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Key West House Rentals

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$382
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$216
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1 Bedroom, 4 Bathrooms, Sleeps 2
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$440
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1 / 27
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$256
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1 / 26
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Studio, 1 Bathroom, Sleeps 2
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  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Brand New to the Rental Market! Part of Banana's Foster Guest House This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go... View all property information
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5 of 5 stars Reviewed 12 November 2014
This place was perfect for what we were looking for: Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
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$382
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1 / 30
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Each suite is furnished with kitchen, contemporary & comfortable living room furniture, new ultra comfortable mattresses... View all property information
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5 of 5 stars Reviewed 17 December 2014
My wife and I stayed at this location during Fantasy Fest. It was our first time at Fantasy Fest but we are Key West regulars. The rooms are newly remodeled, clean and well...
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$986
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1 / 29
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4 Bedrooms, 4 Bathrooms, Sleeps 10
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Elder access
  • x
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About this property
This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is... View all property information
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$216
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1 / 24
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Internet Access
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
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  • Wheelchair access
  • Elder access
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  • x
About this property
What a unique way to spend time on the water. Its not a 5 star hotel but you will have a nice clean private chartered boat on the water. Get ready for a unique vacation that others will envy. Boat is a 2003 Beneteau 331, while the boat is dockside the marina has electricity, water and Internet.... View all property information
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5 of 5 stars Reviewed 5 March 2014
I grew up sailing, so I knew what to expect for accommodations on the 33 foot Beneteau. It has everything you could possibly need, in a slightly smaller version. One couple...
5 of 5 stars Reviewed 24 February 2014
The boat is exactly as stated and I found the accommodations very pleasant and comfortable . We stayed three nights. However some people might not as there are very "tight...
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$1,294
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1 / 23
5 Bedrooms, 4 Bathrooms, Sleeps 14
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Amenities & Details
  • Air Conditioning
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
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About this property
Just behind the curving waterfront of Key West's picturesque harbor lies the 19th century Historic Seaport District of this once great trade center. It is here where grand wooden homes, such as the Grand Marshall Key West -Bahama Estate,were built by original seafaring merchant's.Today these... View all property information
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4 of 5 stars Reviewed 14 September 2011
I stayed as part of a large group of girlfriends celebrating a birthday. The house is located on a wonderful residential street. We rented all 3 units that make up the Grand...
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$370
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1 / 19
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Internet Access
  • Sauna
  • Shared Outdoor Pool...
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
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From
$986
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1 / 15
4 Bedrooms, 4 Bathrooms, Sleeps 10
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  • Air Conditioning
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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About this property
In this case... 'Two is definitely better than One'! A rare set of early 1900's 'twin-cigar maker's cottages' perched on the southern end of famous Duval Street. The Twice As Nice  vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge... View all property information
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5 of 5 stars Reviewed 5 November 2012
House decorated nicely and very well maintained. Great pool and above average accommodations. Close enough to walk to everything at Mallory Square if you like a little exercise...
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From
$801
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1 / 29
3 Bedrooms, 3 Bathrooms, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
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About this property
Key West Vacation Rental 'SECRET VILLA' A Hidden Jewel in Historic Old Town Key West Location, Location, Location....This amazing property is situated on a quiet and peaceful lane away from traffic and noise. The secret location is also just a few blocks from everything Key West has to offer;... View all property information
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5 of 5 stars Reviewed 26 September 2014
Secret Villa had everything our group of 7 (3 married couples and 1 single) was looking for to celebrate my wife's 40th birthday. Comfortable, well-appointed, clean, great...
5 of 5 stars Reviewed 25 July 2014
Stayed here a week with 2 other couples. GREAT LOCATION. 1/2 block to the food store (Fausto's food palace) and liquor store, 1 block to Walgreens (on Duval - one block away...
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From
$462
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1 / 9
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50', 42', and 27' flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home... View all property information
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5 of 5 stars Reviewed 29 May 2013
Hemingway's Retreat was more than we could have hoped for! The house was beautiful, the location was perfect, and the pool was awesome for our family. The owner was fantastic to...
5 of 5 stars Reviewed 4 January 2013
Recently I spent a month at the property. It was well taken care of and Mark was very responsive to our needs. The home was well set up and then some. The pool is very private and...
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From
$863
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1 / 24
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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About this property
As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere... View all property information
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5 of 5 stars Reviewed 9 April 2014
We rented this 4 bedroom 3 bath house for vacation with our adult children, 6 month old grandson and 87 year old father. It was perfect! One bedroom downstairs for Grandpa, a...
5 of 5 stars Reviewed 11 March 2014
We loved the privacy and security of the house. All family members enjoyed the quiet time at the house and the party atmosphere within walking distance. We had day trips and...
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$351
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1 / 14
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2 Bedrooms, 1 Bathroom, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
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  • Wheelchair access
  • Elder access
  • x
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About this property
SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Conch House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open sociable living... View all property information
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5 of 5 stars Reviewed 1 July 2014
My husband & I found the Conch House online. The property manager, Craig, met us upon our arrival and was very friendly. Throughout our trip, he was very helpful and very...
5 of 5 stars Reviewed 23 June 2014
This property is so beautiful and peaceful.!! Perfect location, 2 short blocks from Duval, 1 block from Ft. Zach beaches. We stayed in the Conch House , We could not have been...
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From
$8,318
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1 / 21
3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
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  • ?
About this property
NEW ONE OF A KIND UNIT! To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially transformed into Old... View all property information
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From
$493
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1 / 25
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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About this property
You'll know you've found island heaven--the term heaven meaning transcendence or going beyond the ordinary--when you enter Casa Camilla. This two-bedroom, two-bathroom home located in the lovely Meadows neighborhood of Old Key West is extraordinary inside and out. The outside rear half of the... View all property information
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5 of 5 stars Reviewed 6 August 2014
the house was clean and roomy. two couples had plenty of space and we enjoyed the pool and kitchen. we will definitely be back.
5 of 5 stars Reviewed 3 April 2014
Our week at Casa Camilla was wonderful. We called Key West Liquors to order wine before we left home. They were courteous, reasonable and it was there waiting for us to...
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From
$233
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1 / 13
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Resort style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amidst lush tropical landscaping, sits Island Style, the sister cottage of Hidden Treasure. One of our most popular properties, it was renovated by two fabulously funky sisters who share... View all property information
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4 of 5 stars Reviewed 10 July 2014
Nice little cottage with private patio, located adjacent to the pool. Cottage was clean and well maintained, and had a full kitchen with all the amenities. It was walking...
5 of 5 stars Reviewed 23 December 2012
Kevin, Shelby, and all the folks at KW Hideaways, I wanted to take a moment to thank you all for a wonderful experience! You and your team worked hard to ensure everything...
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From
$228
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1 / 5
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features which will help make your stay in Key West special. It is located in a wonderfully private... View all property information
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5 of 5 stars Reviewed 9 December 2014
This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at...
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From
$253
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1 / 12
1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
• Wireless Internet • Full Kitchen Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs tiled... View all property information
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4 of 5 stars Reviewed 19 August 2014
This small townhouse was absolutely the most convenient thing we could have asked for in Key West. 1/2 block off Duval Street at Truman. We literally parked the car and walked...
5 of 5 stars Reviewed 6 May 2014
I was in town for a wedding, and decided to get a rental home instead of an overpriced hotel. The place was the perfect size & location was incredible! The courtyard was quiet...
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From
$1,066
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1 / 25
5 Bedrooms, 6 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
THE VICTORIA HOUSE - This gracious historical property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis Johnson. It is located just three blocks from Duval Street, in the heart of Key West’s Old Town, within walking distance of restaurants, shops,... View all property information
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From
$704
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1 / 17
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4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Main House is a (2) story 100+ year old, recently completely renovated Conch house. The design of this property lends itself perfectly to small gatherings of families and friends. The house can comfortably accommodate a maximum of eight (8) guests - (1)... View all property information
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4 of 5 stars Reviewed 11 July 2014
This property is lovely. With the large main house and several small cottages,it would be great for family reunions. The pool, jacuzzis and landscaping are all beautifully...
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From
$616
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1 / 17
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Turtle House is a 100+ year old recently completely renovated Conch house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas.... View all property information
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5 of 5 stars Reviewed 5 May 2010
The best place to have a taste of old Key West. Not at all like anything you would rent anywhere else in the country!It was walking distance to everything in Old Town and the...
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From
$1,848
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1 / 40
10 Bedrooms, 6 Bathrooms, Sleeps 20
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
THIS ISN'T JUST A HOUSE, THIS IS YOUR OWN PRIVATE MINI RESORT IN KEY WEST, FLORIDA. THIS IS THE PROPERTY USED BY MTV TO FILM THE 2006 REAL WORLD KEY WEST. 500 FEET OF OCEANFRONT, 8 to 10 BEDROOMS are available (sleeps up to 20) , 5 1/2 baths, 11 plasma TVs, pool table (and Ping Pong), tennis... View all property information
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5 of 5 stars Reviewed 4 May 2014
We, 14 girls from la, stayed at the MTV House for 1 week and enjoyed it very much. The house is located in a quiet neighbourhood 10 minutes from town which is nice in contrast to...
5 of 5 stars Reviewed 1 May 2014
My family (20 total multiple generations) rented this property out for our children's Spring vacation time. We were very pleased with our stay. The property location is wonderful...
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From
$709
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1 / 13
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
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  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Very private gated compound right in the heart of Key West's Old Town. Enjoy the beat of Key West's nightlife, the romance of sunset at Mallory Square, or the excitement of deep sea fishing or water sports all less than a two-minute walk from our tropical paradise. Standing outside the gate, on... View all property information
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5 of 5 stars Reviewed 13 December 2014
Our forth time in Key West and this is the best location and value you could ask for. It's not fancy but has everything you need, it makes you feel like you are on an island. All...
4 of 5 stars Reviewed 16 September 2014
I just celebrated my 30th in this lovely place. We rented all the villas : 2 1-bedroom & 1 2-bedrooms. There were 9 of us. We used the grill available for my birthday luau...
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From
$351
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1 / 18
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
  • x
About this property
FOR INSTANT PRICING, go to KeyWestYachtandBreakfast.com. Most nights require 3 night minimum but email or call us if you want less and we can negotiate a fair rate. Upscale 'Yacht and Breakfast'! 3 bedroom, 4 bed, 2ba luxury yacht. Fully equipped from bow to stern -- Galley (kitchen to the... View all property information
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From
$431
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1 / 27
3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Satellite TV
  • Shared Outdoor Pool...
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The M/V Coconuts is a completely unique home with 360 degree water views, it also happens to be a 50-foot trawler, permanently docked at the Key West Harbor Marina. This is more than a boat. It really is a very comfortable home, with proper living area, bedrooms and large sundecks. There is over... View all property information
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5 of 5 stars Reviewed 3 December 2014
My family and I, all seniors, wanted to spend 3 days in Key West, but not in a sterile hotel setting. By George we found it. From the moment we rented the M/V Coconuts till the...
5 of 5 stars Reviewed 27 July 2014
My daughter opted out of her high school senior week beach trip and requested a unique family and friend experience. Wow, did the M/V Coconuts Provide!!! We had 5 kids, 2x19...
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From
$370
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1 / 32
3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Satellite TV
  • Shared Outdoor Pool...
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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About this property
Come stay aboard our FABULOUS houseboat Libra! Docked in one of Key West's most exclusive yacht club marinas, our guests have free access to a host of 'members only' amenities including a swimming pool, private beach, tiki bar, fitness facility, sauna, clubhouse, onsite restaurant, free parking and... View all property information
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5 of 5 stars Reviewed 16 August 2014
We just spent 2 days in the Libra in Key West and what a fantastic stay. Ray is awesome, very helpful and allways available, he cooks also in the New York Pasta Garden and it will...
3 of 5 stars Reviewed 24 April 2014
we were on this boat for 3 nights. Before we were 2 nights on the Coconut boat. We liked the Coconut more because it is more cozy, but that is of course our personal thoughts...
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From
$610
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1 / 25
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
  • x
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About this property
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two... View all property information
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5 of 5 stars Reviewed 17 April 2014
This house was gorgeous. Clean, updated and simply beautiful. It also had everything we needed...hair dryers, ironing board, laundry room, etc. If you are looking for something...
5 of 5 stars Reviewed 10 October 2013
Six women stayed in this beautiful townhome for three nights for a girls getaway. We would normally have booked hotel rooms, but staying here far exceeded our expectations and we...
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From
$104
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1 / 36
3 Bedrooms, 3 Bathrooms, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
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About this property
28 NIGHT MINIMUM STAY REQUIREMENT - THE STUDIO AT THE SAILMAKER'S HOUSE Beautifully Renovated Second Floor Studio for Two - Incredible Location in Historic Old Town Gorgeous studio apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located... View all property information
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5 of 5 stars Reviewed 3 September 2014
I really enjoyed my stay at the sailmaker's studio. The staff as well as the owner were very easy to work with and very helpful. My small dog was with me and he enjoyed it too. It...
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From
$6,839
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1 / 9
2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
If you have ever had the fortune to wander the historic streets and lanes of Key West's famous seaport neighborhood then you know how time seems to stand still. Yet right in the heart of Key West's bustling seaport this blissfully ideal cottage-style house offers all the amenities one could desire... View all property information
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From
$980
Per Night
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1 / 37
3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
The Absolute Best Luxury Private Weekly Vacation Rental Home on Duval Street In Old Town Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find... View all property information
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4 of 5 stars Reviewed 18 December 2014
This house is wonderful. Beautiful, clean and centrally located. We stayed for 10 nights and although the grill never worked, the rest of the house was as perfect as the other...
5 of 5 stars Reviewed 25 September 2014
Look no further! This home is simply incredible. The home itself is immaculate with every amenity you could ever need. This has be be the best location in all of old town Key...
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From
$462
Per Night
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1 / 14
3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
This is for the guest that would like to experience the yachting lifestyle without ever leaving the dock. Staying at the dock allows you to come and go as you please whether it be scootering around town or shopping, eating and drinking your way down the famous Duval St. You may just want to stay... View all property information
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4 of 5 stars Reviewed 21 February 2014
Three couples shared the Quest and had a wonderful time! Staying on the boat added a quirkiness to our adventure that really suited us. Coffee with the sunrise & cocktails with...
5 of 5 stars Reviewed 4 February 2013
If you ever wondered what it would be like to spend time on a yacht of your own, here is your opportunity! My husband and I along with 4 of our friends enjoyed our days on the...
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From
$244
Per Night
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1 / 20
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • ?
  • Wheelchair access
  • Elder access
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About this property
Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair completes... View all property information
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5 of 5 stars Reviewed 9 October 2014
Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
5 of 5 stars Reviewed 19 August 2014
My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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From
$431
Per Night
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1 / 9
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Relax in paradise amongst all the comforts of home in the Sailor House, a proud member of Andrew's Garden Cottages. Just one block from the main inn, and a half a block off the world famous Duval Street, the Sailor House offers the ultimate in privacy and luxurious island living. This prime... View all property information
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5 of 5 stars Reviewed 10 July 2014
I went down to Key West with my husband, 2 year old son, and baby sitter. This cottage was perfect for us. The bedrooms (both upstairs) were comfortable and both had great...
5 of 5 stars Reviewed 14 June 2014
We had never stayed in downtown Key West before and were a little anxious that there would be too much craziness going on to be able to rest. What a pleasant surprise that...
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From
$616
Per Night
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1 / 11
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Studio, 1 Bathroom, Sleeps 2
Booking
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  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
****************************Minimum One Week Stay ********************************************** My place is located less than a 15 walk from the beach. No need for a car when you are close to everything on the island. You are going to LOVE Key West! This is a small but very comfortable cottage... View all property information
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From
$370
Per Night
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1 / 12
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
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About this property
Just as you're inspired by an island oasis, so is this tropical Island Oasis Garden Home vacation rental. Cleverly hidden in the heart of Old Town Key West, this small private gated oasis uses a traditional Key West style architecture of tin roofs, wooden planking, sash windows, and charming front... View all property information
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5 of 5 stars Reviewed 13 September 2014
Can't say enough of this home. The home is in a secure gated community with 13 total townhomes. A pool is the center of the complex with homes around the pool. The area was...
5 of 5 stars Reviewed 17 August 2014
Beautiful, two bedroom condo in a secluded oasis. Yet close to all the sights off Duval. Clean, well kept. Thoroughly enjoyed our stay. Highly recommend!
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From
$244
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1 / 24
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Part of 4 exclusive units at Abbey Road, renovated January, 2010, this free standing historic cottage at 918-920 Center Street, features a king pillow-top bed, 2 lushly padded swivel chairs and a full kitchen which includes a full stove, refrigerator with ice-maker, microwave, dishwasher and soft... View all property information
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5 of 5 stars Reviewed 3 September 2014
Really enjoyed this place. Pics are accurate as this place looks in great condition. Loved the patio/hot tub area, also the use of the pool just across the street and grill...
5 of 5 stars Reviewed 12 March 2014
We absolutely loved Harrison's Hideaway. It was in the perfect location - 1/2 block off of Duval, a very short bike ride to the beach. It was immaculate, too - must have been...
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From
$308
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1 / 25
1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
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About this property
This delightful one-bedroom, one-bath conch cottage is set back from White Street, which runs the fourteen-block width of the island from the Gulf of Mexico to a fishing pier jutting out into the wide Atlantic Ocean. The street, named after Colonel Joseph White, memorializes a bit of Key West... View all property information
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5 of 5 stars Reviewed 8 October 2014
My wife and I have made several trios to Key West but we decided to stay in a house for this trip, and we couldn't have been happier to find this gem. The house was better than...
4 of 5 stars Reviewed 6 August 2014
This is a perfect cottage for two people. Located in a quiet part of Old Town but only 10 minutes walk from all the excitement of Duvall Street. Garden and swimming pool were...
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From
$367
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1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West. It features every high end amenity that you... View all property information
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5 of 5 stars Reviewed 29 October 2014
Hidden Treasure is just that - a hidden treasure located off of Olivia street in The Colony. Lots of space including storage, a great outdoor area, a quiet secluded area and yet...
4 of 5 stars Reviewed 12 September 2014
Great location for walking and biking all around Key West. Close to restaurants and attractions. Limited Parking.
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From
$5,669
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1 / 7
2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
This gentle Governor's Retreat in the Key West Meadows is an immaculate luxury vacation rental cottage ideal for a quiet couple or single person with discerning taste. The property is the perfect Key West setting for rest, relaxation, and rejuvenation. It is ideal for the person of distinction who... View all property information
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From
$739
Per Night
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1 / 19
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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About this property
Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major renovation to become the premium Penthouse on Duval. Just completed in June, 2009, this unique private Caribbean style penthouse is the perfect prescription for some lofty relaxation. Perched... View all property information
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4 of 5 stars Reviewed 18 December 2014
My friends and I rented the penthouse on Duval for a Bachelorette party and it was truly amazing! The house was so gorgeous inside that we all felt like we were on an episode of...
5 of 5 stars Reviewed 16 October 2014
I rented this house located in the PERFECT spot on Duval street for my Bachelorette party. I was plenty of space for all of us and the house was beautiful. Came with everything we...
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From
$370
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1 / 8
2 Bedrooms, 1 Bathroom, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
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  • Wheelchair access
  • Elder access
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About this property
Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this Secret Courtyard Cottage hideaway, you'll never know you're right in the center of Old Town Key West. Situated at the end of a little walking lane, this charming cottage is made completely private... View all property information
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5 of 5 stars Reviewed 18 July 2012
This house was great, it is a tad small but if your ok being in close quarters to split with some people its absolutly perfect. I traveled to Key west with my boyfriend as well as...
3 of 5 stars Reviewed 14 February 2011
This should be a great place on the face of it. The cottage, at 512 Petronia, is ideally located - 100m from Duval (but just far enough away for it to be very quiet), very...
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From
$219
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1 / 19
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1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Part of TROPICAL VILLAGE Tropical Hideaway - Lush gardens surround this lovingly restored two-story vacation house. This downstairs rental cottage has one bedroom with full bath and features a living room with queen sleeper-sofa, cable TV, DVD, stereo with CD player, and wireless internet. The... View all property information
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5 of 5 stars Reviewed 15 November 2014
I booked our condo through VRBO based on location and price. What a great find. Perfect location to Old Town activity and only a mi,e leasurely walk to Mallory Square and the...
4 of 5 stars Reviewed 9 October 2014
Everything was great! The location was perfect - and the private hot tub was the best! Only down side (which wasn't a big deal) was there were ants on the kitchen counter! Very...
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From
$431
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1 / 9
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Key West cottage architecture has been thoroughly 'time-tested' in 'island life and culture' in this somewhat infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.' Since its original construction in the early 1900's this note-worthy Cockadoodle... View all property information
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From
$307
Per Night
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1 / 29
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Ahoy! PirateHead Cove, your affordable vacation dream-come-true is now taking bookings for 2013/14! We are located within Key West city limits in one Key West's only waterfront neighborhoods. We are about 4 miles from Duval Street and downtown, about 2 miles from Smather's Beach and the... View all property information
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From
$170
Per Night
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1 / 30
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Studio, 1 Bathroom, Sleeps 4
Booking
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Part of Southernmost Sanctuary Suites The Heron Suite is located street side with it's own porch for people watching. Get one of Ana's Cuban mixes - it just doesn't get any better! Conveniently located to the beach, Duval Street, great restaurants, Ana's for great Cuban fare and morning coffee -... View all property information
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4 of 5 stars Reviewed 29 July 2014
Located right by the Southernmost Hotel and a block off Duval this was a great stepping off point for fun in Key West. Cuban market on the corner for café con leche each morning...
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From
$370
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1 / 7
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during... View all property information
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5 of 5 stars Reviewed 2 December 2013
We just stayed here Thanksgiving week and had a great time. It is right off Duval Street and you can walk any where easily. The hot tub is the back yard is very private. The...
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From
$2,218
Per Week
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1 / 8
2 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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About this property
Located in one of Key West's most striking gated waterfront luxury neighborhoods, Foundry on the Waterfront vacation rental provides a unique opportunity to enjoy a modern luxury condominium constructed within an important piece of historic American architecture. Situated along the gateway... View all property information
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4 of 5 stars Reviewed 15 May 2014
The condo was very comfortable and in a great location in being able to walk about anywhere. The only item from the 5th star is the matteresses could be replaced.
5 of 5 stars Reviewed 29 November 2011
This unit was in the perfect location to experience Duval Street and Mallory Square. Close walking distance to everything and yet just far enough away so you do not hear the...
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From
$1,879
Per Night
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1 / 31
7 Bedrooms, 7 Bathrooms, Sleeps 16
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
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About this property
Grande Dame Key West – (The Watson House) vacation rental estate is an impeccably detailed 3-story Classic Folk Victorian home with 7 bedrooms and 7 bathrooms. An award winning renovation of this stately Victorian mansion has achieved an impressive balance of timeless charm, classic elegance, and... View all property information
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5 of 5 stars Reviewed 17 December 2014
We stayed here as a large group on a birthday getaway in December. We had both houses rented for a total of 11 bedrooms and 11 bathrooms. The fact that every bedroom comes with...
5 of 5 stars Reviewed 9 December 2013
This was our second stay at the Watson House. First was in November, 2010. We were very pleased to see the owners had done extensive remodeling to the property. Every bedroom...
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From
$22,181
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1 / 42
5 Bedrooms, 6 Bathrooms, Sleeps 12
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
  • ?
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About this property
Perfectly positioned on Sunset Key, ‘the islands island,’ the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the ‘main island’ of Key West. A splendid view gazing toward Mallory Dock and the famous sunset celebration, this one-of-a-kind waterfront property offers a... View all property information
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