Summerland Key Vacation Rentals
1-24 of 91 rentals
Endless Summerland
House in Summerland Key, FL
6Persons
3Bedrooms
2Bathrooms
$392/night
Summerland Canal
House in Summerland Key, FL
5Persons
2Bedrooms
1Bathrooms
$363/night
Skyway Living
House in Summerland Key, FL
6Persons
2Bedrooms
4Bathrooms
$321/night
The Mermaid Manor
House in Cudjoe Key, FL
10Persons
4Bedrooms
4Bathrooms
$591/night
Parrotfish Point
House in Cudjoe Key, FL
6Persons
3Bedrooms
3Bathrooms
$448/night
Hawkins Lookout
House in Cudjoe Key, FL
6Persons
3Bedrooms
3Bathrooms
$298/night
Luxury Villa of the Setting Sun -Near Key West Fl
House in Sugarloaf Key, FL
8Persons
4Bedrooms
5Bathrooms
$2,707/night
Tobago Stars
House in Ramrod Key, FL
5Persons
3Bedrooms
2Bathrooms
$303/night
Torchbearer - Lower
House in Little Torch Key, FL
6Persons
2Bedrooms
1Bathrooms
$319/night
Salty Air Retreat
House in Little Torch Key, FL
8Persons
3Bedrooms
2Bathrooms
$420/night
Big Pine Bungalow
House in Big Pine Key, FL
7Persons
3Bedrooms
2Bathrooms
$245/night
Big Pine Key Dreams
House in Big Pine Key, FL
6Persons
2Bedrooms
2Bathrooms
$241/night
Tradewinds Treat
House in Big Pine Key, FL
6Persons
2Bedrooms
2Bathrooms
$332/night
Big Pine Escape
House in Big Pine Key, FL
6Persons
3Bedrooms
2Bathrooms
$351/night
Octopus Palms
House in Big Pine Key, FL
6Persons
3Bedrooms
1Bathrooms
$255/night
Sunset Villa
House in Big Pine Key, FL
6Persons
3Bedrooms
2Bathrooms
$260/night
Tropical Valhalla
House in Big Pine Key, FL
8Persons
3Bedrooms
2Bathrooms
$377/night
Leeward Isle
Cabin in Key West, FL
6Persons
2Bedrooms
1Bathrooms
$580/night
Sunrise Suites - Panama Suite 310
Condo in Key West, FL
4Persons
2Bedrooms
2Bathrooms
$470/night
Oceana Suite
Condo in Key West, FL
2Persons
1Bedrooms
1Bathrooms
$500/night
Conch Casa
House in Key West, FL
4Persons
2Bedrooms
1Bathrooms
$673/night
Seagrass Suite
Apartment in Key West, FL
2Persons
1Bedrooms
1Bathrooms
$420/night
Tradewinds at Smathers Beach
Condo in Key West, FL
8Persons
3Bedrooms
2Bathrooms
$301/night
Conch Island
Townhouse in Key West, FL
4Persons
2Bedrooms
1Bathrooms
$384/night