Vacation Rentals & House Rentals in Key West

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30 house rentals

Sunrise Waterfront Home

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Pool or snooker table Smoking allowed

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Price per night from

$488

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Blue Moon Tavernier

Tavernier house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Smoking allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$402

Coastal Key Largo Townhome with Ocean Views, Pool & Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Smoking allowed, Pool or snooker table

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Price per night from

$390

“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.

1 of 2 match: Pool or snooker table, Smoking allowed

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Price per night from

$316

Responds fast! avg. 3 hours 34 minutes

1 of 2 match: Pool or snooker table, Smoking allowed

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Price per night from

$1,606

Coconuts on the Water

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Pool or snooker table, Smoking allowed

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Price per night from

$206

1 of 2 match: Pool or snooker table, Smoking allowed

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Price per night from

$263

The Real Livaboard Experiance. Cruise Inciuded!

Key Largo yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Pool or snooker table, Smoking allowed

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Price per night from

$687

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Pool or snooker table, Smoking allowed

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Price per night from

$230

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Smoking allowed, Pool or snooker table

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Price per night from

$224

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Smoking allowed, Pool or snooker table

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Price per night from

$159

Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock

Islamorada villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Smoking allowed, Pool or snooker table

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Price per night from

$1,147

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Smoking allowed, Pool or snooker table

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Price per night from

$379

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 59 minutes

1 of 2 match: Smoking allowed, Pool or snooker table

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Price per night from

$545

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Smoking allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$623

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Smoking allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$668

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: Smoking allowed, Pool or snooker table

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Price per night from

$316

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Smoking allowed, Pool or snooker table

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Price per night from

$396

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Smoking allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$654

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Pool or snooker table, Smoking allowed

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Price per night from

$108

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: Pool or snooker table, Smoking allowed

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Price per night from

$134

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! :-)

1 of 2 match: Pool or snooker table, Smoking allowed

1 of 2 filters match

Price per night from

$215

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

1 of 2 match: Pool or snooker table, Smoking allowed

1 of 2 filters match

Price per night from

$2,122

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Pool or snooker table, Smoking allowed

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Price per night from

$1,031

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: Pool or snooker table, Smoking allowed

1 of 2 filters match

Price per night from

$688

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: Pool or snooker table, Smoking allowed

1 of 2 filters match

Price per night from

$344

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!

1 of 2 match: Pool or snooker table, Smoking allowed

1 of 2 filters match

Price per night from

$2,007

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

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pool or snooker table, Smoking allowed

1 of 2 filters match

Price per night from

$378

Charming House on deep clear canal

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 44 minutes

1 of 2 match: Pool or snooker table, Smoking allowed

1 of 2 filters match

Price per night from

$201

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

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

1 of 2 match: Pool or snooker table, Smoking allowed

1 of 2 filters match

Price per night from

$801

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