Osprey Villas, Cabins & more


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Areas near Osprey

1 / 17

Welcome to the Paradise

  • 3
  • 8
  • 90 nights min

$170

Details

1 / 8

Private Surf Cottage Studio with Full Kitchen- 3 Miles to Siesta Key

  • 1
  • 2
  • Min stay varies

$85

Details

1 / 4

Furnished Trailer Near Siesta Key

  • 2
  • 4
  • 30 nights min

$43

Details

1 / 29

LUX VILLAs close to sparkling Siesta Key Beach.

  • 2
  • 6
  • 1 night min

$120

Details

Great rentals within 20 miles that match your search

1 / 23

Morgan Properties - 1850 Roland -Renovated 4 Bed/3 Bath Home-Close to Siesta Key

  • 4
  • 8
  • Min stay varies

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Details

1 / 9

Remodeled Bay Tree Club Siesta Key Vacation Rental

  • 2
  • 4
  • 14 nights min

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Details

1 / 15

Newly Listed 2BR/BA. Mins to IMG Aceademy/Anna Maria Beaches and Sarasota

  • 2
  • 4
  • Min stay varies

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Details

1 / 18

Stay on Siesta, Island Reef, Panoramic Gulf Views

  • 2
  • 6
  • 30 nights min

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Details

1 / 7

Stay on Siesta - Beach House Bungalows 2

  • 2
  • 5
  • 2 nights min

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Details

1 / 23

1 Bedroom Rental in Sun N Fun Resort

  • 1
  • 4
  • 2 nights min

$178

Details

1 / 8

Casey Key Deluxe Suite with a Beachview - Unit 23

  • 1
  • 4
  • 1 night min

$198

Details

1 / 22

Siesta Key to a Great Getaway

  • 4
  • 8
  • 4 nights min

$283

Details

1 / 20

Sea Shell Cottage

  • 2
  • 6
  • Min stay varies

$145

Details

1 / 21

PRICE REDUCED AUGUST 5-19 - CALL OR EMAIL TODAY!

  • 2
  • 6
  • 7 nights min

$163

Details

1 / 16

Villa 7

  • 2
  • 6
  • Min stay varies

$167

Details

1 / 24

Affordable Ground Floor Siesta Key Vacation Rental with Heated Pool Access

  • 2
  • 6
  • Min stay varies

$93

Details

1 / 29

Beachy Villa, Pool, Bikes & Kayaks

  • 3
  • 7
  • Min stay varies

$125

Details

1 / 17

Villa 2

  • 2
  • 4
  • Min stay varies

$167

Details

1 / 13

Vacation Rental In Sarasota Florida

  • 1
  • 4
  • 7 nights min

$66

Details

1 / 20

Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front

  • 2
  • 6
  • 7 nights min

$220

Details

1 / 12

Vacation Pool Home near Shamrock and Beaches

  • 2
  • 4
  • Min stay varies

$93

Details

1 / 9

New 2017 Siesta Key 1 Bedroom King Adult only resort Villa 3

  • 1
  • 2
  • Min stay varies

$138

Details

1 / 24

Location, Location 10 Minute Walk to Beach, Heated Pool

  • 3
  • 8
  • Min stay varies

$254

Details

1 / 6

Condo overlooking intercoastel, Harbor Towers

  • 1
  • 4
  • 14 nights min

$135

Details

1 / 15

Townhouse in San Michele in Sarasota

  • 3
  • 3
  • 30 nights min

$100

Details

1 / 32

Siesta Sandcastle 353 Calle Miramar 941.349.5500

  • 3
  • 8
  • Min stay varies

$497

Details

1 / 8

Addy's Villas

  • 2
  • 6
  • 7 nights min

$134

Details

1 / 23

Full of light, quiet, spa-like

  • 3
  • 6
  • 4 nights min

$100

Details

1 / 32

Downtown Condo Sunset Dr Bay, Bridge, 10th floor

  • 1
  • 2
  • 90 nights min

$80

Details

1 / 7

Sunny Siesta Key

  • 2
  • 4
  • 14 nights min

$85

Details

1 / 15

12 South

  • 2
  • 4
  • Min stay varies

$216

Details

1 / 27
1 / 9

Beautiful location on Siesta Key

  • 3
  • 6
  • 90 nights min

$73

Details

1 / 29

Outrigger Resort unit #3

  • 3
  • 8
  • 7 nights min

$213

Details

1 / 24

Morgan Properties - Crescent Arms #703N - Updated 2 bed / 2 bath Gulf view

  • 2
  • 6
  • Min stay varies

$185

Details

1 / 14

modern townhome next to Benderson Park

  • 3
  • 6
  • 2 nights min

$199

Details

1 / 27

Ebb Tide 8 Siesta Certificate of Excellance 1 Bdr with 2 Bath

  • 1
  • 4
  • Min stay varies

$100

Details

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