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Sugarloaf Key Vacation Rentals
1-24 of 120 rentals

Luxury Villa of the Setting Sun

$2,027 avg / night (excludes fees and taxes)
Near Key West , FL
4.67 (40)
4 Bedrooms | 4.5 Bath | Sleeps 8

Summerland Canal

$334 avg / night (excludes fees and taxes)
Summerland Key, FL
3.88 (8)
2 Bedrooms | 1 Bath | Sleeps 5

Endless Summerland

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

Skyway Living

$443 avg / night (excludes fees and taxes)
Summerland Key, FL
5.0 (5)
2 Bedrooms | 3.5 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 Blue Marlin

$335 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.67 (3)
2 Bedrooms | 2.5 Bath | Sleeps 6

Parrotfish Point

$335 avg / night (excludes fees and taxes)
Cudjoe Key, FL
5.0 (5)
3 Bedrooms | 3 Bath | Sleeps 6

Hawkins Lookout

$394 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.4 (5)
3 Bedrooms | 2.5 Bath | Sleeps 6

The Mermaid Manor

$606 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.0 (3)
4 Bedrooms | 4 Bath | Sleeps 10

Sunrise Suites - Cozumel Suite 112

$415 avg / night (excludes fees and taxes)
Key West, FL
4.31 (122)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Paradise Escape 407

$453 avg / night (excludes fees and taxes)
Key West, FL
4.11 (102)
2 Bedrooms | 2 Bath | Sleeps 6

Amelia House

$855 avg / night (excludes fees and taxes)
Key West, FL
4.33 (112)
3 Bedrooms | 2 Bath | Sleeps 8

Sunrise Suites - Catalina Suite 311

$358 avg / night (excludes fees and taxes)
Key West, FL
4.41 (101)
2 Bedrooms | 2 Bath | Sleeps 6

Atlantic Parrot

$660 avg / night (excludes fees and taxes)
Key West, FL
4.6 (105)
2 Bedrooms | 2 Bath | Sleeps 5

Sunrise Suites - Panama Suite 310

$413 avg / night (excludes fees and taxes)
Key West, FL
4.51 (140)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Antigua Suite 312

$436 avg / night (excludes fees and taxes)
Key West, FL
4.48 (112)
2 Bedrooms | 2 Bath | Sleeps 6

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

Sunrise Suites - Cayo Coco Suite 208

$444 avg / night (excludes fees and taxes)
Key West, FL
4.48 (135)
2 Bedrooms | 2 Bath | Sleeps 6

Old Town Garden Villas - Andros Suite

$353 avg / night (excludes fees and taxes)
Key West, FL
4.74 (136)
1 Bedrooms | 1.5 Bath | Sleeps 4

Truman Suite #3

$289 avg / night (excludes fees and taxes)
Key West, FL
4.32 (160)
0 Bedrooms | 1 Bath | Sleeps 2

Old Town Garden Villas - Abaco Suite

$514 avg / night (excludes fees and taxes)
Key West, FL
4.72 (122)
1 Bedrooms | 1.5 Bath | Sleeps 4

Sunrise Suites - Saint Croix Suite 212

$446 avg / night (excludes fees and taxes)
Key West, FL
4.12 (102)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Saint Lucia Suite 201

$427 avg / night (excludes fees and taxes)
Key West, FL
4.5 (104)
2 Bedrooms | 2 Bath | Sleeps 6

Key Lime Calypso

$902 avg / night (excludes fees and taxes)
Key West, FL
4.54 (110)
2 Bedrooms | 1 Bath | Sleeps 6
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