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
$3,039/night
Endless Summerland

Endless Summerland

House in Summerland Key, FL

Persons
6Persons
Bedrooms
3Bedrooms
Bathrooms
2Bathrooms
$446/night
Skyway Living

Skyway Living

House in Summerland Key, FL

Rating5.00
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
4Bathrooms
$307/night
Summerland Canal

Summerland Canal

House in Summerland Key, FL

Rating3.88
Persons
5Persons
Bedrooms
2Bedrooms
Bathrooms
1Bathrooms
$254/night
Parrotfish Point

Parrotfish Point

House in Cudjoe Key, FL

Rating4.67
Persons
6Persons
Bedrooms
3Bedrooms
Bathrooms
3Bathrooms
$475/night
Hawkins Lookout

Hawkins Lookout

House in Cudjoe Key, FL

Rating4.33
Persons
6Persons
Bedrooms
3Bedrooms
Bathrooms
3Bathrooms
$286/night
The Mermaid Manor

The Mermaid Manor

House in Cudjoe Key, FL

Rating4.00
Persons
10Persons
Bedrooms
4Bedrooms
Bathrooms
4Bathrooms
$589/night
Sunrise Suites - Paradise Escape 407

Sunrise Suites - Paradise Escape 407

Condo in Key West, FL

Rating4.13
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$525/night
Sunrise Suites - Panama Suite 310

Sunrise Suites - Panama Suite 310

Condo in Key West, FL

Rating4.48
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$591/night
Sunrise Suites - Big Kahuna Suite 202

Sunrise Suites - Big Kahuna Suite 202

Condo in Key West, FL

Rating4.53
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$670/night
Sunrise Suites - Saint Croix Suite 212

Sunrise Suites - Saint Croix Suite 212

Condo in Key West, FL

Rating4.04
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$519/night
Oceana Suite

Oceana Suite

Condo in Key West, FL

Rating4.78
Persons
2Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$591/night
Sunrise Suites - Saint Lucia Suite 201

Sunrise Suites - Saint Lucia Suite 201

Condo in Key West, FL

Rating4.53
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$581/night
Leeward Isle

Leeward Isle

Cabin in Key West, FL

Rating4.45
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
1Bathrooms
$622/night
Sunrise Suites - Bonaire Suite 210

Sunrise Suites - Bonaire Suite 210

Condo in Key West, FL

Rating4.40
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$458/night
Sunrise Suites - Martinique Suite 108

Sunrise Suites - Martinique Suite 108

Condo in Key West, FL

Rating4.60
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$615/night
Conch Casa

Conch Casa

House in Key West, FL

Rating4.47
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
1Bathrooms
$730/night
Mermaid's Retreat

Mermaid's Retreat

Apartment in Key West, FL

Rating4.48
Persons
2Persons
Bedrooms
1Bedrooms
Bathrooms
2Bathrooms
$521/night
Paradise Suite

Paradise Suite

Townhouse in Key West, FL

Rating4.50
Persons
2Persons
Bedrooms
1Bedrooms
Bathrooms
2Bathrooms
$145/night
Sunrise Suites - Tierra Bomba Suite 403

Sunrise Suites - Tierra Bomba Suite 403

Condo in Key West, FL

Rating3.95
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$494/night
Three Flowers Guesthouse

Three Flowers Guesthouse

Condo in Key West, FL

Rating4.79
Persons
14Persons
Bedrooms
4Bedrooms
Bathrooms
4Bathrooms
$1,932/night
Gardenia Getaway

Gardenia Getaway

Condo in Key West, FL

Rating4.71
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$787/night
Sunrise Suites - Cozumel Suite 112

Sunrise Suites - Cozumel Suite 112

Condo in Key West, FL

Rating4.30
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$479/night
Sunrise Suites - Saint Barts Suite 303

Sunrise Suites - Saint Barts Suite 303

Condo in Key West, FL

Rating4.62
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$657/night

© 2026 Casago LLC