Osprey Villas, Cabins & more


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Areas near Osprey

Great rentals within 20 miles that match your search

1 / 33

Tropical Escape 1 Br Siesta Key Inn

  • 1
  • 4
  • 5 nights min

$200

Details

1 / 24

Topsail Cottage

  • 4
  • 12
  • Min stay varies

$346

Details

1 / 25

Pet Friendly Condo with Gulf Views

  • 2
  • 6
  • 2 nights min

$120

Details

1 / 35

Villa Trinidad

  • 4
  • 10
  • Min stay varies

$193

Details

1 / 16

Venice beach island getaway

  • 2
  • 4
  • Min stay varies

$61

Details

1 / 6

1670 Laurel St

  • 2
  • 4
  • 7 nights min

$109

Details

1 / 37

Tara Golf and Country Club

  • 4
  • 10
  • 7 nights min

$191

Details

1 / 30

Casita Sol

  • 2
  • 4
  • Min stay varies

$146

Details

1 / 25

The Water's Edge

  • 2
  • 6
  • Min stay varies

$90

Details

1 / 34

Venice Island on BEACH 8th flr near Siesta Key

  • 2
  • 5
  • 90 nights min

$147

Details

1 / 27

Beautiful 2BA/2BR Condo. Mins to IMG/Beaches/Dining.

  • 2
  • 4
  • Min stay varies

$114

Details

1 / 24

Morgan Properties - Palm Bay Club #312 Bay Side - Renovated 2 Bedroom/2 Bath

  • 2
  • 4
  • Min stay varies

$150

Details

1 / 24

Morgan Properties-Crystal Sands Villa 22-100% Renovated 2 Bed/2 Bath Close Beach

  • 2
  • 4
  • Min stay varies

$129

Details

1 / 27

Beautiful gated community near Siesta Key beach and downtown Sarasota

  • 2
  • 4
  • 5 nights min

$59

Details

1 / 10

Walk to beach & St Armand's Circle !!!

  • 1
  • 2
  • Min stay varies

$100

Details

1 / 22

Upscale 4 Bed Private Heated Pool Home spa.

  • 4
  • 9
  • 4 nights min

$196

Details

1 / 21

Villa Brisa Marina

  • 4
  • 12
  • Min stay varies

Inquire for Rates

Details

1 / 17

Villa 2

  • 2
  • 4
  • Min stay varies

$169

Details

1 / 18

Light and Airy and Private, Great Location

  • 1
  • 3
  • 4 nights min

$150

Details

1 / 26

Siesta Key Unit #4

  • 1
  • 4
  • 3 nights min

$100

Details

1 / 33

Vacation Home with Private Beach ! Summer Special !!!

  • 3
  • 5
  • Min stay varies

$90

Details

1 / 55

Downtown Sarasota five star home

  • 3
  • 6
  • Min stay varies

$154

Details

1 / 24

Paradise Villa: Spacious Grounds & Private Pool

  • 2
  • 6
  • 30 nights min

$172

Details

1 / 18

Timberwoods Vacation Villa Best Value in Sarasota

  • 2
  • 6
  • 7 nights min

$75

Details

1 / 27

Elegant 2BA/2BR Condo. Mins from IMG/Beaches/Shops

  • 2
  • 4
  • Min stay varies

$113

Details

1 / 12

Luxurious 5 Bed / 3 Bath home with private pool

  • 5
  • 10
  • 7 nights min

$235

Details

1 / 41

A Tropical 2Br Retreat on a Florida Isle

  • 2
  • 5
  • 7 nights min

$269

Details

1 / 42

Piece of Paradise by Siesta Beach

  • 3
  • 6
  • 7 nights min

$239

Details

1 / 21

AAA Accommodation in The Meadows - Sarasota

  • 2
  • 6
  • Min stay varies

$86

Details

1 / 35

Old house

  • 4
  • 8
  • Min stay varies

$156

Details

1 / 18

Venice, Florida

  • 4
  • 8
  • 30 nights min

$90

Details

1 / 8

Vacation House close to Warm Mineral spring and Florida Beaches

  • 1
  • 2
  • 7 nights min

$60

Details

1 / 27

BeachWalk Beachwalk Unit B

  • 3
  • 8
  • 7 nights min

$169

Details

1 / 4

Furnished Trailer Near Siesta Key

  • 2
  • 4
  • 30 nights min

$43

Details

1 / 17

Welcome to the Paradise

  • 3
  • 8
  • 90 nights min

$171

Details

1 / 29

LUX VILLAs close to sparkling Siesta Key Beach.

  • 2
  • 6
  • 1 night min

$120

Details

1 / 8

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

  • 1
  • 2
  • Min stay varies

$85

Details

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