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Sugarloaf Key Vacation Rentals
1-24 of 120 rentals

Luxury Villa of the Setting Sun

$2,019 avg / night (excludes fees and taxes)
Near Key West , FL
4.67 (40)
4 Bedrooms | 4.5 Bath | Sleeps 8

Summerland Canal

$332 avg / night (excludes fees and taxes)
Summerland Key, FL
3.88 (8)
2 Bedrooms | 1 Bath | Sleeps 5

Endless Summerland

$326 avg / night (excludes fees and taxes)
NEW!
Summerland Key, FL
3 Bedrooms | 2 Bath | Sleeps 6

Skyway Living

$438 avg / night (excludes fees and taxes)
Summerland Key, FL
5.0 (5)
2 Bedrooms | 3.5 Bath | Sleeps 6

Dock Holiday

$265 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.48 (25)
2 Bedrooms | 2 Bath | Sleeps 4

The Blue Marlin

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

Parrotfish Point

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

Hawkins Lookout

$392 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.4 (5)
3 Bedrooms | 2.5 Bath | Sleeps 6

The Mermaid Manor

$600 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.0 (3)
4 Bedrooms | 4 Bath | Sleeps 10

Amelia House

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

Sunrise Suites - Tierra Bomba Suite 403

$429 avg / night (excludes fees and taxes)
Key West, FL
3.96 (90)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Cozumel Suite 112

$413 avg / night (excludes fees and taxes)
Key West, FL
4.31 (122)
2 Bedrooms | 2 Bath | Sleeps 6

Truman Suite #3

$285 avg / night (excludes fees and taxes)
Key West, FL
4.32 (160)
0 Bedrooms | 1 Bath | Sleeps 2

Sunrise Suites - Saint Croix Suite 212

$445 avg / night (excludes fees and taxes)
Key West, FL
4.12 (102)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Paradise Escape 407

$452 avg / night (excludes fees and taxes)
Key West, FL
4.11 (102)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Panama Suite 310

$407 avg / night (excludes fees and taxes)
Key West, FL
4.51 (140)
2 Bedrooms | 2 Bath | Sleeps 6

Hemingway's View

$1,014 avg / night (excludes fees and taxes)
Key West, FL
4.41 (131)
3 Bedrooms | 2 Bath | Sleeps 7

Old Town Garden Villas - Abaco Suite

$509 avg / night (excludes fees and taxes)
Key West, FL
4.72 (122)
1 Bedrooms | 1.5 Bath | Sleeps 4

Sunrise Suites - Cayo Coco Suite 208

$442 avg / night (excludes fees and taxes)
Key West, FL
4.48 (135)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Antigua Suite 312

$431 avg / night (excludes fees and taxes)
Key West, FL
4.48 (112)
2 Bedrooms | 2 Bath | Sleeps 6

Atlantic Parrot

$652 avg / night (excludes fees and taxes)
Key West, FL
4.6 (104)
2 Bedrooms | 2 Bath | Sleeps 5

Old Town Garden Villas - Andros Suite

$351 avg / night (excludes fees and taxes)
Key West, FL
4.75 (135)
1 Bedrooms | 1.5 Bath | Sleeps 4

Sunrise Suites - Barbados Suite 204

$472 avg / night (excludes fees and taxes)
Key West, FL
4.17 (137)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Bonaire Suite 210

$407 avg / night (excludes fees and taxes)
Key West, FL
4.45 (109)
2 Bedrooms | 2 Bath | Sleeps 6
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