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Summerland Key Vacation Rentals
1-24 of 115 rentals

Skyway Living

$333 avg / night (excludes fees and taxes)
Summerland Key, FL
5.0 (5)
2 Bedrooms | 3.5 Bath | Sleeps 6

Endless Summerland

$459 avg / night (excludes fees and taxes)
NEW!
Summerland Key, FL
3 Bedrooms | 2 Bath | Sleeps 6

Summerland Canal

$269 avg / night (excludes fees and taxes)
Summerland Key, FL
3.88 (8)
2 Bedrooms | 1 Bath | Sleeps 5

Parrotfish Point

$349 avg / night (excludes fees and taxes)
Cudjoe Key, FL
5.0 (5)
3 Bedrooms | 3 Bath | Sleeps 6

Hawkins Lookout

$391 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.4 (5)
3 Bedrooms | 2.5 Bath | Sleeps 6

The Blue Marlin

$282 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.67 (3)
2 Bedrooms | 2.5 Bath | Sleeps 6

Dock Holiday

$245 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.48 (25)
2 Bedrooms | 2 Bath | Sleeps 4

The Mermaid Manor

$447 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.0 (3)
4 Bedrooms | 4 Bath | Sleeps 10

Luxury Villa of the Setting Sun -Near Key West Fl

$2,043 avg / night (excludes fees and taxes)
Near Key West , FL
4.68 (41)
4 Bedrooms | 4.5 Bath | Sleeps 8

Salty Air Retreat

$296 avg / night (excludes fees and taxes)
NEW!
Little Torch Key, FL
3 Bedrooms | 2 Bath | Sleeps 8

Torchbearer - Lower

$142 avg / night (excludes fees and taxes)
NEW!
Little Torch Key, FL
2 Bedrooms | 1 Bath | Sleeps 6

Cayo Loco

$279 avg / night (excludes fees and taxes)
Little Torch Key, FL
4.5 (2)
3 Bedrooms | 2 Bath | Sleeps 6

Big Pine Bungalow

$326 avg / night (excludes fees and taxes)
NEW!
Big Pine Key, FL
3 Bedrooms | 2 Bath | Sleeps 7

Sunset Villa

$257 avg / night (excludes fees and taxes)
Big Pine Key, FL
4.0 (3)
3 Bedrooms | 2 Bath | Sleeps 6

Big Pine Key Dreams

$235 avg / night (excludes fees and taxes)
Big Pine Key, FL
4.83 (6)
2 Bedrooms | 2 Bath | Sleeps 6

Tradewinds Treat

$235 avg / night (excludes fees and taxes)
NEW!
Big Pine Key, FL
2 Bedrooms | 2 Bath | Sleeps 6

The Conch-Out Cottage

$155 avg / night (excludes fees and taxes)
Key West, FL
5.0 (3)
1 Bedrooms | 2 Bath | Sleeps 5

Bay Harbor View

$272 avg / night (excludes fees and taxes)
Key West, FL
4.82 (11)
5 Bedrooms | 3 Bath | Sleeps 18

Sunset at Harbour Place

$698 avg / night (excludes fees and taxes)
Key West, FL
4.73 (59)
2 Bedrooms | 2 Bath | Sleeps 6

Louisa's Garden

$117 avg / night (excludes fees and taxes)
Key West, FL
4.67 (3)
1 Bedrooms | 1 Bath | Sleeps 2

Tarpon Watch

$214 avg / night (excludes fees and taxes)
Key West, FL
5.0 (3)
2 Bedrooms | 2 Bath | Sleeps 6

Petronia Paradise

$180 avg / night (excludes fees and taxes)
Key West, FL
4.7 (20)
2 Bedrooms | 2 Bath | Sleeps 4

Papa's Hideaway

$2,639 avg / night (excludes fees and taxes)
Key West, FL
4.95 (80)
6 Bedrooms | 6.5 Bath | Sleeps 22

Paradise Suite

$104 avg / night (excludes fees and taxes)
Key West, FL
4.5 (6)
1 Bedrooms | 1.5 Bath | Sleeps 2
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