All Vacation Rentals

Sort by:
Starting at (USD)

$450.00

Villa Ambriana: Sunset Key Residence
Key West, FL
  • 8 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
View Rental
Starting at (USD)

$4,500.00

Sugarloaf Serenity
Summerland Key, FL
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$4,000.00

Sunshine 23
Summerland Key, FL
  • 5 Guests
  • 2 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$3,750.00

Cayman Cottage
Ramrod Key, FL
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$5,500.00

Foster's Folly
Summerland Key, FL
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental
Key West, FL
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Pets Allowed
View Rental
Starting at (USD)

$3,500.00

Calico Jack Hideaway
Cudjoe Key, FL
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental
Key West, FL
  • 8 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
View Rental
Starting at (USD)

$3,500.00

Key Deer Hideaway
Big Pine Key, FL
  • 7 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$3,750.00

Blackbeard's Hideaway
Summerland Key, FL
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$3,500.00

Cedar Cottage
Big Pine Key, FL
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$6,500.00

Caribbean Retreat
Summerland Key, FL
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
View Rental
Starting at (USD)

$4,500.00

Latitude Adjustment
Summerland Key, FL
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$5,500.00

Ocean Blue
Summerland Key, FL
  • 8 Guests
  • 3 Bedrooms
  • 3 Bathrooms
View Rental
Starting at (USD)

$3,250.00

Bogie Cottage
Big Pine Key, FL
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$3,750.00

Paradise Found
Cudjoe Key, FL
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$3,500.00

El Paraiso
Cudjoe Key, FL
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$228.00

Portside Villa
Key West, FL
  • 8 Guests
  • 3 Bedrooms
  • 3.5 Bathrooms
View Rental
Starting at (USD)

$116.00

Egret House at the Key West Golf Club
Key West, FL
  • 6 Guests
  • 2 Bedrooms
  • 1 Bathrooms
View Rental