Vacation Rentals & House Rentals in Florida Keys

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85 house rentals

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

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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$446

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$907

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$907

Cabanas Key Largo Unit 3

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 15 minutes

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$172

Florida Keys Beach Home Pool Fishing Diving

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful stay” Post hurricane and still a spectacular place to stay. Office staff was great. Free use of tennis court, rackets, and balls. Pool and jacuzzi were very excellent. TG

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$2,282

Responds fast! avg. 3 hours 34 minutes

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$1,597

Private and comfortable four bedrooms, three bath, private oasis

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

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$320

WAKE UP to your NATURE SPOT on the OCEAN

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 24 minutes

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$205

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

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$343

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

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$516

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$970

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Bay and Beach Beauty

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 10 minutes

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Price per night from

$530

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$113

The Real Livaboard Experiance. Cruise Inciuded!

Key Largo yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 4

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$686

Spacious 1 Bedroom, Full Kitchen, Central Air, Beach, Marina and Docks

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“Tranquil and friendly” This was a place we found after months of searching and having another owner cancel out on us. We came in with a pre judgement of the place and BOY were we wrong. Everyone is super nice, everyone there(employees and guests) are very caring and friendly. The apartment was very comfy and well equipped, although anextra blanky or throw would have been nice to have for the sofa lounging. We are only 4 days into it but all is great!

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$280

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$280

1 Bedroom, Full Kitchen, Mini Split Air, Beach and Marina Apt #1

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$280

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$314

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$280

Boaters Dream House in the Water with 175’ of Sea Wall

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$770

Spacious 1 Bedroom Duplex, Full Kitchen, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 25 minutes

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$281

Island Conch Cottage

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$154

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$3,993

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Price per night from

$262

Responds fast! avg. 2 hours 25 minutes

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Price per night from

$365

Moveable Feast

Key West house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$430

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!!!!

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$133

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Price per night from

$571

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

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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$314

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$343

Modern house in the heart of Key Largo

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$343

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

$1,466

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

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$315

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.

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Price per night from

$172

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.

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$86

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.

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$485

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$107

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.

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Price per night from

$157

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