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Vacation Rentals near Harry S. Truman Little White House

111 Front St, Key West, Florida 33040-8311
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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
    1/2 Block to Duval, World of its own -Nassau Suite1 / 17
    (33)Excellent
    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Best Location, 1/2 Block to Duval, Bimini Suite1 / 17
    (48)Very good
    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Center of It All - Paradise Island Suite1 / 56
    (31)Excellent
    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Steps to Duval, Old Town Charm -Grand Bahama Suite1 / 11
    (62)Very good
    0.2 miles from Harry S. Truman Little White House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    great location just off the main Duvall Street.the rooms are very well set-up with great decoration.the only issue was early morning noise from delivery trucks, especially...
    Reviewed 2 weeks ago
    Location was great, walking distance to everything. There was free parking at the house which was awesome. We enjoyed the pool. It was nice and clean. The out side area is...
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    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable...
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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Casa Havana1 / 24
    (3)Average
    0.2 miles from Harry S. Truman Little White House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Yard
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 17, 2018
    Location is the best. Casa Havana is 1/2 block off of Duval and 3 blocks from everything in Key West. Deck is great for drink and a cigar in the afternoon and having it own...
    Reviewed February 23, 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group...
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best...
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    Location Information
    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Truman Annex Shipyard with Tropical Garden1 / 8
    (3)Very good
    0.3 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Yard
    • Air Conditioning
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Overall pretty good place. Good location and parking 2 blocks from Duval Street. Too hot because A/C unit could only be run at 75deg F or it would lock up, causing a service...
    Reviewed August 9, 2017
    We love staying here. There was plenty of room and the condo was nicely decorated. We walked and biked all over with ease -- great location.
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    About this property
    Decorated in shade of sea foam and coral, this property is located in the Truman Annex and puts all of Key West's top attraction within easy walking distance. French doors open to a garden with hibiscus and cat palms framing a comfortable patio. Both bedrooms have queen beds, with a sofa bed in...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    0.3 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
    • Wi-Fi
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    • 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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    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
    0.3 miles from Harry S. Truman Little White House
    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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    Emma's Escape1 / 23
    (4)Excellent
    0.3 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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 Harry S. Truman Little White House
    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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    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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 Harry S. Truman Little White House
    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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    The Banyan Resort at Key West1 / 6
    (1)Excellent
    0.1 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Terrace
    • Internet Access
    • Outdoor Dining Area
    • Shared Yard
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.2 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,...
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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 Harry S. Truman Little White House
    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
    0.1 miles from Harry S. Truman Little White House
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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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    0.2 miles from Harry S. Truman Little White House
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy studio condo steps away to Duval Street action. MILE ZERO STUDIO (monthly rental): Here's a cozy spot for 1-2 people who are looking for comfort and convenience. Large studio has queen bed and sofa in the living space, full bath, and kitchenette that includes a microwave, dorm refrigerator...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Key West Charming1 / 23
    (26)Very good
    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 7, 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 December 2, 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
    Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental! KEY WEST CHARMING at the Shipyard Condominiums condo rental in Key West. This downstairs 2...
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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
    0.3 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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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    0.3 miles from Harry S. Truman Little White House
    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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    0.0 miles from Harry S. Truman Little White House
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Washer
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    • 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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    0.0 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Balcony
    • Terrace
    • Grill
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    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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    Duval Penthouse1 / 24
    (25)Very good
    0.2 miles from Harry S. Truman Little White House
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • DVD Player
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 11, 2018
    Great time! Will stay there again! People that can't sleep with noise shouldn't have the master bedroom, but it didn't bother us. We enjoyed having the bar next door for the...
    Reviewed February 18, 2015
    Love the Duval Penthouse; our second year staying there. Fantastic location, clean, well taken care of. Only one thing I would change... the mattress in the Master bedroom is...
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    About this property
    Location, location, location! Practically overlooking famous Duval Street from large upstairs deck! L DUVAL PENTHOUSE -- A large luxury vacation rental in Key West located in downtown Key West. This property has it all, fabulous location, beautifully furnished and plenty of space to accommodate...
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    Location Information
    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Shipyard Treasure1 / 26
    (53)Excellent
    0.3 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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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    The Mermaid's Garden1 / 24
    (1)Excellent
    0.0 miles from Harry S. Truman Little White House
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • 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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    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Terrace
    • Parking
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amazingly Perfect!!! That is how one of our guests reviewed Southard Getaway! This amazingly perfect rental can be yours as well! 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...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Sundown Refuge1 / 23
    (9)Excellent
    0.0 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 26, 2014
    We stayed here with family in Nov while attending a family wedding. The condo was a characterful, quirky place which had every facility required for a wonderful stay. It felt as...
    Reviewed March 2, 2013
    Location was great, easy walk to Mallory Square, Duval Street, Beach. Rent bikes, easy to ride to just about anyplace safe and quickly.
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    About this property
    View passing ships and sunsets from your own deck or balcony in the Truman Annex’s most prestigious building SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in Truman Annex. You'll...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Rose Treehouse1 / 20
    (7)Very good
    0.2 miles from Harry S. Truman Little White House
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Balcony
    • Washer
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 16, 2018
    This was a cute second story room with great windows and decks in the front and back. It was the perfect spot for our little get away for our 10 year wedding anniversary, as we...
    Reviewed November 14, 2017
    Stayed for 5 nights in October 2017. Great location on a small lane about 1/2 block to Duval. Cute place. Porches on front and back were awesome. Kitchen was well-equipped, and...
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    About this property
    Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed, one-full-bath studio that occupies the whole second floor with balconies off both the front and the...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    A Place In Paradise1 / 24
    (23)Very good
    0.2 miles from Harry S. Truman Little White House
    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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    0.3 miles from Harry S. Truman Little White House
    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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    Harbor Walk Hideaways1 / 44
    (20)Excellent
    0.3 miles from Harry S. Truman Little White House
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 11, 2016
    Our party of eight absolutely LOVED this place. Location was to die for and price could not be beat! Just steps from Sloppy Joes, The Green Room and Lagerheads Beach Bar just...
    Reviewed October 25, 2015
    My husband and I, and three other couples came to Key West for a friend's wedding. After much research, I am so thankful to have come across Harbor Walk Hideaways. The grounds...
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    About this property
    Very private gated compound sleeping eight guests right in the heart of Key West's Old Town. Enjoy the beat of Key West's nightlife, the romance of sunset at Mallory Square, or the excitement of deep sea fishing or water sports all less than a two-minute walk from our tropical paradise. Standing...
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    Location Information
    Key West, Florida Keys
    Private Room - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Key West home w/shared pool and just steps from historic Old Town1 / 24
    (1)Excellent
    0.2 miles from Harry S. Truman Little White House
    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
    0.0 miles from Harry S. Truman Little White House
    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 Harry S. Truman Little White House
    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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    0.1 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located one block off Duval Street in central Old Town, the unit is on a historic estate and renovated with modern conveniences, hardwood floors, and plantation shutters, with plenty of ambient light. This second story unit has a large bathroom and a large deck off the master bedroom for privacy...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Dolphin House1 / 23
    (3)Very good
    0.1 miles from Harry S. Truman Little White House
    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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    Bahama House1 / 24
    (27)Very good
    0.3 miles from Harry S. Truman Little White House
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Balcony
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 15, 2017
    Bahama House was a wonderful choice for a family gathering and week-long vacation in Key West. Its location in a quiet, short street, a block back from Duval Street, provided us...
    Reviewed April 13, 2015
    We spent Spring Break at the Bahama House and it was perfect for our group. We had 4 adults and 4 teens. Bedrooms were ideal, especially the upstairs room which could fit all...
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    About this property
    Luxury rental with all the amenities you can ask for, Bahama House might just be right right vacation rental for you! BAHAMA HOUSE - Location, Location, Location! Totally gorgeous, this spacious house rental Key West is conveniently located on a quiet street in the heart of Old Town Key West...
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    Location Information
    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    The Water's Edge1 / 25
    (2)Excellent
    0.2 miles from Harry S. Truman Little White House
    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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    Havana Hideaway1 / 25
    (22)Excellent
    0.0 miles from Harry S. Truman Little White House
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    • Washer
    • Balcony
    • DVD Player
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This was a great rental. It is beautifully decorated, within walking distance of everything, great View, very peaceful and quiet swimming area.My only complaint is the...
    Reviewed April 17, 2018
    My husband and I stayed at this condo with another couple. The location is absolutely the best and the condo itself was amazing. They had everything set up so you felt like...
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    About this property
    Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Crowner's Jewel1 / 24
    (35)Very good
    0.1 miles from Harry S. Truman Little White House
    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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    The Hemingway1 / 25
    (27)Average
    0.2 miles from Harry S. Truman Little White House
    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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    Banana Key1 / 25
    (8)Excellent
    0.0 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    • Air Conditioning
    • Washer
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Really nice space. I would rent again. Great location. Clean, you can easily have 4 people in this property.
    Reviewed July 25, 2018
    Banana Key is the perfect place to stay in Key West for 2 couples of a family of 4. Within walking distance to Duval St, piers, and a plethora of shops and restaurants. We never...
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    About this property
    Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Royal Palm1 / 25
    (4)Very good
    0.0 miles from Harry S. Truman Little White House
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 13, 2018
    This Foundry rental was very clean. The whole place was well maintained. The Foundry is a very spacious and quiet place to stay, close to everything but feels miles away when...
    Reviewed September 14, 2016
    Highly recommend this rental property. Located in a lovely quiet area but 5 minute walk to Duval Street. Fully equipped property could not have asked for anything more. Lovely...
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    About this property
    There's no better way to experience 'Island Time'-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    The Courtyard1 / 25
    (21)Very good
    0.3 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Parking
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 17, 2018
    Year before last we stayed here for six weeks; this year we stayed seven weeks. Next year we will again be staying seven weeks. For us, there is no better place to stay when in...
    Reviewed August 17, 2017
    100% our best rental place in Key West so far and we've been going for over 15yrs!Great location, nice pool, awesome to have a parking spot, secluded behind a gate. The cottage...
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    About this property
    Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs, and shade...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Foundry on the Waterfront ~ Weekly Rental1 / 20
    (2)Very good
    0.0 miles from Harry S. Truman Little White House
    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
    0.3 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Ann Street Gardens1 / 25
    (59)Very good
    0.2 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 28, 2018
    Where do I start? This little cottage is a hidden gem. Perfect for a couple! It was clean, comfortable, convenient and was equipped with everything you could possibly want...
    Reviewed July 26, 2018
    Absolutely wonderful. Just right for two people!!Loved our stay!! Literally steps away from the pool and right around the corner from Duvall St!! Had a great time!!
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    About this property
    (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens...
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    Location Information
    Key West, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    0.2 miles from Harry S. Truman Little White House
    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
    0.2 miles from Harry S. Truman Little White House
    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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