Vacation Rentals & House Rentals in Key Largo

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52 house rentals

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Jacuzzi or hot tub Private outdoor pool (heated)

All filters match

Price per night from

$574

Match: Jacuzzi or hot tub Private outdoor pool (heated)

All filters match

Price per night from

$2,131

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Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$201

Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Jacuzzi or hot tub, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$785

1 of 2 match: Jacuzzi or hot tub, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$912

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Jacuzzi or hot tub, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$803

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$345

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, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,474

Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool

Islamorada house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Jacuzzi or hot tub, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,148

Islamorada Ocean Views! Pool, Wi-Fi, Balcony, Gym, Covered Parking

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 44 minutes

1 of 2 match: Jacuzzi or hot tub, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$172

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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$344

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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,432

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: Private outdoor pool (heated), 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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$401

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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$573

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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,432

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: Private outdoor pool (heated), 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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

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: Private outdoor pool (heated), 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: Private outdoor pool (heated), 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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$458

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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$859

1 of 2 match: Private outdoor pool (heated), 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: Private outdoor pool (heated), 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: Private outdoor pool (heated), 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: Private outdoor pool (heated), 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: Private outdoor pool (heated), 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: Private outdoor pool (heated), 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: Private outdoor pool (heated), 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: Private outdoor pool (heated), 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: Private outdoor pool (heated), 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: Private outdoor pool (heated), 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: Private outdoor pool (heated), 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: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$687

1 of 2 match: Private outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$365

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rentals in Key Largo

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