Houses Key West

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59 houses

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

Match: Rental types Shared outdoor pool (heated)

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Price per night from

$344

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Shared outdoor pool (heated)

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Price per night from

$1,146

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Rental types Shared outdoor pool (heated)

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Price per night from

$1,146

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Rental types Shared outdoor pool (heated)

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Price per night from

$1,488

HISTORIC KEY WEST - Main House - Sleeps 8

Key West house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“February visit to Key West” Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!

Match: Rental types Shared outdoor pool (heated)

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Price per night from

$2,063

Match: Rental types Shared outdoor pool (heated)

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Price per night from

$614

Noah, Family Ocean Paradise

Key West house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types Shared outdoor pool (heated)

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Price per night from

$1,336

Lighthouse Suites Collection Duval St. and Pool

Key West house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 20

Responds fast! avg. 1 hour 30 minutes

Match: Rental types Shared outdoor pool (heated)

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Price per night from

$2,863

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Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$492

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$167

Sombrero Reef Lighthouse Suite Duval St. and Pool

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$430

Sunshine suit (2/2 apartment)

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$524

Key West Lighthouse Suite Duval St. and Pool

Key West cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$401

Tortugas Harbor Lighthouse Suite Duval St. and Pool

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$430

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$343

Alligator Reef Lighthouse Suite Duval St. and Pool

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$687

A Change in Latitudes - TRUMAN ANNEX

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$172

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

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$321

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: Rental types, Shared outdoor pool (heated)

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Price per night from

$488

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!

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$435

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

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$465

Artist Cottage

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Key West, Spring 2012” In a word,our stay with you was ”wonderful”. We have been to Key West on several occasions and have loved every visit. Staying in Truman annexe was even more special. We all felt like we were at home with everything we needed. You must feel blessed to live in that part of the world. We will be looking for a job for our 19 year old son,Tom. He wants to come and work over in Key West. We have just arrived home and everything seems grey, and much colder than Key West. Depending on finances( the pound-dollar rate is not too good just now) we hope to come back soon. We will definitely be giving you a call.I would recommend your accommodation and company to future holiday makers. Love and blessings John,Jayne,Jack and Tom

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$380

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great condo” Great condo - nicely decorated and most well stocked kitchen ever. Everything was so neat and clean and there was an abundance of supples. Would highly recommend

Responds fast! avg. 1 hour 58 minutes

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$320

1 of 2 match: Rental types, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$488

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

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$918

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

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$107

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$155

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: Rental types, Shared outdoor pool (heated)

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Price per night from

$342

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Rental types, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,948

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

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$915

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!

1 of 2 match: Rental types, Shared outdoor pool (heated)

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Price per night from

$659

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: Rental types, Shared outdoor pool (heated)

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Price per night from

$344

The Mermaids House, Historic Old Town Key West

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

1 of 2 match: Shared outdoor pool (heated), Rental types

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Price per night from

$328

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: Shared outdoor pool (heated), Rental types

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Price per night from

$134

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: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$2,122

Olivia Place

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$344

Beautiful Home Located In Quiet neighborhood

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$340

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$268

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