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158 Houses

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LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$161

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

Osprey cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 14 minutes

Match: Garden

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Price per night from

$132

CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$654

Great rentals within 20 miles that match your search

University Park Country Club Property

Lakewood Ranch house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$482

Piece of Paradise

Sarasota townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Garden

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Price per night from

$109

Venice Pool Home Centrally Located, Just Waiting For You

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$276

Venice Pool Home

South Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$224

"Lido Lookout" Beach Paradise Private Home on Lido Key

Lido Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$2,983

BeautifulHome with Pool - 3 miles from Siesta Key Beach

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 38 minutes

Match: Garden

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Price per night from

$241

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$345

Dream villa in a quiet location with private pool, private beach and Wi-Fi

South Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$345

Beautiful house for rent at siesta key beach with pool, theater and game room

Siesta Key house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 15

Responds fast! avg. 2 hours 0 minutes

Match: Garden

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Price per night from

$2,856

Almost Heaven

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$287

Beautiful Florida Home

Venice house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$249

Hidden gem close to everything

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 14 minutes

Match: Garden

All filters match

Price per night from

$217

Oceanfront home

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$688

Vacation Rental Boutique Suite Amsterdam Canals

Englewood private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

All filters match

Price per night from

$224

Vacation Rental Boutique Suite Bicycles

Englewood private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

All filters match

Price per night from

$247

Vacation Rental Boutique Suite The Bridge

Englewood private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

All filters match

Price per night from

$247

Vacation Rental Boutique Suite Tulip Fields

Englewood private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

All filters match

Price per night from

$247

Match: Garden

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Price per night from

$574

Match: Garden

All filters match

Price per night from

$275

Private Retreat on Siesta Dr

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 49 minutes

Match: Garden

All filters match

Price per night from

$517

5 min away from the beach

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$230

Home in Palm Aire Golfing community

North Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$294

Sarasota Vacation • 15 Minutes to Beach • Sleeps 6

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$194

Cozy Home Near Mineral Springs

Warm Mineral Springs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Garden

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Price per night from

$230

Live like a Millionaire

Fruitville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$230

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: Garden

All filters match

Price per night from

$373

Sarasota San Jose Retreat

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

All filters match

Price per night from

$164

St Armand's Private Home on Jackson Drive

Lido Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$382

3 bedroom tropical Family home with private pool.

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$286

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$172

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$172

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

All filters match

Price per night from

$172

Tropical Breeze Triple Cottages, Sleeps 16

Sarasota house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Match: Garden

All filters match

Price per night from

$683

Sea Glass Dual Cottages, Sleeps 12, Heated Pool

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Garden

All filters match

Price per night from

$402

Captains Quarters

Casey Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

All filters match

Price per night from

$155

Viewing 38 of 158
rentals in Osprey

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