Vacation Rentals & House Rentals in Key West

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84 house rentals

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Children's pool Iron

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Price per night from

$343

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Iron

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Price per night from

$158

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Harbour Dream~3/2..DKKB24~McGinnis

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 17 minutes

1 of 2 match: Children's pool, Iron

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Price per night from

$671

Coconuts on the Water

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Children's pool, Iron

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Price per night from

$205

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Iron

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Price per night from

$457

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Iron

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Price per night from

$446

Beachfront Islamorada Villa with Dockage and Bay Views

Lower Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Iron

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Price per night from

$347

Hammerhead Hideaway- 2 Bed 2Bath Canal Front Home w/Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Iron

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Price per night from

$341

The Butterfly Cottage

Marathon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Iron

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Price per night from

$251

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Iron

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Price per night from

$327

Outstanding Oceanfront Condo on the Beach!!

Marathon condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$341

Islamorada cottage on deep water canal

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$286

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Matecumbe Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

“Relaxing Weekend Getaway” We love this home! It is on a private dead-end street, and everything is just perfect. Kept the boat right at the dock, fished right there at night, took some nice boat rides through the back country, and relaxed in paradise. Wifi is good and fast (I had to do some work while we were there), and we can't wait to go back.

1 of 2 match: Children's pool, Iron

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Price per night from

$172

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: Children's pool, Iron

1 of 2 filters match

Price per night from

$571

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Children's pool, Iron

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Price per night from

$619

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: Children's pool, Iron

1 of 2 filters match

Price per night from

$978

1 of 2 match: Children's pool, Iron

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Price per night from

$559

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Children's pool, Iron

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Price per night from

$498

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great condo” Great condo - nicely decorated and most well stocked kitchen ever. Everything was so neat and clean and there was an abundance of supples. Would highly recommend

Responds fast! avg. 1 hour 58 minutes

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$319

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Iron

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Price per night from

$354

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$485

Islamorada Waterfront Paradise 2

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$514

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$388

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: Children's pool, Iron

1 of 2 filters match

Price per night from

$337

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$456

"Gulfside Grouper", Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK

Marathon Shores house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$978

Conch House - Dock Your Boat

Little Torch Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$770

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

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$1,483

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$514

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

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$685

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$257

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$407

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$3,993

Waterfront Anchor House with Boat Basin and Ramp!

Little Torch Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$754

3Bd/2Ba POOL on Canal, Dock, Kayaks, Bikes, Fishing Poles, Sombrero Beach 2.3mi

Marathon Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$571

Lower Keys PARADISE 200 Ft of Dockage, Heated Pool, Quick Atlantic Access

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 24 minutes

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$400

Key Colony Beach-2 Bed 2 Bath Canal Front Home with Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$306

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Iron

1 of 2 filters match

Price per night from

$514

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