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Summerland Key Vacation Rentals
1-18 of 18 rentals

Skyway Living

$262 avg / night (excludes fees and taxes)
Summerland Key, FL
5.0 (5)
2 Bedrooms | 3.5 Bath | Sleeps 6

Dock Holiday

$244 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.48 (25)
2 Bedrooms | 2 Bath | Sleeps 4

Hawkins Lookout

$232 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.4 (5)
3 Bedrooms | 2.5 Bath | Sleeps 6

Parrotfish Point

$305 avg / night (excludes fees and taxes)
Cudjoe Key, FL
5.0 (5)
3 Bedrooms | 3 Bath | Sleeps 6

The Mermaid Manor

$390 avg / night (excludes fees and taxes)
Cudjoe Key, FL
4.0 (3)
4 Bedrooms | 4 Bath | Sleeps 10

Luxury Villa of the Setting Sun -Near Key West Fl

$2,028 avg / night (excludes fees and taxes)
Near Key West , FL
4.68 (41)
4 Bedrooms | 4.5 Bath | Sleeps 8

Salty Air Retreat

$225 avg / night (excludes fees and taxes)
NEW!
Little Torch Key, FL
3 Bedrooms | 2 Bath | Sleeps 8

Torchbearer - Lower

$173 avg / night (excludes fees and taxes)
NEW!
Little Torch Key, FL
2 Bedrooms | 1 Bath | Sleeps 6

Cayo Loco

$228 avg / night (excludes fees and taxes)
Little Torch Key, FL
4.5 (2)
3 Bedrooms | 2 Bath | Sleeps 6

Big Pine Key Dreams

$165 avg / night (excludes fees and taxes)
Big Pine Key, FL
4.83 (6)
2 Bedrooms | 2 Bath | Sleeps 6

Sunset Villa

$199 avg / night (excludes fees and taxes)
Big Pine Key, FL
4.0 (3)
3 Bedrooms | 2 Bath | Sleeps 6

Tradewinds Treat

$234 avg / night (excludes fees and taxes)
NEW!
Big Pine Key, FL
2 Bedrooms | 2 Bath | Sleeps 6

Sapphire Sabbatical

$166 avg / night (excludes fees and taxes)
Key West, FL
5.0 (5)
3 Bedrooms | 2 Bath | Sleeps 6

Jewel on Jade

$184 avg / night (excludes fees and taxes)
NEW!
Key West, FL
2 Bedrooms | 2 Bath | Sleeps 6

The North Star

$172 avg / night (excludes fees and taxes)
NEW!
Key West, FL
2 Bedrooms | 2 Bath | Sleeps 4

Sunset Bay

$355 avg / night (excludes fees and taxes)
Key West, FL
5.0 (26)
4 Bedrooms | 3 Bath | Sleeps 11

Coral Queen Palm

$274 avg / night (excludes fees and taxes)
NEW!
Key West, FL
3 Bedrooms | 2 Bath | Sleeps 6

Bay Harbor View

$211 avg / night (excludes fees and taxes)
Key West, FL
4.82 (11)
5 Bedrooms | 3 Bath | Sleeps 18
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