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Summerland Key Vacation Rentals
1-24 of 128 rentals

Endless Summerland

$482 avg / night (excludes fees and taxes)
NEW!
Summerland Key, FL
3 Bedrooms | 2 Bath | Sleeps 6

Summerland Canal

$463 avg / night (excludes fees and taxes)
Summerland Key, FL
3.88 (8)
2 Bedrooms | 1 Bath | Sleeps 5

Skyway Living

$633 avg / night (excludes fees and taxes)
Summerland Key, FL
5.0 (5)
2 Bedrooms | 3.5 Bath | Sleeps 6

Dock Holiday

$388 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.46 (24)
2 Bedrooms | 2 Bath | Sleeps 4

Hawkins Lookout

$574 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.4 (5)
3 Bedrooms | 2.5 Bath | Sleeps 6

The Mermaid Manor

$860 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.0 (3)
4 Bedrooms | 4 Bath | Sleeps 10

Parrotfish Point

$607 avg / night (excludes fees and taxes)
Cudjoe Key, FL
5.0 (4)
3 Bedrooms | 3 Bath | Sleeps 6

The Blue Marlin

$538 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.5 (2)
2 Bedrooms | 2.5 Bath | Sleeps 6

Luxury Villa of the Setting Sun

$2,831 avg / night (excludes fees and taxes)
Near Key West , FL
4.67 (39)
4 Bedrooms | 4.5 Bath | Sleeps 8

Salty Air Retreat

$450 avg / night (excludes fees and taxes)
NEW!
Little Torch Key, FL
3 Bedrooms | 2 Bath | Sleeps 8

Torchbearer - Lower

$295 avg / night (excludes fees and taxes)
NEW!
Little Torch Key, FL
2 Bedrooms | 1 Bath | Sleeps 6

Cayo Loco

$447 avg / night (excludes fees and taxes)
Little Torch Key, FL
4.5 (2)
3 Bedrooms | 2 Bath | Sleeps 6

Big Pine Key Dreams

$443 avg / night (excludes fees and taxes)
Big Pine Key, FL
4.8 (5)
2 Bedrooms | 2 Bath | Sleeps 6

Big Pine Bungalow

$645 avg / night (excludes fees and taxes)
NEW!
Big Pine Key, FL
3 Bedrooms | 2 Bath | Sleeps 7

The Nautical Nimbus

$492 avg / night (excludes fees and taxes)
Big Pine Key, FL
4.67 (3)
3 Bedrooms | 2 Bath | Sleeps 6

Sunset Villa

$422 avg / night (excludes fees and taxes)
Big Pine Key, FL
4.0 (3)
3 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Cozumel Suite 112

$498 avg / night (excludes fees and taxes)
Key West, FL
4.35 (117)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Paradise Escape 407

$564 avg / night (excludes fees and taxes)
Key West, FL
4.12 (99)
2 Bedrooms | 2 Bath | Sleeps 6

Truman Suite #3

$354 avg / night (excludes fees and taxes)
Key West, FL
4.32 (156)
0 Bedrooms | 1 Bath | Sleeps 2

Sunrise Suites - Tahiti Suite 104

$629 avg / night (excludes fees and taxes)
Key West, FL
4.72 (136)
2 Bedrooms | 2 Bath | Sleeps 6

Old Town Garden Villas - Andros Suite

$528 avg / night (excludes fees and taxes)
Key West, FL
4.74 (132)
1 Bedrooms | 1.5 Bath | Sleeps 4

Sunrise Suites - Dominican Suite 110

$557 avg / night (excludes fees and taxes)
Key West, FL
4.46 (102)
2 Bedrooms | 2 Bath | Sleeps 6

Leeward Isle

$662 avg / night (excludes fees and taxes)
Key West, FL
4.52 (67)
2 Bedrooms | 1 Bath | Sleeps 6

Sunrise Suites - Saint Croix Suite 212

$581 avg / night (excludes fees and taxes)
Key West, FL
4.12 (100)
2 Bedrooms | 2 Bath | Sleeps 6
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