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Summerland Key Vacation Rentals
1-24 of 116 rentals

Summerland Canal

$344 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

$449 avg / night (excludes fees and taxes)
Summerland Key, FL
5.0 (5)
2 Bedrooms | 3.5 Bath | Sleeps 6

Dock Holiday

$268 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

$344 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.67 (3)
2 Bedrooms | 2.5 Bath | Sleeps 6

The Mermaid Manor

$643 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.0 (3)
4 Bedrooms | 4 Bath | Sleeps 10

Hawkins Lookout

$399 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.4 (5)
3 Bedrooms | 2.5 Bath | Sleeps 6

Luxury Villa of the Setting Sun -Near Key West Fl

$2,038 avg / night (excludes fees and taxes)
Near Key West , FL
4.68 (41)
4 Bedrooms | 4.5 Bath | Sleeps 8

Salty Air Retreat

$311 avg / night (excludes fees and taxes)
NEW!
Little Torch Key, FL
3 Bedrooms | 2 Bath | Sleeps 8

Torchbearer - Lower

$201 avg / night (excludes fees and taxes)
NEW!
Little Torch Key, FL
2 Bedrooms | 1 Bath | Sleeps 6

Cayo Loco

$313 avg / night (excludes fees and taxes)
Little Torch Key, FL
4.5 (2)
3 Bedrooms | 2 Bath | Sleeps 6

Sunset Villa

$273 avg / night (excludes fees and taxes)
Big Pine Key, FL
4.0 (3)
3 Bedrooms | 2 Bath | Sleeps 6

Big Pine Bungalow

$322 avg / night (excludes fees and taxes)
NEW!
Big Pine Key, FL
3 Bedrooms | 2 Bath | Sleeps 7

Big Pine Key Dreams

$284 avg / night (excludes fees and taxes)
Big Pine Key, FL
4.83 (6)
2 Bedrooms | 2 Bath | Sleeps 6

The Nautical Nimbus

$352 avg / night (excludes fees and taxes)
Big Pine Key, FL
4.67 (3)
3 Bedrooms | 2 Bath | Sleeps 6

Tradewinds Treat

$270 avg / night (excludes fees and taxes)
NEW!
Big Pine Key, FL
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Panama Suite 310

$429 avg / night (excludes fees and taxes)
Key West, FL
4.51 (140)
2 Bedrooms | 2 Bath | Sleeps 6

Old Town Garden Villas - Andros Suite

$371 avg / night (excludes fees and taxes)
Key West, FL
4.75 (138)
1 Bedrooms | 1.5 Bath | Sleeps 4

Sunrise Suites - Dominican Suite 110

$453 avg / night (excludes fees and taxes)
Key West, FL
4.41 (108)
2 Bedrooms | 2 Bath | Sleeps 6

Old Town Garden Villas - Abaco Suite

$527 avg / night (excludes fees and taxes)
Key West, FL
4.72 (122)
1 Bedrooms | 1.5 Bath | Sleeps 4

Key Lime Calypso

$920 avg / night (excludes fees and taxes)
Key West, FL
4.54 (110)
2 Bedrooms | 1 Bath | Sleeps 6

Sunrise Suites - Paradise Escape 407

$465 avg / night (excludes fees and taxes)
Key West, FL
4.1 (103)
2 Bedrooms | 2 Bath | Sleeps 6

Sunrise Suites - Catalina Suite 311

$363 avg / night (excludes fees and taxes)
Key West, FL
4.37 (104)
2 Bedrooms | 2 Bath | Sleeps 6
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