Vacation Rentals & House Rentals in Key West

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24 house rentals

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. 2 hours 26 minutes

Match: Swing set or jungle gym Secure parking

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Price per night from

$602

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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: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$161

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: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$464

A Change in Latitudes - TRUMAN ANNEX

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$172

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$228

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$378

Yellow vacation home, water view, boat dock, heated private pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$476

Lobster Lagoon

Stock Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$974

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$5,720

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$395

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: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$344

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: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$379

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: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$107

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$1,946

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: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$342

Florida Keys at it's best

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$241

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

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$315

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: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$800

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: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$492

Noah, Family Ocean Paradise

Key West house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$1,334

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$1,140

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: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$659

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$911

1 of 2 match: Swing set or jungle gym, Secure parking

1 of 2 filters match

Price per night from

$911

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