Islamorada Vacation Rentals

From oceanfront estates to bayside bungalows and everything in between, we have the perfect Islamorada vacation rental home for you. Whether you're 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.

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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)

$3,000.00

Keys Life Cottage
Islamorada, FL
  • 5 Guests
  • 2 Bedrooms
  • 1 Bathrooms
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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)

$6,300.00

Executive Bay Club U2
Islamorada, FL
  • 8 Guests
  • 3 Bedrooms
  • 3 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)

$8,000.00

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

$9,000.00

Ocean Harbour, P21
Islamorada, FL
  • 8 Guests
  • 3 Bedrooms
  • 2 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)

$10,000.00

Casa Del Pirata
Islamorada, FL
  • 6 Guests
  • 3 Bedrooms
  • 2 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)

$13,200.00

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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Starting at (USD)

$17,500.00

Manatee Harbor
Tavernier, FL
  • 12 Guests
  • 4 Bedrooms
  • 5 Bathrooms
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