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Holiday Rentals nearby Mallory Square

400 Wall St, Key West, Florida 33040-6633
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    ₹ 25,361 Average
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    All 100 Rentals in Key West
    0.4 kilometres from Mallory Square
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West home w/shared pool and just steps from historic Old Town1 / 29
    (1)Excellent
    0.7 kilometres from Mallory Square
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (83)Excellent
    0.7 kilometres from Mallory Square
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    ** Fantastic Spring& Summer  Stay Downtown walk everywhere **1 / 36
    (5)Excellent
    0.8 kilometres from Mallory Square
    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
    Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (4)Excellent
    0.9 kilometres from Mallory Square
    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
    6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location1 / 28
    (3)Excellent
    0.7 kilometres from Mallory Square
    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
    Casa Havana1 / 24
    (3)Average
    0.2 kilometres from Mallory Square
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2018
    Location is the best. Casa Havana is 1/2 block off of Duval and 3 blocks from everything in Key West. Deck is great for drink and a cigar in the afternoon and having it own...
    Reviewed 23 February 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group...
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    President's Walk1 / 26
    (1)Excellent
    0.7 kilometres from Mallory Square
    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
    0.7 kilometres from Mallory Square
    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
    Artist Garden1 / 24
    (27)Very good
    0.4 kilometres from Mallory Square
    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 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
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    Key West Found1 / 24
    (32)Very good
    0.4 kilometres from Mallory Square
    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
    0.4 kilometres from Mallory Square
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • Air Conditioning
    • Patio
    • Private Garden
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commodore's Compound Spend your Key West vacation in style here at this high-end house! There's plenty of room for everybody in this house's eight bedrooms, and you're steps away from the ocean. Key West's most popular attractions surround this home - walk down to Mallory Square a few blocks...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
    Crowner's Jewel1 / 24
    (35)Very good
    0.6 kilometres from Mallory Square
    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
    Linger Longer1 / 26
    (22)Very good
    0.7 kilometres from Mallory Square
    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
    Historic house w/ private pool & easy beach access - ideal for groups! Dogs OK!1 / 31
    (1)Very good
    0.4 kilometres from Mallory Square
    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 26 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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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 18
    0.8 kilometres from Mallory Square
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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
    0.7 kilometres from Mallory Square
    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
    Contemporary beachside escape with shared pool and close to local attractions1 / 25
    (4)Very good
    0.9 kilometres from Mallory Square
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2014
    We had a wonderful time staying in Key West. The condo location was perfect. We walked everywhere. The beds were comfortable, and although the kitchen is very small, it was...
    Reviewed 12 March 2014
    This place is a very nice place to stay.Key West Vacation Rentals are very helpful and easy to reach.The location is perfect just 5 minutes walk to Duval Street and 15 min to...
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    About this property
    Lazy Lane at Shipyard Condos Grab your sunglasses, bathing suit, and sunscreen and get ready to dive into the beach lifestyle when you book this Key West condo. Boasting a shared pool to stay cool, this home gives you the chance to slip into vacation mode with ease. This condo is just two...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Sundown Refuge1 / 23
    (10)Excellent
    0.4 kilometres from Mallory Square
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 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
    Key West Charming1 / 24
    (26)Very good
    0.8 kilometres from Mallory Square
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 January 2016
    The location was awesome, close to everything. We loved that it was close to Blue Heaven. The condo was too small for our liking, but that's not to say that it isn't...
    Reviewed 2 December 2013
    this was a great condo and the location was perfect for the boat races. very clean and everything was just as stated.no problems at all!! and @home in key west were great...
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    About this property
    Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental! Located at the Shipyard Condominiums condo rental in Key West. This downstairs 2 bedroom 1...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.4 kilometres from Mallory Square
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seaport Suite Situated on the second floor of a historic home, this spacious dog-friendly condo welcomes guests with great amenities and a private hot tub! Soak after a long day in the sunshine, and make full use of the back patio space. You're right around the corner from Duval Street's...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    0.6 kilometres from Mallory Square
    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
    Sunny condo w/ entertainment, balcony, & great location near the beach! Dogs OK!1 / 26
    (1)Terrible
    0.2 kilometres from Mallory Square
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Frontier Flat Escape to the land of sea and sun for your next vacation with this fresh condo in Key West. Featuring one bedroom and one bathroom, entertainment, and an awesome location close to all the action on the waterfront, up to four guests will love it here! The family dog is also...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Breezy Bungalow1 / 24
    (3)Very good
    0.7 kilometres from Mallory Square
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Terrace
    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2019
    Breezy Bungalow was a perfect place for the 4 of us. At Home in Key West were very accommodating and pleasant to work with. The Bungalow was clean, pool was perfect and the...
    Reviewed 12 November 2018
    The unit was pleasant enough but needs some attention. It was very badly lit and made it hard for all the occupants to be able to read etc at one time. There was no lighting on...
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    About this property
    Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you! When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Sunrise off Southard- A Tropical Sanctuary Newly Remodeled in May1 / 38
    (1)Excellent
    0.8 kilometres from Mallory Square
    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 kilometres from Mallory Square
    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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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    The Banyan Resort at Key West1 / 6
    (1)Excellent
    0.4 kilometres from Mallory Square
    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
    0.4 kilometres from Mallory Square
    2 Bedrooms, 2 Bathrooms, Sleeps 6 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 6
    Truman's Hideaway1 / 23
    (11)Very good
    0.4 kilometres from Mallory Square
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 December 2013
    The house is old and vert worn. It needs upgraded paint and bedding plus nicer sheets and bath towels. The kitchen was fairly well equipped and adequate but could use updated...
    Reviewed 12 December 2013
    This property has a great location near Mallory Square and many attractions. Truman's Little White House is in your backyard! It needs a few updates and clean up in our opinion...
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    About this property
    It’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch. This lovely Truman Annex condo rental in the...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    0.7 kilometres from Mallory Square
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cool Breeze You will love this charming townhome on the President's Walk in the Truman Annex, Key West's most exclusive gated community in the heart of Old Town. Come for the Spanish tile, then stay for the tropical garden extensive seashell collection. Enjoy the seamless indoor to outdoor living...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Easy Livin'1 / 27
    (1)Excellent
    0.4 kilometres from Mallory Square
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Terrace
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Heated)
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home. The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    0.4 kilometres from Mallory Square
    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
    Four condos w/ entertainment, private parking & beach nearby - great for groups!1 / 24
    (2)Very good
    0.7 kilometres from Mallory Square
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Balcony
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2014
    Lovely we'll maintained, self catering, semi-detached apartments which allows privacy yet accommodates large extended family barbecues and mingling. We hired 3 of the apartments...
    Reviewed 29 July 2014
    Pictures online are great and the property was perfect for 3 families traveling together. We tried not to be in rooms during the day since we were busy with excursions but the...
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    About this property
    Four Flowers Guesthouse Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificing privacy? This complex of four condos is your ticket - featuring entertainment, private parking, and beach access nearby, you'll have everything you could...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    The Dolphin House1 / 23
    (3)Very good
    0.6 kilometres from Mallory Square
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 2014
    The location is perfect for those that want a perfect mix of quiet but close to the action on Duval. The décor was beautiful, pool and outdoors perfect. Great area for grilling...
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    About this property
    Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town. Wonderful for larger groups or family get togethers, The Dolphin House offers a roomy vacation home and quaint guest house with a pool and outdoor living...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Restored historic home w/ private pool & reserved off-street parking - Dogs OK!1 / 24
    (1)Excellent
    0.7 kilometres from Mallory Square
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 2017
    My family and 2 of our friends joined us on this trip. The property was clean and close to absolutely everything. We could not have asked for a better place to stay.
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    About this property
    Bahama Dreaming Start planning your Key West vacation when you book this three-bedroom, two-bathroom home. Up to eight guests will spend their vacation days lounging by the private pool, strolling the streets of downtown, and soaking up the Florida sun on soft sand beaches. The family dog is also...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Bright Shipyard Condo1 / 10
    (1)Excellent
    0.8 kilometres from Mallory Square
    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
    Lavender Jungle1 / 27
    (27)Very good
    0.8 kilometres from Mallory Square
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2018
    My husband and I stayed here last week and was very pleased! We would definitely stay here again in the future and we would recommend this place to anyone. Great location...
    Reviewed 12 June 2018
    Perfect spot. Literally walking distance to the beach to the water park to Duval street to everything . The front had a porch and the back had a deck with a grill and table. Two...
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    About this property
    You are instantly soothed walking through the door of the Lavender Jungle, located in the Truman Annex, one of Key West's most attractive, quiet, and convenient neighborhoods. You’ll quickly see why its moniker fits, when you notice the purplish-pink walls and African art that adorn the living...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.8 kilometres from Mallory Square
    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Curry House Bed & Breakfast Looking for the perfect Key West vacation rental to host your family reunion or corporate retreat? Your search stops with Curry House Bed & Breakfast, a nine-bedroom, nine-bathroom getaway with historic charm, modern comforts, a private swimming pool, and room for up to...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
    Harbor Walk Hideaways1 / 22
    (21)Excellent
    0.4 kilometres from Mallory Square
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
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    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2019
    We loved our stay! We have been trying to find time to visit again. You open the gate from the busy street and it’s literally like you walk into another world. The plants and...
    Reviewed 11 March 2016
    Our party of eight absolutely LOVED this place. Location was to die for and price could not be beat! Just steps from Sloppy Joes, The Green Room and Lagerheads Beach Bar just...
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    About this property
    Very private gated compound sleeping eight guests right in the heart of Key West's Old Town. Enjoy the beat of Key West's nightlife, the romance of sunset at Mallory Square, or the excitement of deep sea fishing or water sports all less than a two-minute walk from our tropical paradise. Standing...
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    Location Information
    Key West, Florida Keys
    Private Room - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    0.6 kilometres from Mallory Square
    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
    Alluring Porches1 / 30
    (18)Very good
    0.6 kilometres from Mallory Square
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Terrace
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2019
    We loved this house. Chose it because of its 3 ensuite bedrooms for a family holiday for my husband and I, our son and daughter in law and our niece. We all loved the privacy it...
    Reviewed 31 May 2018
    Everyone in our group loved the place. It was clean and well stocked with about anything you need. A porch off both bedrooms and a small, secluded deck that was perfect. It's...
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    About this property
    Feel the tropical allure of this spacious home in the center-of-it-all community of the historic Truman Annex! The recently updated 3-bedroom, 3-bath town home, is the tranquil escape you have been looking for. Decorated with Key West charm and unique artwork, stunning orchids surround this home...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    0.8 kilometres from Mallory Square
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Curry House Room 5 Experience a piece of Key West's past when you book a stay at this charming ground-floor suite in the historic Curry House Bed & Breakfast! Up to two guests will enjoy a shared on-site pool, home comforts, and a convenient location in the heart of the city. Curry House sits...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Brand New! Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.1 / 42
    (1)Excellent
    0.8 kilometres from Mallory Square
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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
    Key West Suites Hotel unit 2011 / 16
    (1)Excellent
    0.8 kilometres from Mallory Square
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
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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
    Key West Suites Hotel 2051 / 16
    (2)Very good
    0.8 kilometres from Mallory Square
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 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
    0.3 kilometres from Mallory Square
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
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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
    0.9 kilometres from Mallory Square
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Searching for an affordable monthly vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Then just tune into the Windchime! This lovely studio for two comes with all the comforts you need for an extended stay away from home,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    0.8 kilometres from Mallory Square
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Curry House Room 2 Experience a piece of Key West history when you rent this charming Curry House suite, which features a private en suite bathroom, a semi-private balcony, a shared pool, and room for up to two guests! Located in a quiet neighborhood three blocks from Duval Street, Curry House...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    0.7 kilometres from Mallory Square
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only 1/2 block from the fabulous shops, restaurants and bars that made Duval Street famous. Beautifully furnished and luxuriously appointed, Bahama...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    0.4 kilometres from Mallory Square
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else Old Town Key West has to offer. Step out on the deck of Mary's Trio and breathe in the ocean breeze! This well-furnished home provides plenty of space to relax - ideal for families or...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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