Vacation Rentals & House Rentals in Islamorada

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20 house rentals

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$573

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$391

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Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Jacuzzi or hot tub, Bicycles available

1 of 2 filters match

Price per night from

$458

Islamorada Waterfront Paradise 2

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Bicycles available

1 of 2 filters match

Price per night from

$516

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!

1 of 2 match: Jacuzzi or hot tub, Bicycles available

1 of 2 filters match

Price per night from

$573

Paradise at Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Jacuzzi or hot tub, Bicycles available

1 of 2 filters match

Price per night from

$161

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Jacuzzi or hot tub, Bicycles available

1 of 2 filters match

Price per night from

$408

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Bicycles available

1 of 2 filters match

Price per night from

$457

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Bicycles available

1 of 2 filters match

Price per night from

$286

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

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Jacuzzi or hot tub, Bicycles available

1 of 2 filters match

Price per night from

$1,472

mojito breeze getaway, islamorada

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$515

Islamorada cottage on deep water canal

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$287

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$390

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 52 minutes

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$982

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

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,489

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$2,127

Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock

Islamorada villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,145

Great rentals within 20 miles that match your search

Key Largo Beautiful House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$264

Match: Bicycles available Jacuzzi or hot tub

All filters match

Price per night from

$457

WAKE UP to your NATURE SPOT on the OCEAN

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 24 minutes

Match: Bicycles available Jacuzzi or hot tub

All filters match

Price per night from

$205

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