Vacation Rentals & House Rentals in Key West

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79 house rentals

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

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$316

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$2,008

Harbor Walk Hideaways

Key West b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$1,303

Key West House

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$689

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Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$161

Sunshine suit (2/2 apartment)

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$525

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$493

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$167

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$343

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$402

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$402

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$430

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$687

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$430

A Change in Latitudes - TRUMAN ANNEX

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$172

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$482

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$614

Lighthouse Suites Collection Duval St. and Pool

Key West house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 20

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$2,863

One-bedroom time share suite in the heart of Old Key West

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 26 minutes

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$339

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$859

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$345

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$322

Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$840

BOOK MARGARITAS IN PARADISE KEY WEST LUXURY MONTHLY CONDO BEST VALUE

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$382

Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$458

Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$478

1 of 2 match: Private outdoor pool (unheated), Swimming pool

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$107

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$488

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

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$344

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$380

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$1,147

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!!

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$2,066

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$1,147

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$1,492

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$342

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