Check in
Check out
1 guest
Filters
Map
Sugarloaf Key Vacation Rentals
1-24 of 119 rentals

Luxury Villa of the Setting Sun -Near Key West Fl

$2,036 avg / night (excludes fees and taxes)
Near Key West , FL
4.68 (41)
4 Bedrooms | 4.5 Bath | Sleeps 8

Summerland Canal

$343 avg / night (excludes fees and taxes)
Summerland Key, FL
3.88 (8)
2 Bedrooms | 1 Bath | Sleeps 5

Endless Summerland

$332 avg / night (excludes fees and taxes)
NEW!
Summerland Key, FL
3 Bedrooms | 2 Bath | Sleeps 6

Skyway Living

$448 avg / night (excludes fees and taxes)
Summerland Key, FL
5.0 (5)
2 Bedrooms | 3.5 Bath | Sleeps 6

Dock Holiday

$267 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.48 (25)
2 Bedrooms | 2 Bath | Sleeps 4

Parrotfish Point

$342 avg / night (excludes fees and taxes)
Cudjoe Key, FL
5.0 (5)
3 Bedrooms | 3 Bath | Sleeps 6

The Blue Marlin

$343 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.67 (3)
2 Bedrooms | 2.5 Bath | Sleeps 6

Hawkins Lookout

$398 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.4 (5)
3 Bedrooms | 2.5 Bath | Sleeps 6

The Mermaid Manor

$642 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.0 (3)
4 Bedrooms | 4 Bath | Sleeps 10

Sunrise Suites - Panama Suite 310

$428 avg / night (excludes fees and taxes)
Key West, FL
4.51 (140)
2 Bedrooms | 2 Bath | Sleeps 6

Old Town Garden Villas - Andros Suite

$370 avg / night (excludes fees and taxes)
Key West, FL
4.75 (138)
1 Bedrooms | 1.5 Bath | Sleeps 4

Sunrise Suites - Dominican Suite 110

$452 avg / night (excludes fees and taxes)
Key West, FL
4.41 (108)
2 Bedrooms | 2 Bath | Sleeps 6

Old Town Garden Villas - Abaco Suite

$528 avg / night (excludes fees and taxes)
Key West, FL
4.72 (122)
1 Bedrooms | 1.5 Bath | Sleeps 4

Key Lime Calypso

$919 avg / night (excludes fees and taxes)
Key West, FL
4.54 (110)
2 Bedrooms | 1 Bath | Sleeps 6

Sunrise Suites - Paradise Escape 407

$464 avg / night (excludes fees and taxes)
Key West, FL
4.1 (103)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Catalina Suite 311

$361 avg / night (excludes fees and taxes)
Key West, FL
4.37 (103)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Saint Croix Suite 212

$454 avg / night (excludes fees and taxes)
Key West, FL
4.12 (102)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Tierra Bomba Suite 403

$440 avg / night (excludes fees and taxes)
Key West, FL
3.96 (90)
2 Bedrooms | 2 Bath | Sleeps 6

Tradewinds

$1,128 avg / night (excludes fees and taxes)
Key West, FL
4.44 (59)
4 Bedrooms | 2 Bath | Sleeps 12

Leeward Isle

$228 avg / night (excludes fees and taxes)
Key West, FL
4.5 (72)
2 Bedrooms | 1 Bath | Sleeps 6

Papa's Hideaway

$2,635 avg / night (excludes fees and taxes)
Key West, FL
4.95 (79)
6 Bedrooms | 6.5 Bath | Sleeps 22

Hemingway Hideaway

$578 avg / night (excludes fees and taxes)
Key West, FL
4.34 (111)
3 Bedrooms | 3 Bath | Sleeps 6

Hemingway's View

$1,027 avg / night (excludes fees and taxes)
Key West, FL
4.41 (131)
3 Bedrooms | 2 Bath | Sleeps 7

Mermaid's Retreat

$379 avg / night (excludes fees and taxes)
Key West, FL
4.57 (21)
1 Bedrooms | 1.5 Bath | Sleeps 2
Page 1 of 5
Su
Mo
Tu
We
Th
Fr
Sa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
Su
Mo
Tu
We
Th
Fr
Sa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5