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Osprey Vacation Rentals
1-24 of 63 rentals

Fishing on Sunshine

$327 avg / night (excludes fees and taxes)
NEW!
Osprey, FL
4 Bedrooms | 2 Bath | Sleeps 8

Bay Acres Bungalow - B

$145 avg / night (excludes fees and taxes)
NEW!
Osprey, FL
2 Bedrooms | 2 Bath | Sleeps 6

Bay Acres Bungalow

$277 avg / night (excludes fees and taxes)
NEW!
Osprey, FL
2 Bedrooms | 2 Bath | Sleeps 12

Bay Acres Bungalow - A

$147 avg / night (excludes fees and taxes)
NEW!
Osprey, FL
2 Bedrooms | 2 Bath | Sleeps 6

Villa De La Mar at Casey Key

$1,803 avg / night (excludes fees and taxes)
Nokomis, FL
4.08 (26)
5 Bedrooms | 6.5 Bath | Sleeps 12

Nokomis Nirvana

$194 avg / night (excludes fees and taxes)
Nokomis, FL
5.0 (4)
3 Bed | 2 Bath | Sleeps 5 (4 Adults Max)

Seaside

$300 avg / night (excludes fees and taxes)
NEW!
Nokomis, FL
5.0 (1)
3 Bedrooms | 3 Bath | Sleeps 8

Parrot Beach Cottages Suite #4

$260 avg / night (excludes fees and taxes)
Siesta Key, FL
4.35 (72)
1 Bed | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #2

$214 avg / night (excludes fees and taxes)
Siesta Key, FL
4.62 (86)
0 Bedrooms | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #1

$193 avg / night (excludes fees and taxes)
Siesta Key, FL
4.48 (79)
0 Bedrooms | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #3

$225 avg / night (excludes fees and taxes)
Siesta Key, FL
4.19 (77)
1 Bed | 1 Bath | Sleeps 4 (2 Adults Max)

Midnight Cove II 823

$159 avg / night (excludes fees and taxes)
Siesta Key, FL
4.45 (22)
2 Bedrooms | 1.5 Bath | Sleeps 6

The Palm Bay Club Unit 311

$238 avg / night (excludes fees and taxes)
Siesta Key, FL
4.12 (50)
2 Bedrooms | 2 Bath | Sleeps 4

Beach Road Condo Unit 2

$636 avg / night (excludes fees and taxes)
Siesta Key, FL
4.33 (6)
3 Bedrooms | 2 Bath | Sleeps 6

Sea Winds 117

$142 avg / night (excludes fees and taxes)
Siesta Key, FL
4.4 (5)
1 Bedrooms | 1 Bath | Sleeps 4

Sweet Beach Retreat

$188 avg / night (excludes fees and taxes)
NEW!
Siesta Key, FL
2 Bedrooms | 2 Bath | Sleeps 6

Turtle Bay Beauty

$121 avg / night (excludes fees and taxes)
Siesta Key, FL
4.67 (6)
2 Bedrooms | 2 Bath | Sleeps 4

Siesta Key Beach Hideaway

$417 avg / night (excludes fees and taxes)
NEW!
Siesta Key, FL
4 Bedrooms | 3 Bath | Sleeps 12

Peppertree Perfection

$108 avg / night (excludes fees and taxes)
Siesta Key, FL
4.33 (3)
2 Bedrooms | 1.5 Bath | Sleeps 4

'Sea- Esta' Winds 209

$152 avg / night (excludes fees and taxes)
Siesta Key, FL
4.73 (11)
1 Bedrooms | 1 Bath | Sleeps 4

Anything Is Possible

$348 avg / night (excludes fees and taxes)
Sarasota, FL
4.61 (38)
3 Bedrooms | 3 Bath | Sleeps 8

BoHo Bungalow

$295 avg / night (excludes fees and taxes)
NEW!
Sarasota, FL
3 Bedrooms | 2 Bath | Sleeps 6

Beach House

$231 avg / night (excludes fees and taxes)
NEW!
Sarasota, FL
3 Bedrooms | 2 Bath | Sleeps 6

The Key Escape

$175 avg / night (excludes fees and taxes)
NEW!
Sarasota, FL
2 Bedrooms | 1.5 Bath | Sleeps 4
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