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Vacation Rentals near Fort Zachary Taylor Historic State Park

601 Howard England Way, Key West, Florida 33040-8395
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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Duval Balcony - Suite Mischief1 / 13
    (11)Excellent
    0.3 miles from Fort Zachary Taylor Historic State Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Truman Annex Shipyard with Tropical Garden1 / 8
    (3)Very good
    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Duval Balcony - Street Suite1 / 15
    (3)Very good
    0.3 miles from Fort Zachary Taylor Historic State Park
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Balcony
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 31, 2018
    Great location and great balcony overlooking Duvall St. This studio room was very clean and comfy. We will for sure stay again!!
    Reviewed March 6, 2017
    Tom was very nice and accommodating. He greeted us when we arrived. Great location in the heart of all the action of Duvall st and with this comes noise bring ear plugs for the...
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    About this property
    Located in the middle of Duval St, you are a 15 minute walk in one direction to the Atlantic Ocean and the Southernmost Point, and the same distance to the Gulf of Mexico and Mallory Square. Shopping, nightlife and the best restaurants are outside your front door. Hemingway House is 2 blocks away!...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.3 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations since I am not a real estate salesman or property manager allow me let the photos speak for themselves. My oversized two bedroom, one bathroom condominium is located on picturesque Southard...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (4)Excellent
    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    • Parking
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2018
    Great location!!! They supplied many extras beach chairs and beach towels. Loved that they had bikes right at the condo. We would definitely book this condo again
    Reviewed June 22, 2017
    Great place to stay. Wonderful amenities! Would highly recommend. Location is great for beach, Mallory square and Duval Street.
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table and...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Finn Key1 / 24
    (33)Very good
    0.1 miles 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
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 6, 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 February 10, 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
    Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat! 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...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Emma's Escape1 / 23
    (4)Excellent
    0.1 miles 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
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 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 February 6, 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
    Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street. 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....
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (57)Excellent
    0.2 miles 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 3 weeks ago
    This was the second time my family has stayed in this property. It is very well kept and the location can't be beat. It is furnished with everything you may need for a...
    Reviewed 4 weeks ago
    We had the best visit to Key West and this condo was perfect for the activities we were after. I was happy to see recent, positive reviews from others and had a great chat...
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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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • DVD Player
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 2 bedroom, 2.5 bath vacation rental. Enjoy the convenient proximity to most events Key West has to offer! 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...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Linger Longer1 / 23
    (22)Very good
    0.2 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Terrace
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 18, 2015
    I am a repeat renter and plan to return next year. Walking distance to everything but in a quiet community off Duval.
    Reviewed April 27, 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
    Just imagine stepping out of the rental and stepping right into the pool! Just relax and enjoy your vacation! 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...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Conch Haven Old Town 1/1 MONTHLY Rental1 / 12
    (2)Very good
    0.3 miles from Fort Zachary Taylor Historic State Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Patio
    • Washer
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 7, 2018
    We stayed in 1st level of 1863 house that has been updated extremely well; state of the art appliances, big & small--has complete sets of Cuisinart pots/pans, Fiesta Ware...
    Reviewed November 28, 2016
    This property is very convenient to everything in Key West. We walk every day--we can go to the beach, the sunset, Duval, and all of the various attractions on foot. The...
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    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Breezy Bungalow1 / 24
    (1)Excellent
    0.2 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Terrace
    • Parking
    • Balcony
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 20, 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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    About this property
    Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you! 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...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Alluring Porches1 / 24
    (17)Very good
    0.2 miles from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Terrace
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 31, 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 November 1, 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
    Beautifully decorated and spacious home in the community of Truman Annex is awaiting for you! 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,...
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy one of Key West's most desirable rental complexes, Truman Annex. Conveniently located just couple blocks to the beach, Duval Street and Mallory Square, makes this the ideal rental for a small family or couple of friends CONCH ADVENTURE - Nestled in a quiet corner of the Shipyard...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Walk Everywhere, A TRUMAN ANNEX CONDO! 2 PATIOS, POOL,WIFI,PARKING & BIKES1 / 33
    (11)Excellent
    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Balcony
    • Waterfront
    • Washer
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 1, 2018
    Nice 2nd floor condo with many amenities including bikes (4), beach chairs, & beach towels. Pack light and believe in karma :)
    Reviewed July 28, 2018
    Billy’s Blue Heaven was a fantastic place to stay! It was our first time in Key West and we couldn’t have asked for a better place to stay. It is in a great location, near...
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    About this property
    Billy's Blue Heaven is fresh, clean and Pristine. Just a two minute walk to Duval Street and only 300 steps to the world famous Ricky's Blue Heaven Restaurant. The balcony overlooks Truman Annex 's lush landscaping beside the shared swimming pool. A very short walk or bike ride to Fort Zachary...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Parrot Perch1 / 20
    (23)Very good
    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Parking
    • Terrace
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 18, 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 September 13, 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
    Unbeatable location! Only a block to famous Green Parrot bar yet in a secluded, quiet community of Truman Annex 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...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Siesta Bay1 / 25
    (3)Very good
    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Terrace
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 22, 2015
    At Home in Key West was nice to work with. We arranged everything via email. We reserved a smaller cottage, but when that was no longer available, At Home upgraded us to Siesta...
    Reviewed March 19, 2015
    This condo was fine. Nothing great but the location is terrific as it sits two short blocks off of Duval St. pretty much centrally located between the ends of the island. And...
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    About this property
    Here is your perfect opportunity to enjoy your stay in one of the most popular complexes of Key West, Truman Annex! SIESTA BAY -- Beautiful two bedroom one bath upstairs Key West condo rental in Truman Annex, just steps away from the shared pool and within walking distance of anything you'd...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.3 miles 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Celebration1 / 22
    (1)Very good
    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Parking
    • Balcony
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, recently updated 2 bedroom apartment located in a popular community of Truman Annex, only a short bike ride to Fort Zachary Taylor Beach SUNSET CELEBRATION: 2 bedroom 1 bath Shipyard condo located in Truman Annex. New floors, fresh paint, all new furnishings, artwork, linens and...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.2 miles from Fort Zachary Taylor Historic State Park
    4 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Washer
    • Balcony
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW This 4BR/1.5BA tropical retreat is situated in a lush gated community, enveloped by Spanish lime trees, hibiscus, orchids, and a wide variety of beautiful species and exotic palms. In a prime locale, you’ll be within minutes of everything Old Town Key West has to offer. Walk...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 10
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    0.3 miles from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Balcony
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island...
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    Location Information
    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.3 miles 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Shipyard Treasure1 / 26
    (53)Excellent
    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Terrace
    • DVD Player
    • Parking
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 2018
    This was our first time staying in the Truman Annex and was by far the best place we’ve ever rented in key west. I loved all the amenities including the pool, as well as how...
    Reviewed February 18, 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...
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    About this property
    Finding a perfect property for your family vacation is easier said than done, but this beautiful apartment might just be the one. SHIPYARD TREASURE: Contemporary Condo at Truman Annex - Walk to Beach/Duval Street Decorated in casual contemporary style, this second floor Shipyard condo is...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.3 miles 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    The Mermaid's Garden1 / 24
    (1)Excellent
    0.3 miles from Fort Zachary Taylor Historic State Park
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Washer
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    The Mermaid Garden is close to all of Key West's attractions yet nestled in a quiet historical location. The house has plenty of room, the kitchen has everything you might need...
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    About this property
    Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized brass mermaid sculpture installed in a garden bursting with tropical ferns and palms. A few...
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    Location Information
    Key West, Florida Keys
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    A Touch of Bermuda in Key West1 / 19
    (17)Excellent
    0.1 miles 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 October 9, 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 July 14, 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Emma's Secret1 / 22
    (1)Excellent
    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens. 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...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    A Place In Paradise1 / 24
    (23)Very good
    0.2 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 26, 2017
    The townhouse is in the perfect location. Close to everything. The community is very clean and quiet and the pool, albeit small, was great and just around the corner...
    Reviewed November 13, 2013
    I've been going to KW every year for about a decade and have learned that your home base for the week can be the difference between a good trip and a truly great trip. I've...
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    About this property
    Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE! A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in Truman Annex. One of the most desirable locations for vacationers, you will...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.1 miles from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Grill
    • Cable/satellite TV
    • 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West home w/shared pool and just steps from historic Old Town1 / 24
    (1)Excellent
    0.2 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Grill
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Internet Access
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly positioned rental with access to a shared pool puts you close to everything in Key West, so bring the whole family for a memorable tropical retreat. Situated in the premiere gated community of Truman Annex, this home is just steps from historic Old Town. The Truman Annex offers...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Truman's Hideaway1 / 24
    (11)Very good
    0.3 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Parking
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 12, 2013
    The house is old and vert worn. It needs upgraded paint and bedding plus nicer sheets and bath towels. The kitchen was fairly well equipped and adequate but could use updated...
    Reviewed December 12, 2013
    This property has a great location near Mallory Square and many attractions. Truman's Little White House is in your backyard! It needs a few updates and clean up in our opinion...
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    About this property
    Enjoy breathtaking sunsets with a glass of wine from your own private porch TRUMAN'S HIDEAWAY: It's hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. This lovely Truman Annex condo rental in the exclusive...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    President's Walk1 / 24
    (1)Excellent
    0.2 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Grill
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 4, 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
    Large outside deck invites you to just unwind after a long day of exploring with a good book and a glass of wine or enjoy it with friends grilling your fresh catch PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same location; now it's your turn....
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Dolphin House1 / 23
    (3)Very good
    0.2 miles from Fort Zachary Taylor Historic State Park
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 29, 2014
    The location is perfect for those that want a perfect mix of quiet but close to the action on Duval. The décor was beautiful, pool and outdoors perfect. Great area for grilling...
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    About this property
    Wonderful for larger groups or family get togethers, The Dolphin House offers a roomy vacation home in one of Key West's most desirable locations, Truman Annex. THE DOLPHIN HOUSE: Twice the comfort and twice the amenities - located in the exclusive Truman Annex. The Dolphin House Key West...
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    Location Information
    Key West, Florida Keys
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Top Of Duval- 6 Bedroom Penthouse1 / 26
    (14)Excellent
    0.3 miles from Fort Zachary Taylor Historic State Park
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 19, 2018
    This was such a perfect place for our group! All the suites are clean and large! The pool area was just perfect! You’re literally right in the middle of all the action of Duval...
    Reviewed April 7, 2018
    The location is perfect -- nearly equidistant from the Atlantic and the Gulf and in the midst of Duval Street restaurants, shops and bars. And, the rooms are great -- attractive...
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    About this property
    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual...
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    Location Information
    Key West, Florida Keys
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    The Water's Edge1 / 25
    (2)Excellent
    0.2 miles 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 March 6, 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
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.2 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Well maintained townhouse in the Truman Annex of Key West. The house has a beautiful garden that you will enjoy. A short walk to Duval and Mallory Square. All quality furnishings. Margaret' s Park is the choice in Key West. Two master suites with private balconies. The house is fully equipped...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
    • 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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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beach House Condo1 / 22
    (28)Very good
    0.1 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Parking
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 23, 2017
    First, let's talk about the positives. This is a two bedroom two bath unit on the end of a row in Shipyard Condominiums in Truman Annex. There is one reserved parking spot to...
    Reviewed April 13, 2015
    Lovely condo in a gated community! 5 min walk to pool, 8 minute walk to beach.Accommodations lovely and patio very nice. Centrally located, 2 blocks from Duval.A lovely spot...
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    About this property
    This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home. BEACH HOUSE CONDO: A beautiful 2 bedroom 2 bath ground level condo located in the gated Shipyard Condominium area of the prestigious Truman Annex community. You will find everything here you want...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Crowner's Jewel1 / 24
    (35)Very good
    0.2 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Terrace
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 18, 2017
    Stayed recently for a week and while the condo was clean and well maintained , and the location was great the showers were just way too small. There are two bathrooms upstairs...
    Reviewed November 5, 2014
    Great Place! 2 blocks from Duval. Spacious, great amenities. Showers are tiny but at least there are 2 which helps bigger groups get ready. Clean. Nice neighborhood.
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    About this property
    Imagine being able to walk to the Sunset Celebrations every single evening! Only couple blocks to Mallory Square you can find this true gem! CROWNER'S JEWEL: Experience the finest in vacation home rentals in Key West Florida when you stay in this delightful 2 bedroom 2.5 bath Conch-style...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 miles 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 Yard
    • 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Hemingway1 / 25
    (27)Average
    0.2 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Parking
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 17, 2018
    We had a wonderful week at the Hemingway last week! We loved the property and the location was just ideal! Someone said there wasn't WIFI but there is now.....Very comfortable...
    Reviewed March 22, 2015
    The property is located in a great convenient area. It is in close proximity to the beach , restaurants , shopping and entertainment.We enjoyed utilizing the rear deck each...
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    About this property
    The location does not get better than this! Short bike ride to the beach and walking distance to most restaurants and shops! THE HEMINGWAY -- A beautiful 2 bedroom 2 bath Florida Keys rental home located in the private, gated community of Truman Annex. An ideal location only 2 blocks from...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    HISTORIC KEY WEST - Turtle House - Sleeps 61 / 24
    (2)Excellent
    0.1 miles 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 June 22, 2017
    Spacious property with two pools, friendly neighbors and charming location just a short walk to all of old town Key West.
    Reviewed May 4, 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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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Poinciana House1 / 25
    (50)Excellent
    0.3 miles from Fort Zachary Taylor Historic State Park
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    My husband and I enjoyed our stay in the Poinciana House. The location couldn't be more perfect. It was close to central Duval, while still very quiet. We loved being across the...
    Reviewed July 29, 2018
    (Visited May 2015/2016)Our favorite place in Key West, great house located in Old town- in my personal opinion the best area to be- really good restaurants/bars (also not a...
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    About this property
    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging...
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    Location Information
    Key West, Florida Keys
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Foundry on the Waterfront ~ Weekly Rental1 / 20
    (2)Very good
    0.3 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 14, 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.
    Reviewed November 28, 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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    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 condominium, constructed within an important piece of historic American architecture. Situated along the gateway waterfront to...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 27
    (2)Excellent
    0.2 miles 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 June 22, 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 August 13, 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.2 miles 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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    Location Information
    Key West, Florida Keys
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Key West Casa1 / 24
    (26)Very good
    0.1 miles from Fort Zachary Taylor Historic State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Terrace
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 5, 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 June 12, 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
    This spacious 3 bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West most popular restaurants. KEY WEST CASA – Beautiful and spacious Shipyard condo Key West, Key West Casa is one of...
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    Location Information
    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Artist Garden1 / 24
    (27)Very good
    0.3 miles from Fort Zachary Taylor Historic State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 6, 2015
    We stayed at the Artist Garden for our triple birthday celebration (3 friends within a week). The house is beautiful. It is located within Truman Annex. And you can seriously...
    Reviewed April 10, 2014
    We enjoyed a 2 week stay in this beautiful house. The location is perfect. We were only a 5 minute walk to Mallory Square and a 10-15 min walk to other favorite restaurants. We...
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    About this property
    This spacious home with a large outside deck is tucked away on a quiet lane of Truman Annex, yet only a short walk to all events. Artist Garden makes an ideal vacation rental for those who like to enjoy Duval crawl and quiet peaceful vacation at the same time ARTIST GARDEN -- A bright and...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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