Vacation Rentals & House Rentals in Islamorada

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53 house rentals

Key Largo Bliss: Sun, Splash, Pickleball!

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Children's pool Jacuzzi or hot tub

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Price per night from

$568

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BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$252

Paradise at Moon Bay!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$229

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$345

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$159

Tropical Island Getaway-Keys

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$338

Sunset Water Views! Moon Bay Key Largo Remodeled Condo with Boat Slip!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$315

Islamorada Waterfront Paradise | 5br | Dock | Pool

Tavernier house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 58 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$344

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$401

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$859

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,088

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$458

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$573

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$574

Paradise on the water

Key Largo house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$574

Beautifully Designed Oceanfront Condo

Tavernier apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$465

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$81

Islamorada cottage on deep water canal

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$287

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

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$984

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$390

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

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,492

Key Largo Beautiful House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$264

Coastal Key Largo Townhome with Ocean Views, Pool & Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$390

“The most relax g vacation..Awesome” We stayed at Mariners Run Key Largo.the place was beautiful,clean, state of the art appliances.there was nothing Fernanado didn't think us. my entire family raved about the rental.the pool was beautiful .we had two adjoining townhouses so it work put perfect ,more than enough room.

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$401

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

Key Largo townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$687

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$365

OCEAN VIEWS ALL ROOMS ! TOP FLOOR LARGEST CONDO

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$372

mojito breeze getaway, islamorada

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$514

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$457

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rentals in Islamorada

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