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Holiday Rentals near Harry S. Truman Little White House

111 Front St, Key West, Florida 33040-8311
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Center of It All - Paradise Island Suite1 / 14
    (31)Excellent
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Best Location, 1/2 Block to Duval, Bimini Suite1 / 17
    (48)Very good
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Steps to Duval, Old Town Charm -Grand Bahama Suite1 / 11
    (60)Very good
    0.4 kilometres from Harry S. Truman Little White House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    1/2 Block to Duval, World of its own -Nassau Suite1 / 17
    (32)Excellent
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Grill
    • Washer
    • Outdoor Dining Area
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2018
    We stayed in the Nassau suite at the Bahama house and found it perfect for everything we needed. The rooms were clean and the location was ideal. I will definitely book the...
    Reviewed 15 July 2018
    Just returned from a three night stay in the Bahama House Nassau Suite I’ve the 4th of July. Stayed with another couple and thoroughly enjoyed the suite. Equipped with all of...
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    About this property
    The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an endless party, The Nassau...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Truman Annex Shipyard with Tropical Garden1 / 8
    (3)Excellent
    0.5 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days 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 9 August 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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    Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (4)Excellent
    0.5 kilometres 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 21 April 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 22 June 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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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (55)Excellent
    0.3 kilometres 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 10 July 2018
    This is either the second or third time we've stayed here so that should tell you its quality. Beautiful condo with everything you need for a comfortable home away from home...
    Reviewed 26 May 2018
    Joanne and Jim were very nice and helpful! I loved the house and the location is superb! Beautifully furnished and comfortable. My only concern was the lack of hot water in...
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.3 kilometres from Harry S. Truman Little White House
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 and full size oven. Ample storage space in kitchen to...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    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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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    The Banyan Resort at Key West1 / 6
    (1)Excellent
    0.2 kilometres 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 Garden
    • 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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    A Place In Paradise1 / 24
    (23)Very good
    0.3 kilometres 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)
    • Wi-Fi
    • Balcony
    • Parking
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 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 13 November 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
    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 spend your vacation in a quiet gated community surrounded by historic buildings and...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Harry S. Truman Little White House
    4 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 10
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    Key West home w/shared pool and just steps from historic Old Town1 / 24
    (1)Excellent
    0.3 kilometres 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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    0.4 kilometres from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    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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    0.4 kilometres 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
    • Cable/satellite TV
    • Private Garden
    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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    The Water's Edge1 / 25
    (2)Excellent
    0.3 kilometres 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 7 March 2017
    The house was gorgeous, and the sunset view from the balcony lived up to expectations... Short walk to Duval Street... Totally recommended
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    About this property
    Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Breezy Bungalow1 / 24
    (1)Excellent
    0.3 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Terrace
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    Great location - within walking distance of Duval Street, Mallory Square, Hemmingway House, and many other attractions that we visited. The Truman complex, where it is located...
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    Breezy Bungalow - Weekly Rental When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside breezes to flow openly into Breezy Bungalow. Two levels of...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.3 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Terrace
    • Parking
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CAPTAINS WHEEL: Take control of your vacation, be the master of your fate. Captains Wheel will not disappoint. Situated on the corner of Southard and Emma Streets in Truman Annex, a most prestigious gated community in the heart of historic Old Town. 2 bedrooms, 2.5 baths; each queen-bed room has...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sundown Refuge1 / 23
    (9)Excellent
    0.0 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
    • Parking
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 November 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 2 March 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
    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 spend most of your time overlooking Florida Bay in one direction and Truman's Little White House in the other...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    A Touch of Bermuda in Key West1 / 19
    (17)Excellent
    0.4 kilometres from Harry S. Truman Little White House
    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 10 October 2017
    By the time you arrive, you will already feel like you are part of Jack's family. He will literally bend over backward to accommodate you. We have vacationed in Key West for...
    Reviewed 15 July 2017
    I stayed in Jack's condo (a touch of Cuba in Key West) this past week and we enjoyed every aspect of it. The condo is two bedroom one bath and was perfect for my party of three...
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    About this property
    Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is just past the...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bahama House1 / 24
    (27)Very good
    0.5 kilometres from Harry S. Truman Little White House
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 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 13 April 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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    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 around the corner from the fabulous shops, activities, restaurants and nightlife on Duval Street. Luxuriously appointed...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Royal Palm1 / 25
    (4)Very good
    0.0 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 February 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 14 September 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
    DISCOUNTED RATES for Open Dates this SUMMER! 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...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Alluring Porches1 / 24
    (17)Very good
    0.3 kilometres from Harry S. Truman Little White House
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2018
    Everyone in our group loved the place. It was clean and well stocked with about anything you need. A porch off both bedrooms and a small, secluded deck that was perfect. It's...
    Reviewed 1 November 2015
    Everything as advertised and more. Immaculate, tastefully decorated, roomy. Close to Duval. Porches on each bedroom and off living room. Huge master bedroom with large porch...
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    About this property
    ALLURING PORCHES - A beautiful 2 bedroom 3 bath townhome with an additional den, is the tranquil escape you have been looking for. Wonderfully decorated with Key West charm and unique art work, stunning orchids surround this home and a beautiful open air feel brings the outside in while you just...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.2 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This amazing penthouse condo has one of the best view in Key West. Located in historic Mills Place in the main part of Truman Annex, you have the views of the Gulf and ships that pass by the windows as they arrive and leave port. The apartment has four exposures and three of them with balconies....
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Casa Havana1 / 24
    (3)Average
    0.4 kilometres 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 Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 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 23 February 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Shipyard Treasure1 / 26
    (53)Excellent
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Terrace
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    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 18 February 2015
    Shipyard Treasure is welcoming, comfortable, condo, decorated with Key West art in the bedrooms, living room, and entry, and with wonderful beds, bedding, and much better than...
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    About this property
    SHIPYARD TREASURE: Contemporary Condo at Truman Annex - Walk to Beach/Duval Street Decorated in casual contemporary style, this second floor Shipyard condo is centrally located in the Truman Annex, within quick walking distance to all the sites and attractions of Old Town Key West. Relax in 2...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Bloom'n Paradise1 / 24
    (3)Excellent
    0.0 kilometres from Harry S. Truman Little White House
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2017
    The photos do not impart the beauty of this property. It is perfectly appointed and convenient to Mallory Square and all of Old Town Key West. Jeff is a wonderful host and the...
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    About this property
    BLOOM'N PARADISE - Relax in luxury in this beautiful Truman Annex private vacation home for rent in the Florida Keys. This property features three bedrooms and three bathrooms in the main house plus a pool house with one bedroom one bath. On Admiral’s Lane in the Truman Annex community, this...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Foundry on the Waterfront ~ Weekly Rental1 / 10
    (2)Very good
    0.0 kilometres 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 15 May 2014
    The condo was very comfortable and in a great location in being able to walk about anywhere. The only item from the 5th star is the matteresses could be replaced.
    Reviewed 29 November 2011
    This unit was in the perfect location to experience Duval Street and Mallory Square. Close walking distance to everything and yet just far enough away so you do not hear the...
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    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Linger Longer1 / 23
    (22)Very good
    0.3 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2015
    I am a repeat renter and plan to return next year. Walking distance to everything but in a quiet community off Duval.
    Reviewed 27 April 2014
    This was the first trip to Key West for my husband and I, but we traveled with more experienced Key West-ers who booked the rental. We were pleasantly surprised when we arrived...
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    About this property
    LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath home rental Florida Keys, located in the President's Walk of Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either side of the full bathroom on...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Banana Key1 / 25
    (7)Excellent
    0.0 kilometres 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 yesterday
    Really nice space. I would rent again. Great location. Clean, you can easily have 4 people in this property.
    Reviewed 3 weeks ago
    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
    DISCOUNTED RATES for Open Dates this SUMMER! 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...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Easy Livin'1 / 24
    (1)Excellent
    0.0 kilometres from Harry S. Truman Little White House
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Balcony
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.0 kilometres from Harry S. Truman Little White House
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.1 kilometres from Harry S. Truman Little White House
    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
    About this property
    DISCOUNTED RATES for Open Dates this SUMMER! 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...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    The Courtyard1 / 25
    (21)Very good
    0.6 kilometres 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 17 April 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 18 August 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
    DISCOUNTED RATES for Open Dates this SUMMER! 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...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.1 kilometres 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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    0.3 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SOUTHARD GETAWAY: Imagine it. Arrive in Key West to a beach-like home in walking distance to all that Key West has to offer. Yes, that's Southard Getaway. Two queen bedrooms upstairs with full bath, open living space downstairs with quiet, shaded deck. Decorated in hues of blue and green that...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    0.0 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Balcony
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Townhome, 2 Bedrooms, 2.5 Baths, (Sleeps 4) Available for weekly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful gated Truman Annex community. It’s close to all the major attractions yet just far enough away to be quiet and relaxing. Duval Street,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.2 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please note: this property is only available for Dec23 to 30, 2018. Discover this relaxing Key West resort oasis in the heart of Key West's famed Old Town, right at Mallory Square! At Hyatt Residence Club Key West, Sunset Harbor, we're one of the best resorts in Key West. Toast another perfect...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 kilometres 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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Harbor Walk Hideaways1 / 22
    (20)Excellent
    0.6 kilometres from Harry S. Truman Little White House
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
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    Amenities & Details
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 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 26 October 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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    Admiral's Lane1 / 20
    (23)Very good
    0.1 kilometres from Harry S. Truman Little White House
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 April 2018
    Nice house in a great location. 2 blocks from Duval Street, but quiet at night. Adequate pots and pans for cooking in. Nice bedrooms and bathrooms. Front porch and living room...
    Reviewed 13 June 2017
    We booked a family trip to Key West to celebrate a few wedding anniversaries. Since there was 8 of us, we opted to rent a condo and we were NOT disappointed! This place on...
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    About this property
    DISCOUNTED RATES for Open Dates this SUMMER! As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Havana Hideaway1 / 25
    (21)Excellent
    0.0 kilometres 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 yesterday
    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 18 April 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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    Key West Casa1 / 24
    (26)Very good
    0.4 kilometres from Harry S. Truman Little White House
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2017
    We just recently returned from our stay in Key West Casa. This condo has everything you need. We did not use the bikes because we did not know how to unlock them, but we never...
    Reviewed 12 June 2016
    We stayed in Key West Casa and absolutely loved that property. It is a 3 bedroom, 2 bath with a porch, back patio, balcony. The kitchen is fully equipped, one of the best we've...
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    About this property
    KEY WEST CASA – Beautiful and spacious Shipyard condo Key West, Key West Casa is one of only a few 3 bedroom 2 bath condos in the Shipyard complex. This great rental property is located in the prestigous Truman Annex community just 2 blocks to famous Duval Street and walking distance to shopping,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    President's Walk1 / 24
    (1)Excellent
    0.3 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    This place was perfect for the three adults and infant. The proximity to the pool, Duval St., and Green Parrot really made this beautiful condo ideal for a long Key West trip...
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    About this property
    PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same location; now it's your turn. President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind. Situated directly in front of one of the community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.4 kilometres from Harry S. Truman Little White House
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated on the second floor of a historic home, this spacious dog-friendly condo welcomes guests with great amenities and a private hot tub! Soak after a long day in the sunshine, and fire up the gas grill to make full use of the back patio space. You're right around the corner from Duval...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    0.4 kilometres from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Terrace
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West is like a little piece of the Caribbean at the lowermost point of the United States: it’s reliably warm, the waters are a gorgeous turquoise, and it is a small, intimate community. From this second floor condo it’s just a short walk to Mallory Square’s sunset celebrations, the Ernest...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Siesta Bay1 / 25
    (3)Very good
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 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 19 March 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
    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 want to do in Key West. Bright, airy and with plenty of Key West charm, Siesta Bay will provide you with all the comforts...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Truman Annex Irish Condo Innisfree1 / 33
    (5)Excellent
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2016
    This was my 2nd time staying in the Shipyard section of the Truman Annex. Each time was in a different 2BR condo. this condo was clean, well equipped with kitchen, bath...
    Reviewed 25 January 2016
    I attended college at a later age and upon graduation took 2 friends and my sister to Truman Annex for a 10 day vacation!!! We had the best time. As a matter of fact I am back...
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    About this property
    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Dolphin House1 / 23
    (3)Very good
    0.2 kilometres from Harry S. Truman Little White House
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Grill
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 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
    THE DOLPHIN HOUSE: Twice the comfort and twice the amenities - located in the exclusive Truman Annex. The Dolphin House Key West Vacation Rental is comprised of a bright and open main house and a lovely and bright guesthouse, with a pool and outdoor living space comfortably nestled in between....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Emma's Escape1 / 23
    (4)Excellent
    0.6 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2013
    We have been staying at 717a Emma for four years now. We started for one month and next year, we'll be there for three. I think that this property has one of the most amazing...
    Reviewed 6 February 2013
    Once again we enjoyed our winter stay in Key West. The climate in the main attraction, but Key Westalso full of interesting people and places. The condo became a home away...
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    About this property
    Emma’s Escape (monthly rental): Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life. A fabulous location that will allow you to walk or bike to all the island highlights. In the heart of Old Town,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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