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Sugarloaf Key Vacation Rentals
1-24 of 128 rentals

Luxury Villa of the Setting Sun

$2,832 avg / night (excludes fees and taxes)
Near Key West , FL
4.67 (39)
4 Bedrooms | 4.5 Bath | Sleeps 8

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

$634 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

$862 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.0 (3)
4 Bedrooms | 4 Bath | Sleeps 10

The Blue Marlin

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

Parrotfish Point

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

$565 avg / night (excludes fees and taxes)
Key West, FL
4.13 (100)
2 Bedrooms | 2 Bath | Sleeps 6

Truman Suite #3

$351 avg / night (excludes fees and taxes)
Key West, FL
4.32 (156)
0 Bedrooms | 1 Bath | Sleeps 2

Sunrise Suites - Tahiti Suite 104

$631 avg / night (excludes fees and taxes)
Key West, FL
4.72 (136)
2 Bedrooms | 2 Bath | Sleeps 6

Old Town Garden Villas - Andros Suite

$529 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

$680 avg / night (excludes fees and taxes)
Key West, FL
4.52 (67)
2 Bedrooms | 1 Bath | Sleeps 6

Sunrise Suites - Saint Croix Suite 212

$583 avg / night (excludes fees and taxes)
Key West, FL
4.12 (100)
2 Bedrooms | 2 Bath | Sleeps 6

Orchid Suite

$388 avg / night (excludes fees and taxes)
Key West, FL
4.51 (80)
1 Bedrooms | 1 Bath | Sleeps 4

Old Town Garden Villas - Abaco Suite

$794 avg / night (excludes fees and taxes)
Key West, FL
4.71 (117)
1 Bedrooms | 1.5 Bath | Sleeps 4

Sunrise Suites - Cayo Coco Suite 208

$544 avg / night (excludes fees and taxes)
Key West, FL
4.5 (129)
2 Bedrooms | 2 Bath | Sleeps 6

Passover Cottage

$758 avg / night (excludes fees and taxes)
Key West, FL
4.85 (165)
2 Bedrooms | 2 Bath | Sleeps 4

Audubon House #6

$548 avg / night (excludes fees and taxes)
Key West, FL
4.69 (139)
1 Bedrooms | 2 Bath | Sleeps 2

Sunrise Suites - Saint Kitts 412

$570 avg / night (excludes fees and taxes)
Key West, FL
4.41 (75)
2 Bedrooms | 2 Bath | Sleeps 4

Tradewinds

$1,758 avg / night (excludes fees and taxes)
Key West, FL
4.42 (57)
4 Bedrooms | 2 Bath | Sleeps 12
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