Vacation Rentals & House Rentals in Key West

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104 house rentals

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$107

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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$912

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 2 hours 7 minutes

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$342

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$485

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with chairs for all 6 of us. My husband enjoyed watching March Madness on the large T.V. Kathy did a fantastic job with all communications and provided great tourist tips. We would definitely stay here again!

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$656

Key West Island Vacation

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 8 minutes

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$478

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

$2,111

Shipyard-1/2 Block Duval Street

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

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$229

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect location and great value!” From the moment we arrived, this condo was everything we wanted without breaking the bank. We spent days looking for a place in Key West for Christmas week. What was available was crazy expensive, so to be honest when we found this place for the price we were slightly apprehensive. It is close to everything, the check-in and check-out were easy, the people who live in the complex were very friendly and welcoming and always willing to offer advice on where to go and what to do. Everything worked and was clean and we could not have asked for a better vacation. Can't wait to go back!

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$433

"Little Paradise" Historic Seaport Old Town Key West

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$490

Irish in Truman Annex Shipyard close to Historic Duval & Ft Zach State Park

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$571

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$913

Truman Annex-Steps to Famous Duval Street

Key West townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 38 minutes

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$392

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 14 minutes

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Price per night from

$286

Atlantic Paradise Found modern luxury Best pool in Key West fine finishes

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$1,369

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$742

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$1,140

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!!!

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$343

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

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$340

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Key West Adventure” We were two couples on our first visit to explore the keys. The condo was nice for four people. Not fancy but adequate. Could use a little updating to make it nicer. Located quite aways from Duval atreet and the action. Uber costs about $20 one way to get downtown. Too far to walk. The pool was amazing. No complaints.

Responds fast! avg. 2 hours 41 minutes

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$320

Henry's Piece Of Paradise On The Ocean In Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“nice place” Accommodations were nice Good view Henry was great to work with

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$462

Key West Affordable Ocean View Condo. Clean priced well on the Atlantic

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$742

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$1,369

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$1,140

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$1,141

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$970

“The perfect place to stay in Key West” This property is just 1 block off Duval -- but closer to the quiet, quaint side. I was so impressed with the accomodations -- fully equipped! We could have stayed there a month! The grounds are beautiful, lush, tropical and quiet. Staff was super friendly -- it is also very private with a large locking wrought iron gate keeping the units apart from the street -- we loved everything about it! We will stay here again on our next visit for sure!~

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$793

Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$856

Olivia Place

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$343

Ocean Front Key West Oasis Island Tones Charming Historical Downtown area

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$761

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Price per night from

$907

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

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$200

Private, heated pool. Private yard.

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$172

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$1,482

Ocean View Monthly Rental at 1800 Atlantic- Open Nov, December & January

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$172

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$1,141

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$907

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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Price per night from

$133

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