga

Siesta Key apartment

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$171

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • Car not necessary
  • •  Air conditioning
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$196

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • Nearest beach 5 mi
  • •  Air conditioning
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$99

1 Bedroom/ 1 Bath just 1 block from Siesta Key Village!!-Village House, Hibiscus

Siesta Key apartment

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$137

Luxury Oasis 2 Bedroom/ 2 Bath with Pool and Spa!!-Seven Nights 304

Siesta Key apartment

  • Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$205

2 Bed/2 Bath Renovated Bay Oaks Unit- Top Floor!!-E.35

Siesta Key apartment

  • Child Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$205

Lido Beach Villa, 1.2k sf, 1 block to the beach

Lido Key villa

  • Nearest beach 0 mi
  • •  Child Friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Freezer, Staffed property

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Price per night from

$184

Viewing 38 of 1,373
rentals in Longboat Key

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