Vacation Rentals & House Rentals in Florida Keys

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79 house rentals

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 48 minutes

Match: Games room Safe

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Price per night from

$107

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Games room Safe

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Price per night from

$395

Oasis Canal-Front Home: Pool, 30ft Dock, BBQ, and more!

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Games room Safe

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Price per night from

$516

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Welcome to Paradise

Long Key townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Safe, Games room

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Price per night from

$206

Conch House - Dock Your Boat

Little Torch Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Safe, Games room

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Price per night from

$775

Paradise at Moon Bay!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Safe, Games room

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Price per night from

$229

mojito breeze getaway, islamorada

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Safe, Games room

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Price per night from

$514

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Safe, Games room

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Price per night from

$224

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: Safe, Games room

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Price per night from

$230

Tropical Island Getaway-Keys

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Games room

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Price per night from

$337

1 of 2 match: Safe, Games room

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Price per night from

$819

Sunset Water Views! Moon Bay Key Largo Remodeled Condo with Boat Slip!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Games room

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Price per night from

$315

Bay and Beach Beauty

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Games room, Safe

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Price per night from

$533

Island Conch Cottage

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Games room, Safe

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Price per night from

$155

Cabanas Key Largo Unit 3

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 15 minutes

1 of 2 match: Games room, Safe

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Price per night from

$172

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

1 of 2 match: Games room, Safe

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Price per night from

$134

1 of 2 match: Games room, Safe

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Price per night from

$574

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Games room, Safe

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Price per night from

$316

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Games room, Safe

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Price per night from

$345

Modern house in the heart of Key Largo

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Games room, Safe

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Price per night from

$345

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Games room, Safe

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Price per night from

$976

Private and comfortable four bedrooms, three bath, private oasis

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Games room, Safe

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Price per night from

$322

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: Games room, Safe

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Price per night from

$343

1 of 2 match: Games room, Safe

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Price per night from

$488

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: Games room, Safe

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Price per night from

$173

Beautiful Private Home with Beach Access

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Great place for a family” Wonderful place to stay! My family of 5 enjoyed the clean rooms and full kitchen. Easy access to private beach, restaurants, grocery store. Very safe neighborhood. The house was fully provided for our stay, Great access to John Pennycamp and the Everglades. We would definitely stay here again. Daniel A. was very easy to work with. We enjoyed coming home after a busy day of snorkeling to make supper and lounge on our own deck or wander down to the private beach to enjoy the evening. Having this home made our vacation very relaxing and enjoyable.

1 of 2 match: Games room, Safe

1 of 2 filters match

Price per night from

$87

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

1 of 2 match: Games room, Safe

1 of 2 filters match

Price per night from

$488

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Games room, Safe

1 of 2 filters match

Price per night from

$108

Florida Keys Splendor at Hammer Point

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Winter Paradise!” My wife and I stayed at this great place in January 2014 and it was wonderful. It was very clean and well maintained. The canal was great to watch the fish jump and we saw Manatees almost every day. We especially liked the kayak and did a lot of site seeing from the ocean side. Migdy was great to work with and very accommodating. We would highly recommend this place to anyone.

1 of 2 match: Games room, Safe

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Price per night from

$158

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 52 minutes

1 of 2 match: Games room, Safe

1 of 2 filters match

Price per night from

$984

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Games room, Safe

1 of 2 filters match

Price per night from

$342

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

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Games room, Safe

1 of 2 filters match

Price per night from

$1,492

Private Key Largo Bayside Canalfront home

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Games room, Safe

1 of 2 filters match

Price per night from

$201

Key Largo Beautiful House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Games room, Safe

1 of 2 filters match

Price per night from

$264

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: Games room, Safe

1 of 2 filters match

Price per night from

$689

1 of 2 match: Games room, Safe

1 of 2 filters match

Price per night from

$373

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Games room, Safe

1 of 2 filters match

Price per night from

$409

Responds fast! avg. 3 hours 34 minutes

1 of 2 match: Games room, Safe

1 of 2 filters match

Price per night from

$1,607

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