Vacation Rentals & House Rentals in Islamorada

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41 house rentals

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Responds fast! avg. 1 hour 0 minutes

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Price per night from

$670

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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Price per night from

$982

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$802

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Price per night from

$2,131

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

Islamorada house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$1,148

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

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Price per night from

$409

Keys Kottage

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$315

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

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,475

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1 of 2 match: Balcony or terrace, Pets allowed

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Price per night from

$912

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

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Balcony or terrace, Pets allowed

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Price per night from

$785

Boater's Paradise

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Balcony or terrace, Pets allowed

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Price per night from

$377

Manatee Bay

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$261

Beachfront Islamorada Villa with Dockage and Bay Views

Lower Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$349

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$458

Bayside Condo, marina, pool and beach

Islamorada condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Phenomenal keys experience!” This bay front condo is the perfect destination for the entire family! The fishing ranks up with the best in the world, there are plenty of other activities, and Key West is just a short trip down the beautiful HWY 1. I've had the pleasure of staying at this condo several times and have honestly never had a bad time (even during a cat 5 Trop Storm). There is too much to do, the condo is comfy, and the weather is always beautiful. Definitely recommend this condo!

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$253

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

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$1,492

Paradise at Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$161

mojito breeze getaway, islamorada

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$515

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: Pets allowed, Balcony or terrace

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Price per night from

$573

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$355

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$390

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

Islamorada villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$1,148

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

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$446

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: Pets allowed, Balcony or terrace

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Price per night from

$172

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$391

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$573

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$344

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Balcony or terrace

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Price per night from

$158

Great rentals within 20 miles that match your search

Private Key Largo Bayside Canalfront home

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$201

Key Largo Beautiful House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$264

Luxury 3-Bedroom Home with Resort Privileges

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$1,549

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

$344

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

$344

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 23 minutes

Match: Balcony or terrace Pets allowed

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Price per night from

$401

Waterfront Home In Florida Keys

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect Holiday in Tavernier” We had a wonderful time at Dan and Penny's home. They were very accommodating! The home is absolutely pristine and in a nice neighborhood. There wasn't a day that we did not see manatee and tarpon in the canal in front of the house. Perfect location for restaurants, shopping and activities either by land or water. Beautiful home with everything you need for a perfect vacation in the Keys!

Responds fast! avg. 1 hour 17 minutes

Match: Balcony or terrace Pets allowed

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Price per night from

$210

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Price per night from

$247

“Fantasic wedding on paradise!!” We picked Shadow Point because of it's fabulous secluded view and beautiful gardens on 2.5 acres. The house and cottage held up to 16 of us and was wonderfully decorated with period antiques. Our guests loved playing at their beach and kayaking and swimming around Key LargoSound. Our wedding was perfect with the full moon rising over our reception. We danced the night away in paradise.

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Price per night from

$2,405

Key Largo Rental Fantastic Views

Key Largo condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

Match: Balcony or terrace Pets allowed

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Price per night from

$401

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