Vacation Rentals & House Rentals in Islamorada

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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

Match: Jacuzzi or hot tub Towels provided

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Price per night from

$984

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Jacuzzi or hot tub Towels provided

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Price per night from

$574

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Jacuzzi or hot tub Towels provided

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Price per night from

$392

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Price per night from

$2,132

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

Islamorada villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Jacuzzi or hot tub Towels provided

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Price per night from

$1,148

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Jacuzzi or hot tub Towels provided

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Price per night from

$391

Islamorada cottage on deep water canal

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Jacuzzi or hot tub Towels provided

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Price per night from

$287

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

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Jacuzzi or hot tub Towels provided

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Price per night from

$1,492

mojito breeze getaway, islamorada

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

Match: Jacuzzi or hot tub Towels provided

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Price per night from

$516

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Manatee Bay

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

1 of 2 filters match

Price per night from

$262

Windley Key, FL Keys

Islamorada caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$115

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$230

Keys Kottage

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$316

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$459

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$804

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: Jacuzzi or hot tub, Towels provided

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Price per night from

$254

Experience the Florida Keys like never before!!!

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$246

Beachfront Islamorada Villa with Dockage and Bay Views

Lower Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$349

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$603

Islamorada Waterfront Townhome w Priv. Beach! Comfortable Family Vacation Rental

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$603

Vacation in Tropical Paradise with the Family! Waterfront Townhome in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Jacuzzi or hot tub, Towels provided

1 of 2 filters match

Price per night from

$603

1 of 2 match: Jacuzzi or hot tub, Towels provided

1 of 2 filters match

Price per night from

$603

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, Towels provided

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Price per night from

$574

“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

1 of 2 match: Jacuzzi or hot tub, Towels provided

1 of 2 filters match

Price per night from

$672

Islamorada Waterfront Paradise 2

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$517

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$356

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, Towels provided

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Price per night from

$409

Paradise at Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$161

Townhome in Beachfront Community: Perfect for Florida Keys Vacation!

Islamorada townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$660

Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

1 of 2 filters match

Price per night from

$603

Islamorada Townhome w/Beach View, Pool, Marina,Tennis! Perfect Family Getaway!!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

1 of 2 filters match

Price per night from

$204

Perfect Family Getaway! Waterfront Vacation Home in Islamorada, Florida Keys!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

1 of 2 filters match

Price per night from

$660

Remodeled Townhome in Waterfront Community - 20% for Spring/Summer!

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Towels provided

1 of 2 filters match

Price per night from

$603

Boater's Paradise

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Jacuzzi or hot tub, Towels provided

1 of 2 filters match

Price per night from

$378

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

1 of 2 filters match

Price per night from

$345

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Towels provided

1 of 2 filters match

Price per night from

$458

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Towels provided

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Price per night from

$159

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, Towels provided

1 of 2 filters match

Price per night from

$1,475

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