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Sugarloaf Key Vacation Rentals
1-24 of 120 rentals

Luxury Villa of the Setting Sun

$2,022 avg / night (excludes fees and taxes)
Near Key West , FL
4.67 (40)
4 Bedrooms | 4.5 Bath | Sleeps 8

Endless Summerland

$328 avg / night (excludes fees and taxes)
NEW!
Summerland Key, FL
3 Bedrooms | 2 Bath | Sleeps 6

Skyway Living

$441 avg / night (excludes fees and taxes)
Summerland Key, FL
5.0 (5)
2 Bedrooms | 3.5 Bath | Sleeps 6

Summerland Canal

$333 avg / night (excludes fees and taxes)
Summerland Key, FL
3.88 (8)
2 Bedrooms | 1 Bath | Sleeps 5

Parrotfish Point

$334 avg / night (excludes fees and taxes)
Cudjoe Key, FL
5.0 (5)
3 Bedrooms | 3 Bath | Sleeps 6

Hawkins Lookout

$393 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.4 (5)
3 Bedrooms | 2.5 Bath | Sleeps 6

The Blue Marlin

$330 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.67 (3)
2 Bedrooms | 2.5 Bath | Sleeps 6

Dock Holiday

$266 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.48 (25)
2 Bedrooms | 2 Bath | Sleeps 4

The Mermaid Manor

$603 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.0 (3)
4 Bedrooms | 4 Bath | Sleeps 10

The Conch-Out Cottage

$163 avg / night (excludes fees and taxes)
Key West, FL
5.0 (3)
1 Bedrooms | 2 Bath | Sleeps 5

Sunset at Harbour Place

$748 avg / night (excludes fees and taxes)
Key West, FL
4.73 (59)
2 Bedrooms | 2 Bath | Sleeps 6

Bay Harbor View

$480 avg / night (excludes fees and taxes)
Key West, FL
4.8 (10)
5 Bedrooms | 3 Bath | Sleeps 18

Louisa's Garden

$161 avg / night (excludes fees and taxes)
Key West, FL
4.67 (3)
1 Bedrooms | 1 Bath | Sleeps 2

Papa's Hideaway

$2,654 avg / night (excludes fees and taxes)
Key West, FL
4.95 (79)
6 Bedrooms | 6.5 Bath | Sleeps 22

Tarpon Watch

$288 avg / night (excludes fees and taxes)
Key West, FL
5.0 (2)
2 Bedrooms | 2 Bath | Sleeps 6

Orchid Suite

$195 avg / night (excludes fees and taxes)
Key West, FL
4.52 (83)
1 Bedrooms | 1 Bath | Sleeps 4

Petronia Paradise

$198 avg / night (excludes fees and taxes)
Key West, FL
4.68 (19)
2 Bedrooms | 2 Bath | Sleeps 4

Atlantic Ocean View

$702 avg / night (excludes fees and taxes)
Key West, FL
4.18 (92)
2 Bedrooms | 2 Bath | Sleeps 6

The Orchid House

$472 avg / night (excludes fees and taxes)
NEW!
Key West, FL
3 Bedrooms | 3 Bath | Sleeps 8

Audubon House #6

$437 avg / night (excludes fees and taxes)
Key West, FL
4.69 (139)
1 Bedrooms | 2 Bath | Sleeps 2

Sunset Bay

$490 avg / night (excludes fees and taxes)
Key West, FL
5.0 (25)
4 Bedrooms | 3 Bath | Sleeps 11

Paradise Suite

$114 avg / night (excludes fees and taxes)
Key West, FL
4.4 (5)
1 Bedrooms | 1.5 Bath | Sleeps 2

Sunrise Suites - Tierra Bomba Suite 403

$431 avg / night (excludes fees and taxes)
Key West, FL
3.96 (90)
2 Bedrooms | 2 Bath | Sleeps 6

Papa's Hideaway #1 - Torrents of Spring

$283 avg / night (excludes fees and taxes)
Key West, FL
4.76 (75)
0 Bedrooms | 1 Bath | Sleeps 4
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