All Vacation Rentals

Islamorada Vacation Rentals

From oceanfront estates to bayside bungalows and everything in between, we have the perfect Islamorada vacation rental home for you. Whether youre looking for a family-friendly retreat, or a private escape for two, we have a variety of homes and condos to suit your Islamorada vacation needs.

Key Largo Vacation Rentals

With the wide selection of locally managed vacation rentals in Key Largo, we are sure we have the perfect rental for your visit.
Sort by:
Starting at (USD)

$2,500.00

Mother Ocean
Islamorada, FL
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
View Rental
Starting at (USD)

$3,000.00

Little Bay Cottage
Islamorada, FL
  • 4 Guests
  • 1 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$3,000.00

Little Bay ~ Upper
Islamorada, FL
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$3,000.00

Little Bay ~ Down
Islamorada, FL
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$3,000.00

Keys Life Cottage
Islamorada, FL
  • 5 Guests
  • 2 Bedrooms
  • 1 Bathrooms
View Rental
Starting at (USD)

$3,900.00

Cottage on Pearl
Tavernier, FL
  • 4 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$5,000.00

Keys Life Getaway
Tavernier, FL
  • 8 Guests
  • 3 Bedrooms
  • 3 Bathrooms
View Rental
Starting at (USD)

$5,000.00

Sailor's Cove
Tavernier, FL
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$5,040.00

Coral Club 204
Marathon, FL
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$5,600.00

Azalea's Cottage
Tavernier, FL
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$5,600.00

Casa Kai
Key Largo, FL
  • 10 Guests
  • 4 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$5,775.00

The Bonefish House at Tarpon Point
Islamorada, FL
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
View Rental
Starting at (USD)

$5,775.00

The Sailfish House at Tarpon Point
Islamorada, FL
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
View Rental
Starting at (USD)

$6,300.00

Executive Bay Club U2
Islamorada, FL
  • 8 Guests
  • 3 Bedrooms
  • 3 Bathrooms
View Rental
Starting at (USD)

$6,580.00

Blue Haven
Islamorada, FL
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
View Rental
Starting at (USD)

$6,750.00

Turtle Cove
Marathon, FL
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$7,000.00

The Snook House at Tarpon Point
Islamorada, FL
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
View Rental
Starting at (USD)

$7,000.00

Sunshine Villa Apartment
Tavernier, FL
  • 4 Guests
  • 1 Bedrooms
  • 1 Bathrooms
View Rental
Starting at (USD)

$8,000.00

Beach Boomer
Islamorada, FL
  • 8 Guests
  • 3 Bedrooms
  • 3 Bathrooms
View Rental
Starting at (USD)

$8,260.00

Casa Bougainvillea
Tavernier, FL
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
View Rental
Starting at (USD)

$9,000.00

Little Bay Compound
Islamorada, FL
  • 12 Guests
  • 5 Bedrooms
  • 6 Bathrooms
View Rental
Starting at (USD)

$9,000.00

Ocean Harbour, P21
Islamorada, FL
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$10,000.00

Casa Del Pirata
Islamorada, FL
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental
Starting at (USD)

$11,200.00

Casa Luca
Islamorada, FL
  • 10 Guests
  • 5 Bedrooms
  • 3 Bathrooms
View Rental
Starting at (USD)

$11,200.00

Villa Azzurra
Key Largo, FL
  • 7 Guests
  • 3 Bedrooms
  • 3 Bathrooms
View Rental