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.
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Starting at (USD)

$2,500.00

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

$3,000.00

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

$3,000.00

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

$3,000.00

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

$3,500.00

Tarpon Basin Breeze
Key Largo, FL
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
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Starting at (USD)

$3,600.00

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

$3,900.00

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

$4,500.00

Little Miss Muffet
Key Largo, FL
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
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Starting at (USD)

$4,550.00

At The Sandbar
Islamorada, FL
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
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Starting at (USD)

$4,900.00

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

$4,995.00

Peaceful Palms #15
Islamorada, FL
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
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Starting at (USD)

$5,040.00

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

$5,400.00

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

$5,500.00

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

$5,600.00

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

$5,775.00

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

$6,500.00

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

$7,000.00

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

$7,000.00

Bonito Paradise
Key Largo, FL
  • 10 Guests
  • 4 Bedrooms
  • 3 Bathrooms
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Starting at (USD)

$7,000.00

Manatee Manor
Tavernier, FL
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
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Starting at (USD)

$7,200.00

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

$7,800.00

Sand 'N Sea
Layton, FL
  • 8 Guests
  • 3 Bedrooms
  • 3 Bathrooms
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Starting at (USD)

$8,400.00

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

$9,000.00

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

$9,000.00

Ocean Harbour, P21
Islamorada, FL
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
View Rental