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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 March dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    1/2 Block to Duval, World of its own -Nassau Suite1 / 17
    (42)Excellent
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Steps to Duval, Old Town Charm -Grand Bahama Suite1 / 11
    (72)Very good
    0.4 kilometres from Harry S. Truman Little White House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Best Location, 1/2 Block to Duval, Bimini Suite1 / 17
    (53)Very good
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Center of It All - Paradise Island Suite1 / 14
    (39)Excellent
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2019
    We had a girls weekend in the paradise suite. Upon arrival, the code we setup a couple of days before was not working. Called customer service and the lady was being extremely...
    Reviewed 30 May 2019
    Awesome location, close to everything ya need n can walk to house is great clean , very nice I’d definitely stay here again when I come back down . I’m very happy our group...
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    About this property
    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Ocean Views
    • Terrace
    • Washer
    • Central Heating
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2 bedroom, fully furnished condominium is located in the Truman Annex, a gated community of private homes and condominiums. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture, queen bed with two twin...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    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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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Walk or Bike!! Truman Annex: 3 BIKES, 2 PORCHES, A POOL, WIFI, & PARKING1 / 41
    (15)Excellent
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Balcony
    • Waterfront
    • Washer
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2019
    The owners, Ed & Kerry are tremendous people to work with. I will definitely book their condo again. They are a 5 star operation. Thank you for a wonderful experience.
    Reviewed 22 June 2019
    We had a wonderful week, fully immersing ourselves in the Key West culture! The condo was perfect for our stay, as we walked or biked everywhere. Thank you!!!
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    About this property
    Billy's Blue Heaven is fresh, clean and Pristine. Our condo includes one parking spot for an automobile directly in front of our condo. We're just a two minute walk to Duval Street and only 300 steps to the world famous Ricky's Blue Heaven Restaurant. The balcony overlooks Truman Annex 's lush...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.0 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Balcony
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Townhome, 2 Bedrooms, 2.5 Baths, (Sleeps 4) Available for weekly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful gated Truman Annex community. It’s close to all the major attractions yet just far enough away to be quiet and relaxing. Duval Street,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Key West home w/shared pool and just steps from historic Old Town1 / 29
    (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
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bright Key West Beauty 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....
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    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    *** Fantastic Fall Prices- Last minute discounts- Stay Downtown & Save ***1 / 36
    (5)Excellent
    0.4 kilometres 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 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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    Historic house w/ private pool & easy beach access - ideal for groups! Dogs OK!1 / 31
    (1)Very good
    0.4 kilometres from Harry S. Truman Little White House
    7 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
    • Patio
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 May 2016
    We stayed in one of the units at the property (Banana Split). This is a 1 bedroom / 1 bath apartment on the second floor. It has a full kitchen, small sitting area and two decks...
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    About this property
    Banana's Foster Guesthouse Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large historic house on Key West. Featuring a private heated pool, four private parking spaces, and a communal area with plenty of room for everyone, this seven-bedroom,...
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    Stock Island, Florida Keys
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 18
    0.0 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • DVD Player
    • Terrace
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Ocean Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunset at Harbour Place Enjoy this spectacular condo with an oceanfront view of Key West harbor for your next getaway in the Key West! Located in Truman Annex, this home boasts beautiful water views from the balcony and all around the condo, you'll be sure to feel inspired during your stay! This...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.2 kilometres from Harry S. Truman Little White House
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Balcony
    • Washer
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Last Minute Enjoy the unbeatable location of this two-story home only a block away from Duval Street. Take advantage of the large open concept living room, kitchen, and dining spaces while relaxing indoors. You can also beat the Florida heat by cooling off in the pool. This home is ready-made for...
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    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.0 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bliss This cozy Key West rental is ready to be your home away from home! Located on a tree-lined street in the Truman Annex community, this townhouse offers a full kitchen, patio, and a shared pool. Just a half-mile away, experience the excitement of Duval Street for shopping, dining, and...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Dog-friendly condo w/ shared pool, full kitchen & parking - central location!1 / 27
    (2)Very good
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    The location was fantastic. We were there with a large group and rented out the entire house (including this 2BR/2.5BA main house plus all of the other 1BR guest suites). All of...
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    About this property
    Sweet Caroline The tranquil majesty of Key West will be at your fingertips when you stay at this homey two-bedroom, two-and-a-half-bathroom condo, with a shared pool and a great location near the beach! Part of Banana's Foster Guest House in the center of downtown, you'll be within easy walking...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Salty Air Retreat Find tropical ease and comfort at this two-bedroom Key West condo, where you'll enjoy a private garden patio, a community pool and terrace, and a perfectly walkable location in one of the most desirable downtown neighborhoods. You'll find this condo in the Truman Annex...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.1 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Washer
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mangrove Lagoon Find the utmost in beauty and convenience at this two-bedroom Key West home, a light-filled escape with a private patio, a heated community pool, and an ideal location close to beaches, nightlife, restaurants, and historic sites. You'll find this elegant home in the Truman Annex...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Cozy studio condo w/ shared pool & courtyard - easy beach access! Dogs OK!1 / 27
    (2)Very good
    0.4 kilometres from Harry S. Truman Little White House
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2016
    Loved the stay here. Close to Duvall. Could walk to anywhere on the island including historical sites, any restaurant. Centrally located. Rooms very clean and spacious. Only...
    Reviewed 11 November 2014
    This place was perfect for what we were looking for:Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
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    About this property
    Key Lime Cottage Let time wash over you in gentle waves while you relax in the sunny paradise of Key West at this cozy studio condo, offering access to a shared pool, courtyard, and an easy walk to the soft sandy beach. Located in the heart of downtown Key West as part of the larger Banana...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Pelican *Please note that this home requires minimum stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. You'll be mere steps from dining, shopping, nightlife, and a wide variety of attractions at this darling Key West home, perfectly situated on...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    0.4 kilometres from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Banana Split Shed your stress and dive into the sublimity at this homey one-bedroom condo in Key West. Featuring access to a shared soaking pool, a full kitchen, and private off-street parking, this is the perfect home base for all your ventures in paradise! Part of the Banana's Foster Guest...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 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
    0.4 kilometres from Harry S. Truman Little White House
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Creme Brulee Getaway Bask in the glorious waves and sunshine of Key West at this second-floor studio, featuring a shared pool, one private parking spot, and close proximity to the beach, restaurants, and more! This studio is part of Banana's Foster Guest House, which can accommodate a much larger...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Studio condo w/ shared courtyard & pool - walk to everything - dogs welcome!1 / 29
    (1)Very good
    0.4 kilometres from Harry S. Truman Little White House
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2016
    If you're looking for an affordable place to crash at the end of a few crazy Key West days and nights, this is perfect. Terrific location, right at the intersection of Simonton...
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    About this property
    Sugar Pie Suite Bask in tropical sunshine and waves in the paradise of Key West for your next vacation with this cozy studio. Featuring a kitchenette, shared pool, and courtyard in an awesome central location, two guests will feel right at home here. The family dog is also welcome here for an...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Sunny tropical condo with a shared pool, close to all of the beachside action1 / 26
    (5)Very good
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 November 2012
    Arrived with spouse and our 2 adult children. This condo was clean, had all the amenities that we could have hoped for. Nice quiet neighborhood, yet close to Duval St...
    Reviewed 7 February 2011
    Close to Duval St, and Mallory Square - within a 10 min walk with small kids. Amenities were great - kitchen, washer/dryer, family room. Access to pool. Looking forward to a...
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    About this property
    Seashore at the Shipyard Boasting a great location in the Truman Annex, a shared pool, and easy beach access, you won't have to go far to dive into the beachside fun! Less than a mile to the picturesque Mallory Square and just under a mile to Fort Zachary Taylor Historic Park, there will be no...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.4 kilometres from Harry S. Truman Little White House
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Honey Bun Hideaway Pack your bags and leave your worries behind for an exciting trip to Key West! This studio has everything you need to have a great time, including access to a shared pool, an outdoor dining area, and nearby beach access for endless sunny days. Part of the larger Banana's...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (80)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 3 weeks ago
    Cassa Del Sol is a wonderful condo. It met and exceeded all our expectations. Thank you for a great stay in your lovely, well equipped condo. We will stay there again!Brenda...
    Reviewed 4 weeks ago
    This is the second time we enjoyed Jim and Joanne's home. I love that it has 2 en suite bedrooms so both couples feel like they have a master bedroom. The location is perfect in...
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    President's Walk1 / 26
    (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
    • 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
    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
    0.3 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • 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
    Bayview Harbor1 / 24
    (1)Average
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • DVD Player
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2019
    This unit was nice and well maintained. We enjoyed sitting out on the front porch in the morning greeting people walking or bike riding by. FYI there is no oven. Sometimes...
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    About this property
    Looking for a peaceful retreat yet close to everything? Ideally located on Southard Street, within walking distance to the beach at Fort Zachary Taylor State Park, Duval Street and Mallory Square, Bayview Harbor is the spot you’ve been looking for. This unique property is newly renovated to...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Artist Garden1 / 24
    (27)Very good
    0.1 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 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 11 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 events. Artist Garden makes an ideal vacation rental for those who like to enjoy Duval crawl and quiet peaceful vacation at the same time A bright and breezy 2 bedroom 2.5...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.4 kilometres from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    The Water's Edge1 / 27
    (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
    • Patio
    • Ocean Views
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • 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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Key West Found1 / 24
    (32)Very good
    0.0 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Balcony
    • Parking
    • Wi-Fi
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 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
    0.2 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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
    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
    other travellers have booked this property
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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
    The Mermaid's Garden1 / 24
    (1)Excellent
    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
    Reviewed 13 September 2018
    The Mermaid Garden is close to all of Key West's attractions yet nestled in a quiet historical location. The house has plenty of room, the kitchen has everything you might need...
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    About this property
    Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized brass mermaid sculpture installed in a garden bursting with tropical ferns and palms. A few...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    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
    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 just blocks away, is Old Town's premiere...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Island Style1 / 25
    (1)Excellent
    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
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2019
    Nice place. Comfy home. Location is perfect for Key West. Pool is a small square. Beds are comfortable. Kitchen is stocked with what you need. Good find. Would stay again.
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    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
    The Green House -Cool Shade1 / 7
    (1)Excellent
    0.4 kilometres 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 24 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
    Finn Key1 / 24
    (33)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
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2018
    I traveled with my best friend and her husband to Key West, and we decided on renting Finn Key for about a week. The location was phenomenal - we barely needed the car! We could...
    Reviewed 11 February 2016
    Lovely condo,great location, have stayed at Truman many times. Condo is clean and comfortable, neighbors upstairs must live here full time, they walk a little heavy but I...
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    About this property
    Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat! A beautiful 2 bedroom 1 bath downstairs condo located in The Shipyard section of Truman Annex. This pristine residential community is one of the most requested locations in the heart of Old...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    City Cay1 / 22
    (4)Very good
    0.4 kilometres from Harry S. Truman Little White House
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2017
    We stayed for a week at City Cay. The location could not have been any better. The condo was supper clean and well maintained. We would definitely stay here again! It is a one...
    Reviewed 2 August 2016
    We loved City Cay. It was a small condo with one king bed, a futon and a small kitchen, but it was exactly what we needed. The bed was super comfortable. The bathroom was...
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    About this property
    Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This understated Truman Annex Condo is the place! City Cay is our 1-bedroom 1-bath upper level condo that has been meticulously renovated and furnished in a sleek modern style of the hippest urban...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    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 4
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • 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! 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
    0.4 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check-in Check-out
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    Payment Protection
    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
    Crowner's Jewel1 / 24
    (35)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
    • 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
    Heavenly Hideout at Rainbow's End ~ Weekly Rental1 / 33
    (9)Very good
    0.3 kilometres from Harry S. Truman Little White House
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Balcony
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2018
    The accommodations were very nice. Mattresses in every room could definitely use some updating, everyone in our party agreed all the beds were hard and you could feel the...
    Reviewed 23 October 2017
    We (8 adults) stayed at Heavenly Hideout at Rainbow's End in Oct 2017. Due to hurricane Irma we were concerned for the residents of the Keys as well as the property and honestly...
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    About this property
    Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time. But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This tropically...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    0.3 kilometres from Harry S. Truman Little White House
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ​Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private President's Lane area of the prestigious Truman Annex. Offering exquisite amenities, pool access, and an unbeatable location close to Duval Street, Truman Waterfront Park, and Ft. Zachary Taylor...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Linger Longer1 / 26
    (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
    • 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
    A Barefoot Retreat1 / 27
    (1)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
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for the perfect home away from home? No need to look any further! No shoes needed at “A Barefoot Retreat” in the lovely Shipyard section of the historic Truman Annex private community. This two-bedroom, one bath, upper floor condo will feel like your own tropical home the minute you...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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