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)

$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)

$3,900.00

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

$4,500.00

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

$5,000.00

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

$5,000.00

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

$5,600.00

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

$5,800.00

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

$5,900.00

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

$6,000.00

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

$6,000.00

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

$6,020.00

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

$6,300.00

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

$7,000.00

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

$7,500.00

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

$7,700.00

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

$7,700.00

Beach Boomer
Islamorada, FL
  • 8 Guests
  • 3 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)

$11,200.00

Villa Azzurra
Key Largo, FL
  • 7 Guests
  • 3 Bedrooms
  • 3 Bathrooms
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Starting at (USD)

$11,200.00

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

$12,500.00

Caribee Beach House
Islamorada, FL
  • 14 Guests
  • 6 Bedrooms
  • 5 Bathrooms
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Starting at (USD)

$14,000.00

Harbor Hideaway
Islamorada, FL
  • 11 Guests
  • 4 Bedrooms
  • 3 Bathrooms
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Starting at (USD)

$16,100.00

Bayview Paradise
Islamorada, FL
  • 9 Guests
  • 3 Bedrooms
  • 3 Bathrooms
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