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Holiday Rentals near Fort Zachary Taylor Historic State Park

601 Howard England Way, Key West, Florida 33040-8395
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 80 Rentals in Key West
    Truman Annex Shipyard with Tropical Garden1 / 8
    (2)Excellent
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (4)Excellent
    0.1 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'. This two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch Plasma...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.3 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SOUTHARD GETAWAY: Imagine it. Arrive in Key West to a beach-like home in walking distance to all that Key West has to offer. Yes, that's Southard Getaway. Two queen bedrooms upstairs with full bath, open living space downstairs with quiet, shaded deck. Decorated in hues of blue and green that...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Key West Found1 / 24
    (32)Very good
    0.5 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Terrace
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2018
    This was a great vacation rental! My daughter got married in Key West and Key West Found was the perfect home for us to be close to venues, and of course all that Key West has...
    Reviewed 5 April 2015
    The Foundry in Truman annex is where I stay every time I vacation in KW- close to everything but quiet & peaceful for relaxation.
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    About this property
    KEY WEST FOUND – A striking Key West FL home for rent, this 2 bedroom, 2.5 bath townhome is located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. The...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Emma's Escape1 / 23
    (4)Excellent
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2013
    We have been staying at 717a Emma for four years now. We started for one month and next year, we'll be there for three. I think that this property has one of the most amazing...
    Reviewed 6 February 2013
    Once again we enjoyed our winter stay in Key West. The climate in the main attraction, but Key Westalso full of interesting people and places. The condo became a home away...
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    About this property
    Emma’s Escape (monthly rental): Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life. A fabulous location that will allow you to walk or bike to all the island highlights. In the heart of Old Town,...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Linger Longer1 / 23
    (22)Very good
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2015
    I am a repeat renter and plan to return next year. Walking distance to everything but in a quiet community off Duval.
    Reviewed 27 April 2014
    This was the first trip to Key West for my husband and I, but we traveled with more experienced Key West-ers who booked the rental. We were pleasantly surprised when we arrived...
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    About this property
    LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath home rental Florida Keys, located in the President's Walk of Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either side of the full bathroom on...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (55)Excellent
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    This is either the second or third time we've stayed here so that should tell you its quality. Beautiful condo with everything you need for a comfortable home away from home...
    Reviewed 26 May 2018
    Joanne and Jim were very nice and helpful! I loved the house and the location is superb! Beautifully furnished and comfortable. My only concern was the lack of hot water in...
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Garden Oasis is a first floor condo in the Shipyard Condos in Truman Annex. We are ideally located 2 blocks from the action (restaurants, shops, clubs) of Duval St., and very short walks to sunsets at Mallory Sq, and the beaches of Ft. Zachary Tayler Park. The Shipyard is a lushly landscaped...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Finn Key1 / 24
    (33)Very good
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2018
    I traveled with my best friend and her husband to Key West, and we decided on renting Finn Key for about a week. The location was phenomenal - we barely needed the car! We could...
    Reviewed 10 February 2016
    Lovely condo,great location, have stayed at Truman many times. Condo is clean and comfortable, neighbors upstairs must live here full time, they walk a little heavy but I...
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    About this property
    FINN KEY: A beautiful 2 bedroom 1 bath downstairs condo located in The Shipyard section of Truman Annex. This pristine residential community is one of the most requested locations in the heart of Old Town Key West. A wonderful mix of a private community yet easy walking distance to the Duval Street...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sunset Celebration1 / 22
    (1)Very good
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Balcony
    • Parking
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SUNSET CELEBRATION: 2 bedroom 1 bath Shipyard condo located in Truman Annex. New floors, fresh paint, all new furnishings, artwork, linens and towels. Be one of the first to stay in this totally updated vacation home. Master bedroom has queen bed and guest bedroom 2 twins on either side of...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    HISTORIC KEY WEST - Turtle House - Sleeps 61 / 24
    (2)Excellent
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Porch
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2017
    Spacious property with two pools, friendly neighbors and charming location just a short walk to all of old town Key West.
    Reviewed 4 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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    About this property
    OVERVIEW The Turtle House is a 100+ year old recently completely renovated historic 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. The house can be described...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.3 kilometres from Fort Zachary Taylor Historic State Park
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for a stunning four-bedroom, three-bath vacation retreat with its own private pool, you've found it at Island Style. Located in Truman Annex, Key West's signature gated community, this home has it all: 2,000 square feet in a compact two-story format, porches and balconies, deck...
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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.2 kilometres from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BOWE CONCH HOUSE (monthly rental): The Bowe Conch House has evolved within the Thomas family, Conchs, born and raised in Key West, for more than 4 generations. Prior to buying the house in the 1930's for $2,500, George and Ethel Bowe-Thomas lived across the street paying $3.00 per month for rent!...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Terrace
    • Parking
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CAPTAINS WHEEL: Take control of your vacation, be the master of your fate. Captains Wheel will not disappoint. Situated on the corner of Southard and Emma Streets in Truman Annex, a most prestigious gated community in the heart of historic Old Town. 2 bedrooms, 2.5 baths; each queen-bed room has...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Parking
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BAYVIEW HARBOR: “Bayview Harbor” is a beautiful, peaceful retreat ideally located on Southard Street, walking distance to the beach at Fort Zachary Taylor Historic State Park, Duval Street and Mallory Square. This unique property is newly renovated to provide the perfect island retreat together...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Bahamian Reed1 / 24
    (1)Average
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2017
    This is a middle townhouse unit in the Truman Annex section of Key West. The photos are a true representation of the unit. One bedroom had a king; another had two twins...
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    About this property
    BAHAMIAN REED: 2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West. Conveniently located near all the reasons you came to Key West: Fort Zachary Taylor State Park , Duval Street shops, galleries, bars and restaurants, and Sunset Celebration. Gourmet kitchen, bright...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    HISTORIC KEY WEST  - Conch House - Sleeps 51 / 21
    (4)Excellent
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Porch
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 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...
    Reviewed 22 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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    About this property
    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 environment - (1) queen bed, (2) twin...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Parrot Perch1 / 20
    (23)Very good
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    • Terrace
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2016
    This unit was in a great location, clean and well laid out. Couple of things we noticed since we have stayed in other condos in the Truman. The WiFi was very poor in strength...
    Reviewed 13 September 2013
    Very nice condo for two couples. Clean & comfortable. Walking distance to Duval and most of the sights in Key West. Nice pool area. Overall a Great experience!Just a couple...
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    About this property
    PARROT PERCH -- Located in the gated Shipyard Community in prestigious Truman Annex, this condo in Key West is in a great location and a great value for a great vacation. Parrot Perch is an upstairs 2 bedroom 2 bath condo with a balcony from the living room offering a view of the neighborhood....
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    A Barefoot Retreat1 / 24
    (1)Very good
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
    • DVD Player
    • Terrace
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A BAREFOOT RETREAT: Step into this fantastic condo and the first thing you'll want to do is take off your shoes; feels just like home. Located on the main entry to Truman Annex, an exclusive gated community in historic Old Town, with all that Key West has to offer in easy reach: Duval Street with...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CONCH ADVENTURE - Nestled in a quiet corner of the Shipyard Condominiums in Truman Annex, this 2 bedroom 1 bath downstairs condo offers peace, quiet and convenience. Within steps of the road to Fort Zachary Taylor State Park in one direction and to the community pool in the other direction. Just...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 54
    (2)Excellent
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Porch
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2017
    We have stayed here 2 or 3 times. It is small, but there are just 2 of us and our dog. Works for us! Very cute and cozy. Washer & dryer. Compound is quiet and...
    Reviewed 13 August 2016
    The Cigar House has one the best location you can expect in Key West, close to Fort Zachary, Hemingway's House or Duval St. and all its attractions.This lovely house is full of...
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    About this property
    OVERVIEW The Cigar 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 four (4) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (1) queen...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Emma's Secret1 / 22
    (1)Excellent
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Emma's Secret (Monthly Rental) Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life. A fabulous location that will allow you to walk or bike to all the island highlights. In the heart of Old Town,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Truman Annex Irish Condo Innisfree1 / 33
    (5)Excellent
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2016
    This was my 2nd time staying in the Shipyard section of the Truman Annex. Each time was in a different 2BR condo. this condo was clean, well equipped with kitchen, bath...
    Reviewed 24 January 2016
    I attended college at a later age and upon graduation took 2 friends and my sister to Truman Annex for a 10 day vacation!!! We had the best time. As a matter of fact I am back...
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    About this property
    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.4 kilometres from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Historic Preservation Award Winner! This licensed vacation home was recently featured on Key West's historic home tour and is available to rent monthly. We recently completed a massive 6-month remodel, making this one of the more spectacular vacation homes you'll find for rent in Old Town. In...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Breezy Bungalow1 / 24
    (1)Excellent
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Terrace
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    Great location - within walking distance of Duval Street, Mallory Square, Hemmingway House, and many other attractions that we visited. The Truman complex, where it is located...
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    Breezy Bungalow - Weekly Rental When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside breezes to flow openly into Breezy Bungalow. Two levels of...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Key West Casa1 / 24
    (26)Very good
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2017
    We just recently returned from our stay in Key West Casa. This condo has everything you need. We did not use the bikes because we did not know how to unlock them, but we never...
    Reviewed 12 June 2016
    We stayed in Key West Casa and absolutely loved that property. It is a 3 bedroom, 2 bath with a porch, back patio, balcony. The kitchen is fully equipped, one of the best we've...
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    About this property
    KEY WEST CASA – Beautiful and spacious Shipyard condo Key West, Key West Casa is one of only a few 3 bedroom 2 bath condos in the Shipyard complex. This great rental property is located in the prestigous Truman Annex community just 2 blocks to famous Duval Street and walking distance to shopping,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    City Cay1 / 22
    (3)Excellent
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Balcony
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2017
    We stayed for a week at City Cay. The location could not have been any better. The condo was supper clean and well maintained. We would definitely stay here again! It is a one...
    Reviewed 1 August 2016
    We loved City Cay. It was a small condo with one king bed, a futon and a small kitchen, but it was exactly what we needed. The bed was super comfortable. The bathroom was...
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    About this property
    CITY CAY: Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This lovely Truman Annex Condo is the place! City Cay is our 1-bedroom 1-bath upper level condo that has been lovingly renovated and furnished in a sleek modern style of the most hip urban...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.3 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This amazing penthouse condo has one of the best view in Key West. Located in historic Mills Place in the main part of Truman Annex, you have the views of the Gulf and ships that pass by the windows as they arrive and leave port. The apartment has four exposures and three of them with balconies....
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.5 kilometres from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.5 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Balcony
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Townhome, 2 Bedrooms, 2.5 Baths, (Sleeps 4) Available for weekly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful gated Truman Annex community. It’s close to all the major attractions yet just far enough away to be quiet and relaxing. Duval Street,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.3 kilometres from Fort Zachary Taylor Historic State Park
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Terrace
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West is like a little piece of the Caribbean at the lowermost point of the United States: it’s reliably warm, the waters are a gorgeous turquoise, and it is a small, intimate community. From this second floor condo it’s just a short walk to Mallory Square’s sunset celebrations, the Ernest...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    A Touch of Bermuda in Key West1 / 57
    (17)Excellent
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2017
    By the time you arrive, you will already feel like you are part of Jack's family. He will literally bend over backward to accommodate you. We have vacationed in Key West for...
    Reviewed 14 July 2017
    I stayed in Jack's condo (a touch of Cuba in Key West) this past week and we enjoyed every aspect of it. The condo is two bedroom one bath and was perfect for my party of three...
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    About this property
    Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is just past the...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    HISTORIC KEY WEST  - Main House - Sleeps 101 / 47
    (4)Average
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Grill
    • Balcony
    • Washer
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 28 November 2011
    I rented The Main House at Bahama Gardens for a family vacation of about 10 days over Thanksgiving. There were 5 of us, myself, my husband, two adult sons and one son's...
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    About this property
    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 ten (10) guests - (1) queen bed, (1) full bed, (1)...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Alluring Porches1 / 24
    (17)Very good
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2018
    Everyone in our group loved the place. It was clean and well stocked with about anything you need. A porch off both bedrooms and a small, secluded deck that was perfect. It's...
    Reviewed 1 November 2015
    Everything as advertised and more. Immaculate, tastefully decorated, roomy. Close to Duval. Porches on each bedroom and off living room. Huge master bedroom with large porch...
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    About this property
    ALLURING PORCHES - A beautiful 2 bedroom 3 bath townhome with an additional den, is the tranquil escape you have been looking for. Wonderfully decorated with Key West charm and unique art work, stunning orchids surround this home and a beautiful open air feel brings the outside in while you just...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.4 kilometres from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    President's Walk1 / 24
    (1)Excellent
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    This place was perfect for the three adults and infant. The proximity to the pool, Duval St., and Green Parrot really made this beautiful condo ideal for a long Key West trip...
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    About this property
    PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same location; now it's your turn. President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind. Situated directly in front of one of the community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lavender Jungle1 / 24
    (27)Very good
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    My husband and I stayed here last week and was very pleased! We would definitely stay here again in the future and we would recommend this place to anyone. Great location...
    Reviewed 4 weeks ago
    Perfect spot. Literally walking distance to the beach to the water park to Duval street to everything . The front had a porch and the back had a deck with a grill and table. Two...
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    About this property
    LAVENDER JUNGLE - Beautiful 2 bedroom 1 bath downstairs Shipyard condo for rent Key West located in Truman Annex, this home has a renovated kitchen and upgraded bathroom. For those who don't want to climb stairs, this property is on the first floor and has a large brick patio and grill. Master...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Conch in Training1 / 20
    (6)Very good
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Secure Parking
    • Air Conditioning
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2017
    Walking distance to practically everything. Mallory Square, Fort Zachary Taylor, beach, Duval st., grocery store, Hemingway house, and Southernmost point. I stayed for a week...
    Reviewed 14 June 2017
    Great location in the heart of Truman Annex. Re-modeled condo w/updated appliances. Minutes from Fort Zach Beach and Southernmost Beach. Green Parrot, Blue Heaven and...
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    About this property
    (The Shipyard Owners Association has informed us that the parking area will be closed during AUGUST 2018 for repaving (subject to change) so there will be no parking available during this period. If you wish to book for August 2018 please contact our office directly.) The name of this one-bedroom,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Water's Edge1 / 25
    (2)Excellent
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2017
    The house was gorgeous, and the sunset view from the balcony lived up to expectations... Short walk to Duval Street... Totally recommended
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    About this property
    Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.5 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find the utmost in beauty and convenience at this two-bedroom Key West home, a light-filled escape with a private patio, a heated community pool, and an ideal location close to beaches, nightlife, restaurants, and historic sites. You'll find this elegant home in the Truman Annex neighborhood of...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    0.4 kilometres from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Balcony
    • Internet Access
    • Parking
    • Hot Tub
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If Key West is on your travel itinerary, make this lovely rental for six your home away from home and spend your time lounging by your private pool and spa. Located in Historic Bahama Village, this home is one block away from the world-famous Duval Street, where you can enjoy galleries, shops,...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    0.5 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Parking
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find the utmost in beauty and convenience at this two-bedroom Key West home, a light-filled escape with a private patio, a heated community pool, and an ideal location close to beaches, nightlife, restaurants, and historic sites. You'll find this elegant home in the Truman Annex neighborhood of...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    0.5 kilometres from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A sun-soaked getaway in the Florida Keys awaits you when you stay at this beautiful dog-friendly vacation rental! Lounge in comfort by the private pool or stay inside and enjoy the air conditioning while you browse the cable channels on the flatscreen TV. However you spend your vacation days,...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shipyard Treasure1 / 26
    (52)Excellent
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Terrace
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2015
    Shipyard Treasure is welcoming, comfortable, condo, decorated with Key West art in the bedrooms, living room, and entry, and with wonderful beds, bedding, and much better than...
    Reviewed 16 March 2013
    My family had a wonderful vacation while staying at the Shipyard Treasure. The condo was tastefully decorated and was stocked with all the comforts of home. The location was...
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    About this property
    SHIPYARD TREASURE: Contemporary Condo at Truman Annex - Walk to Beach/Duval Street Decorated in casual contemporary style, this second floor Shipyard condo is centrally located in the Truman Annex, within quick walking distance to all the sites and attractions of Old Town Key West. Relax in 2...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.5 kilometres from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Terrace
    • Wi-Fi
    • Grill
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lighthouse Villa: This timeless private conch home just steps away from the Hemingway House and the Key West Lighthouse a perfect location to be close to great restaurants and shops. The tropically inspired three level home offers privacy separating your entertaining spaces from your tranquil...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Key West Charming1 / 23
    (26)Very good
    0.3 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2016
    The location was awesome, close to everything. We loved that it was close to Blue Heaven. The condo was too small for our liking, but that's not to say that it isn't...
    Reviewed 2 December 2013
    this was a great condo and the location was perfect for the boat races. very clean and everything was just as stated.no problems at all!! and @home in key west were great...
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    About this property
    KEY WEST CHARMING at the Shipyard Condominiums condo rental in Key West. This downstairs 2 bedroom 1 bath home has been lovingly cared for by the owners. They actually use the property themselves each spring so they know what will make their guests stay more comfortable. The living and...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Contemporary beachside escape with shared pool and close to local attractions1 / 25
    (4)Very good
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Parking
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2014
    We had a wonderful time staying in Key West. The condo location was perfect. We walked everywhere. The beds were comfortable, and although the kitchen is very small, it was...
    Reviewed 12 March 2014
    This place is a very nice place to stay.Key West Vacation Rentals are very helpful and easy to reach.The location is perfect just 5 minutes walk to Duval Street and 15 min to...
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    About this property
    Grab your sunglasses, bathing suit, and sunscreen and get ready to dive into the beach lifestyle when you book this Key West condo. Boasting a shared pool to stay cool, this home gives you the chance to slip into vacation mode with ease. This condo is just two blocks from Fort Zachary Taylor...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sunny tropical condo with a shared pool, close to all of the beachside action1 / 28
    (5)Very good
    0.2 kilometres from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Parking
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 November 2012
    Arrived with spouse and our 2 adult children. This condo was clean, had all the amenities that we could have hoped for. Nice quiet neighborhood, yet close to Duval St...
    Reviewed 6 February 2011
    Close to Duval St, and Mallory Square - within a 10 min walk with small kids. Amenities were great - kitchen, washer/dryer, family room. Access to pool. Looking forward to a...
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    About this property
    Boasting a great location in the Truman Annex, a shared pool, and easy beach access, you won't have to go far to dive into the beachside fun! Less than a mile to the picturesque Mallory Square and just under a mile to Fort Zachary Taylor Historic Park, there will be no shortage of attractions to...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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