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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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    All 145 Rentals in Key West
    Shipyard-1/2 Block Duval Street1 / 9
    (1)Excellent
    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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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    0.0 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    ** Fantastic Spring& Summer  Stay Downtown walk everywhere **1 / 36
    (5)Excellent
    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2016
    This was my 2nd time staying in the Shipyard section of the Truman Annex. Each time was in a different 2BR condo. this condo was clean, well equipped with kitchen, bath...
    Reviewed 24 January 2016
    I attended college at a later age and upon graduation took 2 friends and my sister to Truman Annex for a 10 day vacation!!! We had the best time. As a matter of fact I am back...
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    About this property
    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location1 / 28
    (3)Excellent
    0.3 miles from Harry S. Truman Little White House
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
    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 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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Conch Haven Old Town 1/1 MONTHLY Rental1 / 16
    (5)Very good
    0.6 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Porch
    • Balcony
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 2020
    We have been spending at least a month in Key West every winter for 6 years, usually on our boat. This year we rented this property and really enjoyed it. It is furnished with...
    Reviewed 23 September 2019
    Two months is not enough for me, would like to live there.This is my second year I stay at this house with family visiting couple of times.The owners Stephanie an Donna are...
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    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (83)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
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    • Internet Access
    • Cable/satellite TV
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2020
    We stayed at Casa Del Sol over New Year's Eve as a family of 4. The townhouse was just as advertised, well appointed in a wonderful location. The weather was beautiful and we...
    Reviewed 28 December 2019
    The location is fantastic. It is walking distance from so many restaurants, places to see and of course Duvall St. which is only 2-3 blocks away. The condo is beautiful. From...
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    0.6 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Parking
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking. Here your vacation dreams come true. Centrally located on one of Old Town's most popular streets, nestled in a tranquil corner of a sought-after gated compound with lushly landscaped walkways leading...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    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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    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Porch
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2017
    We have stayed here 2 or 3 times. It is small, but there are just 2 of us and our dog. Works for us! Very cute and cozy. Washer & dryer. Compound is quiet and...
    Reviewed 13 August 2016
    The Cigar House has one the best location you can expect in Key West, close to Fort Zachary, Hemingway's House or Duval St. and all its attractions.This lovely house is full of...
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    About this property
    OVERVIEW The Cigar House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of four (4) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (1) queen...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    President's Walk1 / 26
    (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 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
    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 pools in the...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    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 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
    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
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree. Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer. Located in the exclusive gated community of the Truman Annex, this...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    HISTORIC KEY WEST  - Conch House - Sleeps 51 / 21
    (6)Very good
    0.4 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Porch
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2019
    A perfect stay for myself, my husband and 12 year old son; we wished we could have stayed longer and would love to return! A meticulously clean and hip home with an airy...
    Reviewed 27 June 2019
    Pros: Cute cottage in a great central location to Duval, Hemingway house, fort Zachary. Adequate dishes and pans to cook with though could use pizza cutter. Owner included...
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    About this property
    OVERVIEW The Conch House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open sociable living environment - (2) queen beds, and (1)...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    0.6 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfect spot offers plenty of private outdoor space within walking distance of great restaurants and shops. Located in Old Town in a small, quiet compound of cottages sits William's Loft in one of Key West's most desirable neighborhoods. A secluded community surrounded by lush tropical...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    Artist Garden1 / 24
    (27)Very good
    0.0 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2015
    We stayed at the Artist Garden for our triple birthday celebration (3 friends within a week). The house is beautiful. It is located within Truman Annex. And you can seriously...
    Reviewed 10 April 2014
    We enjoyed a 2 week stay in this beautiful house. The location is perfect. We were only a 5 minute walk to Mallory Square and a 10-15 min walk to other favorite restaurants. We...
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    About this property
    This spacious home with a large outside deck is tucked away on a quiet lane of Truman Annex, yet only a short walk to all attractions. Artist Garden makes an ideal vacation rental for those who like to enjoy a Duval crawl and a quiet peaceful vacation at the same time A bright and breezy 2...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    The Mermaids House, Historic Old Town Key West1 / 38
    (36)Excellent
    0.4 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2016
    The Mermaid's House has an ideal location, half a block off Duval St and almost directly in the middle of both coasts so easy access to view sunrises and sunsets. The short walk...
    Reviewed 18 December 2015
    Let me start by saying I don't think I've ever stayed at a vacation rental so thoughtfully set up with everything a guest could possibly need. Kudos to Barbara! I loved the...
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    About this property
    Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    ** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **1 / 27
    (13)Very good
    0.6 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Balcony
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2015
    My (adult) daughter and I drove down to Key West for 4 days/nights - I had only been there once; she had never been there. We are from the midwest - it was hard to choose a...
    Reviewed 18 August 2014
    This small townhouse was absolutely the most convenient thing we could have asked for in Key West. 1/2 block off Duval Street at Truman. We literally parked the car and walked...
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    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Key West Found1 / 24
    (32)Very good
    0.0 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Balcony
    • Parking
    • Wi-Fi
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2018
    This was a great vacation rental! My daughter got married in Key West and Key West Found was the perfect home for us to be close to venues, and of course all that Key West has...
    Reviewed 5 April 2015
    The Foundry in Truman annex is where I stay every time I vacation in KW- close to everything but quiet & peaceful for relaxation.
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    About this property
    Just steps away from Harry Truman's 'Little White House' you’ll find your vacation dreams come true! Located in the historic brick Foundry building, Key West Found is a spacious two bedroom, two and a half bath, three-story townhome. Enter through a wrought iron gate to your own tropical...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.1 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Balcony
    • Internet Access
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautifully appointed Gulf front Condo in the heart of Truman Annex. Mills place features a walkway flanked by Royal Palms. Mills place was the old military Hospital building. In the mid 80's it was purchased by a developer who renovated the entire property in keeping with the existing...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.5 miles from Harry S. Truman Little White House
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Terrace
    • Balcony
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home. This tropically inspired three level property has all the updated amenities for you and your guests to enjoy, plus be within walking distance of the Southernmost Point, the Hemingway...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    0.6 miles from Harry S. Truman Little White House
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Duval Breeze1 / 24
    (57)Very good
    0.6 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 February 2020
    Location is great, very convenient. Unit was super clean. Rented for two weeks. On day six parking pass was lost,called AT HOME AT KEY WEST. At this time I was asked if they...
    Reviewed 6 July 2015
    First off At Home in Key West is awesome. We have used them twice and never had any trouble at all. They are very prompt, courteous and a delight to deal with. The condo...
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    About this property
    Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches! Enjoy the great location of this beautiful 2 bedroom 2.5 bath vacation home key west located in the gated rooftop community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    • Shared Outdoor Pool (Unheated)
    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
    Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street. 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...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Bright Shipyard Condo1 / 10
    (1)Excellent
    0.3 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Balcony
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2020
    What a great condo in paradise. The condo is very clean, comfortable, well appointed, inside a gated community with the pool very close. The location was perfect within...
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    About this property
    Located in Shipyard Condos Truman Annex and is available for weekly or monthly rental. The ideal location of this super-comfortable, 2nd floor, corner property makes it the perfect blend of convenience, tranquility, and tropical Key West scenery. Sit back and relax as you sip cocktails on the...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.6 miles from Harry S. Truman Little White House
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    HISTORIC KEY WEST - Turtle House - Sleeps 61 / 24
    (3)Very good
    0.4 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Porch
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 November 2018
    The Turtle House is a very nice house to rent, conveniently located on Thomas Street, which is close to the wide variety of stores and restaurants on Duvall Street in downtown...
    Reviewed 22 June 2017
    Spacious property with two pools, friendly neighbors and charming location just a short walk to all of old town Key West.
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    About this property
    OVERVIEW The Turtle House is a 100+ year old recently completely renovated historic house. The house can comfortably accommodate a maximum of six (6) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas. The house can be described...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Sunrise off Southard- A Tropical Sanctuary Newly Remodeled in May1 / 38
    (1)Excellent
    0.2 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    • Secure Parking
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, Location, Location!! Sunrise off Southard has it all! An upscale one bedroom home offers tropical beauty with all the comforts. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    0.2 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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
    Key West Suites Hotel 2051 / 16
    (2)Very good
    0.3 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 March 2020
    We did not sleep well in this unit. Was right next to a bar with super loud music. We complained to police and it got better for that night, but still bad. Every single night...
    Reviewed 21 March 2019
    I never normally write reviews for places, but this place was great! I stayed there for a few days with my friends and had never been to Key West before and this place had...
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    About this property
    Key West Suites Hotel 205 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Key West Suites Hotel unit 2011 / 16
    (1)Excellent
    0.3 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2019
    Stayed at this apartment for New Year’s Eve, location is exceptional! Owners were available at all times for questions/concerns. The unit was very clean and equipped. It was...
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    About this property
    Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both Duval and Southard Streets....
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Brand New! Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.1 / 42
    (1)Excellent
    0.5 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 December 2018
    We stayed here November 2018 for our 25th wedding anniversary and loved this place.Totally charming, faithfully restored cottage with all the modern amenities. We found...
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    About this property
    Experience what is like to live in Old Town at the desirable Historic Seaport. This beautiful home is filled with amazing furniture, artwork and amenities that give you the tropical, old town feel you seek when visiting Key West. The smallest details have not been missed, high thread count...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Octopus's Garden Off Duval1 / 26
    (1)Excellent
    0.4 miles from Harry S. Truman Little White House
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2019
    Stayed here with 6 other people last month. The location is perfect - half block off Duval - but on a private lane. Everything is brand new. High end finishes. Luxurious...
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    About this property
    Perfectly located and fully remodeled in 2018, Octopus's Garden is steps from Duval Street and the home of Ernest Hemmingway. The homes historical outer appeal gives way to a modern designed interior that is furnished to perfection! This stunning 3 bedroom / 3 bathroom features a formal...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.1 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, Beauty and Comfort! Kokomo Korner has what you are looking for! This upscale home has been meticulously designed with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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
    • DVD Player
    • Terrace
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 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 5 November 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! Experience the finest in vacation home rentals in Key West Florida when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in the heart...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.5 miles from Harry S. Truman Little White House
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West. For anyone with an affinity for the sea, everywhere you turn is a reminder of the water – from sailboat replicas of every shape and size; prints of fish and sailor...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    The Green House -Cool Shade1 / 7
    (1)Excellent
    0.2 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2019
    The condo was simple and cute Very clean and had all of the things we needed. Owners were available but not evident if we needed anything and always got back to us quickly...
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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
    Linger Longer1 / 26
    (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
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Terrace
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Parking
    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
    Just imagine stepping out of the rental and stepping right into the pool! Just relax and enjoy your vacation! 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...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    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
    Ibis1 / 24
    (2)Very good
    0.6 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 March 2011
    My location was so convenient that I could walk everywhere and I did. I loved the fact that it was so quiet at night. When I needed service on the microwave, it was provided...
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    About this property
    Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home. There is a potential deck work scheduled for sometime in August and part of September which will not affect pool usage...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.4 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This idea has been several years in the making and has been finally able to come to fruition this summer. Taking the best parts of boat life and combining them with the space and comforts of home, this Tiki Suite has been designed to be the ultimate glamping experience on the water. Outside, in...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.2 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming condo with large front porch & fantastic location. Great for couples on a weekend getaway or a small group of friends looking to be in the heart of Old Town Key West. Fresh, modern space, and full amenities make Mary's Backyard an excellent choice. You are never far from the water here:...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.5 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table. Check out the history and architecture of Old Town. All these options and many more are yours...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    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
    • Shared Outdoor Pool (Unheated)
    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
    Located on Porter Lane of Truman Annex you can find your real 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...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you're lounging on the front porch's rocking chair or enjoying a seafood dinner inside, Mary's Backyard Too is your home base for Key West adventures and relaxation. This home's great location and relaxed atmosphere invite you to embrace the island lifestyle. This home is located in the...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Tranquility1 / 24
    (31)Very good
    0.6 miles from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    Tranquility is a true Key West experience...clean cottage, clean pool, great location! Plan to rent bikes as parking is VERY limited and once you park your car you will not...
    Reviewed 28 June 2015
    The Tranquility Cottage (#5 at The Colony Cottages) is adorable. The cottage is bright, cutely decorated, and the compound is quite inviting. It is conveniently located and an...
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    About this property
    Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Key Lime Pie1 / 22
    (7)Average
    0.6 miles from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 December 2012
    Our stay was for a month and the property was great and the location was awesome We walked to everything we need and was on a nice quite street(lane) Great neighbors
    Reviewed 26 April 2012
    We returned here to stay for 6 weeks and we like the location. Thankfully, the bed mattress has been replaced and there have been a few other updates and new wifi which we...
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    About this property
    Key Lime Pie is the private cottage that perfectly encompasses the “Key West vibe” that you’re looking for. The minute you walk in to see the bright, sunny walls and local artwork, you know you are somewhere special. This rental has all the amenities required for a memorable stay – including a...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Collins offers a central location to Key West’s main attractions and everything else the Southernmost city has to offer. With a balcony overlooking Duval Street you can be as much connected...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    0.2 miles from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This unique property offers a central location to Key West’s main attractions and everything else the Southernmost city has to offer. With a balcony overlooking Duval Street you can be as much...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Sundown Refuge1 / 23
    (10)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
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2018
    We are soon on our way down for our twice a year trip to Key West and we always stay at Sundown Refuge if it is available. It is in easy walking distance of all the the...
    Reviewed 26 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...
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    About this property
    View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building! Balmy breezes, brilliant sunrises, and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex. You'll spend most of your time overlooking...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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