Vacation Rentals & House Rentals in Islamorada

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30 house rentals

Bay and Beach Beauty

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 10 minutes

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Price per night from

$533

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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$345

SANCTUARY IN PARADISE

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We were tremendously blessed to have had the opportunity to share this paradise! Private, gated estate with coral wooded hammocks to stroll through, palm trees clicking in the breeze, flocks of ibis that grazed through the lush green yard that ended at the private water front. Orchids blooming in the trees welcomed us to the hammocks where we had our morning coffee to stunning colored sunrises. It had everything: super clean Keys styled house with a cute kitchen (that saved us on meal expenses), bedrooms and bathrooms that were perfect size and accommodations, and wifi. It was quiet yet welcoming to my kids. We kayaked and swam on Christmas morning! The hosts were gracious and really made us feel as we were family. It was a Christmas we will always cherish. "Give and it will be given to you. A good measure, pressed down, shaken together and running over, will be poured into your lap." Luke 6:38 Truly, after giving us the chance to come share your slice of heaven, our cup runneth over.

Responds fast! avg. 2 hours 42 minutes

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$984

Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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$447

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

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$409

Paradise at Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$161

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$1,492

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$286

Boater's Paradise

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$378

Great rentals within 20 miles that match your search

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

Beautiful Private Home with Beach Access

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Great place for a family” Wonderful place to stay! My family of 5 enjoyed the clean rooms and full kitchen. Easy access to private beach, restaurants, grocery store. Very safe neighborhood. The house was fully provided for our stay, Great access to John Pennycamp and the Everglades. We would definitely stay here again. Daniel A. was very easy to work with. We enjoyed coming home after a busy day of snorkeling to make supper and lounge on our own deck or wander down to the private beach to enjoy the evening. Having this home made our vacation very relaxing and enjoyable.

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$86

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

Private Key Largo Bayside Canalfront home

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$201

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Price per night from

$574

Key Largo Beautiful House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$264

Responds fast! avg. 3 hours 34 minutes

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$1,607

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Price per night from

$373

Island Conch Cottage

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$155

Modern house in the heart of Key Largo

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$345

Private and comfortable four bedrooms, three bath, private oasis

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$322

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

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$345

Peaceful ocean view retreat in the Florida Keys

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$259

Key Largo Bliss: Sun, Splash, Pickleball!

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$568

Cabanas Key Largo Unit 3

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 15 minutes

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Price per night from

$173

WAKE UP to your NATURE SPOT on the OCEAN

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 17 minutes

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Price per night from

$206

Key Largo Mariners Club Paradise: Largest Unit, Abundant Amenities!

Key Largo townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$689

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

$345

OCEAN VIEWS ALL ROOMS ! TOP FLOOR LARGEST CONDO

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$373

LICENSED MGR. - LUXURIOUS OCEANFRONT CONDO! - W/STUNNING OCEAN/ISLAND VIEWS!

Key Largo hotel apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$402

Bayside home with dock!

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Peaceful stay in Key Largo” I stayed at the Bayside home from 12/31/14-1/6/15 and it was wonderful. Joy and Doug were very accommodating and available for any and all questions. The place was perfect to sit and enjoy the beautiful sunsets or greet the fellow boaters passing through the canal. It was a perfect midpoint between Key West and Miami. Thanks, Joy and Doug for a wonderful stay!

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Price per night from

$276

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