Vacation Rentals & House Rentals in Islamorada

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27 house rentals

Islamorada Waterfront Paradise Getaway!

Islamorada house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful Romantic Get-Away” We absolutely enjoyed our stay here and would recommend it to others. The owners were very friendly and pleasant, and the apartment was incredibly clean. The tiki hut over the private lagoon was amazing. We kept finding little things all over the apartment while we were there - drinks, books, games, etc. It was a totally wonderful time, and we want to go back!

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$574

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$574

Islamorada Waterfront Paradise 2

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$517

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$392

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$459

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$458

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

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Price per night from

$409

Paradise at Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$161

Majestic estate, 200' of private oceanfront beach & pool, 3,600sqft tiki

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,475

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$285

Great rentals within 20 miles that match your search

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$402

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$402

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$402

Sunrise Waterfront Home

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$488

Cozy Couple Getaway! or Great Family Home

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$144

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Matecumbe Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

“Relaxing Weekend Getaway” We love this home! It is on a private dead-end street, and everything is just perfect. Kept the boat right at the dock, fished right there at night, took some nice boat rides through the back country, and relaxed in paradise. Wifi is good and fast (I had to do some work while we were there), and we can't wait to go back.

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$173

Florida Keys Splendor at Hammer Point

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Winter Paradise!” My wife and I stayed at this great place in January 2014 and it was wonderful. It was very clean and well maintained. The canal was great to watch the fish jump and we saw Manatees almost every day. We especially liked the kayak and did a lot of site seeing from the ocean side. Migdy was great to work with and very accommodating. We would highly recommend this place to anyone.

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$158

“Beautiful property” This place is way nicer then the pictures. The property itself is breathtaking and its right on the water with a beautiful deck. I love that we had access to kayaks whenever we wanted. No one else but our party was there. The house seemed pretty clean but I wish it had a quick sweep again before we got there. The barstools had lots of dead flies. Which is weird because we didn’t have any flies around even while cooking outside. I loved that we could fish right off the deck. Just wished there was a pipe outside to wash up before going in. It’s definitely heaven, I woke up at 6 one day and enjoyed the sunrise n watching Dolfins and manitees. I would definitely stay here again.

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Price per night from

$316

Key Largo Rental Fantastic Views

Key Largo condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$402

Private Key Largo Bayside Canalfront home

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$201

Key Largo Beautiful House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$264

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$373

Luxury on the water-Clean remodeled Houseboat with great WiFi -Baycation

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$345

Oceanfront Condo w/Lake, Kayaks, Paddleboards & Bikes

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$447

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$457

Beach House 3 Bedrooms-2 Bath Key Largo

Ocean Reef house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

WAKE UP to your NATURE SPOT on the OCEAN

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 24 minutes

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Price per night from

$205

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