Vacation Rentals & House Rentals in Islamorada

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50 house rentals

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

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Price per night from

$248

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ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$776

FALL IN LOVE with your home away from home!

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$207

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

1 of 2 filters match

Price per night from

$914

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 20 minutes

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

1 of 2 filters match

Price per night from

$403

Key Largo Ocean Front Villa with Dock and Incredible views

Key Largo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 20 minutes

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

1 of 2 filters match

Price per night from

$460

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$487

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$1,145

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$1,775

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$916

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$687

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

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

1 of 2 filters match

Price per night from

$1,775

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 (unheated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$345

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

1 of 2 filters match

Price per night from

$575

Paradise on the water

Key Largo house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$575

Beautifully Designed Oceanfront Condo

Tavernier apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$466

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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

1 of 2 filters match

Price per night from

$288

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$391

2 BEDROOM 2 1/2 BATH VILLA WITH PRIVATE PATIO AND PLUNGE POOL

Duck Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 13 minutes

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

1 of 2 filters match

Price per night from

$340

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 (unheated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$690

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 33 minutes

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

1 of 2 filters match

Price per night from

$986

Key Largo Beautiful House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$265

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 (unheated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,495

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 (unheated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$391

OCEAN VIEWS ALL ROOMS ! TOP FLOOR LARGEST CONDO

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$374

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

Key Largo hotel apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$403

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

1 of 2 filters match

Price per night from

$459

“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 (unheated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$403

“Wonderful family vacation!” We had a wonderful time in Key Largo staying in this beautiful townhouse. The house was very clean and looked exactly like it was advertised. We have two children ages 16 and 12, and it was very enjoyable with each of them being able to have their own bedroom and bathroom. The pools and hot tubs at this resort are absolutely beautiful. Also, there is a restaurant right next to the resort that has wonderful food and music. We would definitely stay here again and highly recommend it to others.

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

1 of 2 filters match

Price per night from

$374

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

1 of 2 filters match

Price per night from

$367

mojito breeze getaway, islamorada

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

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

1 of 2 filters match

Price per night from

$517

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