Vacation Rentals & House Rentals in Islamorada

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13 house rentals

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Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$229

Bayside Condo, marina, pool and beach

Islamorada condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Phenomenal keys experience!” This bay front condo is the perfect destination for the entire family! The fishing ranks up with the best in the world, there are plenty of other activities, and Key West is just a short trip down the beautiful HWY 1. I've had the pleasure of staying at this condo several times and have honestly never had a bad time (even during a cat 5 Trop Storm). There is too much to do, the condo is comfy, and the weather is always beautiful. Definitely recommend this condo!

Match: Wheelchair accessible

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Price per night from

$253

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Wheelchair accessible

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Price per night from

$799

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$388

Keys Kottage

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$314

Boater's Paradise

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Wheelchair accessible

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Price per night from

$376

Great rentals within 20 miles that match your search

Cozy Couple Getaway! or Great Family Home

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$143

Match: Wheelchair accessible

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Price per night from

$371

Ocean view condo with balcony

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$314

Cabanas Key Largo Unit 3

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 15 minutes

Match: Wheelchair accessible

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Price per night from

$172

Paradise at Moon Bay!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Wheelchair accessible

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Price per night from

$229

WAKE UP to your NATURE SPOT on the OCEAN

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 17 minutes

Match: Wheelchair accessible

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Price per night from

$205

Penthouse Sunsets and Tropical Breeze in Key Largo

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place for a family of 5” Loved the condo, it was family friendly and very spacious. We had a great view from our deck. The owner was very friendly and very helpful. The facility had a great tennis court and we loved the lagoon. This unit was a great value and the owner makes it affordable for the average family to be able to spend time there.

Match: Wheelchair accessible

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Price per night from

$314

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