Houses Florida Keys

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341 houses

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!

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Price per night from

$574

Home w/Gourmet Kitchen- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$639

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!

Responds fast! avg. 2 hours 56 minutes

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Price per night from

$327

Expertly Decorated-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$579

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$688

“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

$2,408

Clean & Pristine Home - Marina Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$639

Hidden Gem Sunset Views-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,369

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$1,849

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

Boutique Resort w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$639

4 Bd w/Pool, Bayside - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$1,849

Family Friendly w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$579

Attn:Couples, 3 Kings - Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$579

Terrace & Roof Top Deck-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$579

Roof Top Water Views - Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$639

Gated w/Bayside Marina- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$639

Couples Getaway, Suites-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$579

Private Island Rental with 19' Boat, Seabird Key

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Heaven On Earth!” From the moment you step foot on this beautiful island paradise, you'll feel like you've been transported to your own little private world! Every amenity has been thought of from an outstanding outdoor kitchen, complete with state of the art grill, oven and microwave along with dinnerware, glassware etc. Not to mention the kitchen inside the house comes complete with all you need also. Even spices, just not food! The house itself is amazing and has a awesome stereo system so you can have music in the house, on the decks and on then beach! You can snorkel, swim, fish, sail, canoe, kayak, go tubing walk along the perfectely maintained tropical paths. From sunrise to sunset you day will be filled with beautiful scenerey, The view from the front porch is my favorite, I could sit there all day and have! This was our 7th trip and we had a extended stay of 10 glorious days, also our first trip with friends who loved it as much as we do! We've spent my birthday and our anniversary (back to back) here many of times and there is no place else we would rather be! The island is alive with hermit and land craps and Iguanna's and birds of all sorts. It's so funny to see a hermit crap go by with some sort of object he found as a shell. At night when you turn all the outside lights on it's like a magical transformantion! I can not say enough good things about Seabird Key. The owners and care takers do such a amazing job! Thank you for sharing this tropical paradise with us and we hope to be back again soon!

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Price per night from

$2,007

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$630

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$4,014

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$401

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$630

Boater's Paradise

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$378

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$1,432

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

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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 31 minutes

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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 31 minutes

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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 31 minutes

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Price per night from

$573

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$458

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$1,432

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$630

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$859

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

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$573

Blue Fish Point: Tranquil, Luxurious Waterfront Oasis, Amazing Sunsets, Pool, Ti

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$174

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$630

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$327

The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dock

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$144

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