Sugarloaf Key Vacation Rentals

1-24 of 86 rentals
Luxury Villa of the Setting Sun -Near Key West Fl

Luxury Villa of the Setting Sun -Near Key West Fl

House in Sugarloaf Key, FL

Rating4.62
Persons
8Persons
Bedrooms
4Bedrooms
Bathrooms
5Bathrooms
$2,882/night
Summerland Canal

Summerland Canal

House in Summerland Key, FL

Rating3.88
Persons
5Persons
Bedrooms
2Bedrooms
Bathrooms
1Bathrooms
$235/night
Endless Summerland

Endless Summerland

House in Summerland Key, FL

Persons
6Persons
Bedrooms
3Bedrooms
Bathrooms
2Bathrooms
$423/night
Skyway Living

Skyway Living

House in Summerland Key, FL

Rating5.00
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
4Bathrooms
$288/night
Parrotfish Point

Parrotfish Point

House in Cudjoe Key, FL

Rating4.67
Persons
6Persons
Bedrooms
3Bedrooms
Bathrooms
3Bathrooms
$446/night
Hawkins Lookout

Hawkins Lookout

House in Cudjoe Key, FL

Rating4.33
Persons
6Persons
Bedrooms
3Bedrooms
Bathrooms
3Bathrooms
$274/night
The Mermaid Manor

The Mermaid Manor

House in Cudjoe Key, FL

Rating4.00
Persons
10Persons
Bedrooms
4Bedrooms
Bathrooms
4Bathrooms
$608/night
Sunrise Suites - Martinique Suite 108

Sunrise Suites - Martinique Suite 108

Condo in Key West, FL

Rating4.60
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$587/night
Leeward Isle

Leeward Isle

Cabin in Key West, FL

Rating4.45
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
1Bathrooms
$618/night
Sunrise Suites - Panama Suite 310

Sunrise Suites - Panama Suite 310

Condo in Key West, FL

Rating4.48
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$494/night
Sunrise Suites - Bonaire Suite 210

Sunrise Suites - Bonaire Suite 210

Condo in Key West, FL

Rating4.39
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$478/night
Sunrise Suites - Catalina Suite 311

Sunrise Suites - Catalina Suite 311

Condo in Key West, FL

Rating4.37
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$439/night
Three Flowers Guesthouse

Three Flowers Guesthouse

Condo in Key West, FL

Rating4.79
Persons
14Persons
Bedrooms
4Bedrooms
Bathrooms
4Bathrooms
$1,849/night
Orchid Suite

Orchid Suite

Condo in Key West, FL

Rating4.48
Persons
4Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$361/night
Tradewinds

Tradewinds

Cabin in Key West, FL

Rating4.39
Persons
12Persons
Bedrooms
4Bedrooms
Bathrooms
2Bathrooms
$1,501/night
Secret Garden

Secret Garden

Condo in Key West, FL

Rating4.59
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
1Bathrooms
$211/night
Old Town Garden Villas - Abaco Suite

Old Town Garden Villas - Abaco Suite

Condo in Key West, FL

Rating4.66
Persons
4Persons
Bedrooms
1Bedrooms
Bathrooms
2Bathrooms
$605/night
Paradise Suite

Paradise Suite

Townhouse in Key West, FL

Rating4.50
Persons
2Persons
Bedrooms
1Bedrooms
Bathrooms
2Bathrooms
$144/night
Happy Hour Haven

Happy Hour Haven

Condo in Key West, FL

Rating4.53
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$244/night
Island Retreat

Island Retreat

House in Key West, FL

Rating4.38
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
3Bathrooms
$449/night
Sunrise Suites - Cozumel Suite 112

Sunrise Suites - Cozumel Suite 112

Condo in Key West, FL

Rating4.30
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$464/night
Shipyard Perch

Shipyard Perch

Condo in Key West, FL

Rating4.81
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$157/night
Conched Out Cottage

Conched Out Cottage

House in Key West, FL

Rating5.00
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
1Bathrooms
$205/night
Seagrass Suite

Seagrass Suite

Apartment in Key West, FL

Rating4.74
Persons
2Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$433/night

© 2026 Casago LLC