Vacation Rentals & House Rentals in Florida Keys

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148 house rentals

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$108

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,032

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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$689

Royal Palm House

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Beautiful Home in Marathon” We truly loved this place, the home was clean, spacious and very comfortable! My husband still claims to this day that was the best sleep he has had in years and that's a big compliment coming from him! We loved having water access (although we didn't have a boat) it really made for some beautiful sunsets and sunrises! We found a couple of amazing restaurants that we visited on several occasions, the first and our favorite was Tarpon Creek following as a very close second was The Sunset Grill and Raw Bar, also our favorite breakfast spot became Juice Paradise Cuban Cafe (the best coffee). I'm only just now getting around to reviewing this place because we are planning another trip to the Keys in December and I was checking this place out and i didn't see our review and ask my husband about it (I thought he posted it and he thought I posted it), so finally 2 yrs later I'm giving our review!!! Unfortunately I see it's booked for our time frame and we are very disappointed about that but I know whoever booked it WILL NOT be disappointed! Thanks so much for an amazing experience, Gina & Scott PS we actually stayed Sept 2014 but it would only let me go back to Oct 2014! :-)

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$215

Sunrise Waterfront Home

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$488

Charming House on deep clear canal

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 44 minutes

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$201

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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$134

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

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Price per night from

$801

Eleanor's Place in Key West Old Town - Dogs Ok

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$514

Coconuts on the Water

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

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$206

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$263

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“Perfect” Great house. Very clean and simple. You share the beach and dock with the two other houses in the property but was never an issue. Location is great in Largo. Martha was a great host and very friendly. Will definetly be going back.

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$316

Responds fast! avg. 3 hours 34 minutes

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Price per night from

$1,607

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$230

The Real Livaboard Experiance. Cruise Inciuded!

Key Largo yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$686

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Key West house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

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Price per night from

$2,123

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

$2,004

Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min.

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

1 of 2 match: Pets allowed, Smoking allowed

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Price per night from

$344

Bay Pointe

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$204

Blue Lagoon

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$318

Casa Turquesa

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$288

Island Time 1 (half of duplex)

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$141

Island Time 2 (half of duplex)

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$148

Breeze Swept

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$268

Lafitte Landing

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$144

Manatee Bay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$151

Margarita Villa

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$189

Island Time (both halves of duplex)

Big Pine Key house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$236

Pirate's Cove

Cudjoe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$118

Villa Cayo

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$414

St. Croix

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$121

Coral House

Ramrod Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

Island Chalet

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$161

Conch Out

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$194

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$208

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$155

Private, heated pool. Private yard.

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

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$167

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