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Vacation Rentals nearby Old Town Trolley Tours Key West

Mallory Square, Key West, Florida 33040
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    Travellers to Key West are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Best Location, 1/2 Block to Duval, Bimini Suite1 / 17
    (38)Very good
    0.5 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    1/2 Block to Duval, World of its own -Nassau Suite1 / 17
    (19)Excellent
    0.5 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Center of It All - Paradise Island Suite1 / 14
    (30)Excellent
    0.5 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Steps to Duval, Old Town Charm -Grand Bahama Suite1 / 11
    (43)Very good
    0.5 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2017
    This place was perfect! We had booked three of the four suites and basically had the pool to ourselves. The Grand Bahama Suite was perfect for the six of us and in a great...
    Reviewed 19 August 2017
    We had such a wonderful time at the Bahama House; built in 1826, this is such a well kept property, with attention paid to every detail. We met the owner who is such an...
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    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable...
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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.1 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have this recently surveyed 150 thousand dollar yacht all to yourself, at safe harbour marina dock ,and get free captained sunset Trip during your stay ,yacht has a large bed in the bow stateroom and two single beds for smaller people in the other ,,perfect for kids in the other stateroom. The...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Casa Havana1 / 24
    (2)Average
    0.2 kilometres from Old Town Trolley Tours Key West
    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 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
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    Alluring Porches1 / 24
    (16)Very good
    0.6 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Terrace
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 2015
    Everything as advertised and more. Immaculate, tastefully decorated, roomy. Close to Duval. Porches on each bedroom and off living room. Huge master bedroom with large porch...
    Reviewed 9 August 2015
    I was a little apprehensive about booking this place because it didn't have many recent reviews, but I am very glad we booked. The price was very reasonable for Truman Annex...
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    About this property
    ALLURING PORCHES - A beautiful 2 bedroom 3 bath townhome with an additional den, is the tranquil escape you have been looking for. Wonderfully decorated with Key West charm and unique art work, stunning orchids surround this home and a beautiful open air feel brings the outside in while you just...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Bloom'n Paradise1 / 24
    (3)Excellent
    0.3 kilometres from Old Town Trolley Tours Key West
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2017
    The photos do not impart the beauty of this property. It is perfectly appointed and convenient to Mallory Square and all of Old Town Key West. Jeff is a wonderful host and the...
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    BLOOM'N PARADISE - Relax in luxury in this beautiful Truman Annex private vacation home for rent in the Florida Keys. This property features three bedrooms and three bathrooms in the main house plus a pool house with one bedroom one bath. On Admiral’s Lane in the Truman Annex community, this...
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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Breezy Bungalow1 / 24
    (1)Excellent
    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Terrace
    • Parking
    • Balcony
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    Great location - within walking distance of Duval Street, Mallory Square, Hemmingway House, and many other attractions that we visited. The Truman complex, where it is located...
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    About this property
    Breezy Bungalow - Weekly Rental When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside breezes to flow openly into Breezy Bungalow. Two levels of...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (49)Excellent
    0.6 kilometres from Old Town Trolley Tours Key West
    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 2 days ago
    We have stayed at Casa Del Sol 2 times, and had wonderful stays each time. Jim and Joanne go out of their way to make sure all instructions are clear and that the condo is in...
    Reviewed 13 June 2017
    Casa Del Sol is a wonderful town house - location absolutely central and within bike/walking to Old Town.All amenities are tip top as was the furniture, porch, bikes etc. They...
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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
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    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located one block off Duval Street in central Old Town, the unit is on an historic estate and renovated with modern conveniences, hardwood floors, and plantation shutters, with plenty of ambient light. This second story unit has a large bathroom and a large deck off the master bedroom for privacy...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Fairwinds: Truman Annex, Parking & Pool, Walk to Shopping Restaurants Beach1 / 28
    (3)Very good
    0.4 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    Our family of 4 stayed here with 2 adult children. We celebrated our daughter's 21st birthday. The home was very convenient to all activities and sightseeing. Very quiet...
    Reviewed 19 September 2016
    This location was a "bucket list" place so we came up with the money to rent it. It was a good place but there were a lot of steps up to the master bedroom and even more...
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    About this property
    Fairwinds at the Foundry is a gorgeous 3 story end unit townhouse in the Foundry section of the Truman Annex. Walking distance to ALL that Key West has to offer! This light and airy end unit is immaculate! The Foundry is a non-smoking community within the Truman Annex. Classic and beautiful...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Down Island Digs ~ Weekly Rental1 / 14
    (9)Very good
    0.5 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This is such a cute and cozy home in a great location! The house is perfect for 3 people or less. The kitchen/den have limited space so it can get crowded with everyone...
    Reviewed 24 January 2017
    We stayed for a week at 508 Bahama St. We were 1 block behind Duval but you would never have known it. The backyard is so peaceful and where we basically lived all week...
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    About this property
    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Dolphin House1 / 23
    (3)Very good
    0.5 kilometres from Old Town Trolley Tours Key West
    4 Bedrooms, 4 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
    THE DOLPHIN HOUSE: Twice the comfort and twice the amenities - located in the exclusive Truman Annex. The Dolphin House Key West Vacation Rental is comprised of a bright and open main house and a lovely and bright guesthouse, with a pool and outdoor living space comfortably nestled in between....
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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Linger Longer1 / 24
    (22)Very good
    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Terrace
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2015
    I am a repeat renter and plan to return next year. Walking distance to everything but in a quiet community off Duval.
    Reviewed 27 April 2014
    This was the first trip to Key West for my husband and I, but we traveled with more experienced Key West-ers who booked the rental. We were pleasantly surprised when we arrived...
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    About this property
    LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath home rental Florida Keys, located in the President's Walk of Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either side of the full bathroom on...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Artist Garden1 / 24
    (27)Very good
    0.3 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2015
    We stayed at the Artist Garden for our triple birthday celebration (3 friends within a week). The house is beautiful. It is located within Truman Annex. And you can seriously...
    Reviewed 10 April 2014
    We enjoyed a 2 week stay in this beautiful house. The location is perfect. We were only a 5 minute walk to Mallory Square and a 10-15 min walk to other favorite restaurants. We...
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    About this property
    ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private Key West house rental located in the prestigious Admiral's Lane neighborhood of the Truman Annex. This property is in the ideal location, walking distance to all Old Town Key West has to offer along with the beautiful beach at Fort...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Bahamian Reed1 / 24
    (1)Average
    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Balcony
    • Parking
    • Wi-Fi
    • DVD Player
    • Terrace
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2017
    This is a middle townhouse unit in the Truman Annex section of Key West. The photos are a true representation of the unit. One bedroom had a king; another had two twins...
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    BAHAMIAN REED: 2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West. Conveniently located near all the reasons you came to Key West: Fort Zachary Taylor State Park , Duval Street shops, galleries, bars and restaurants, and Sunset Celebration. Gourmet kitchen, bright cheery...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations since I am not a real estate salesman or property manager allow me let the photos speak for themselves. My oversized two bedroom, one bathroom condominium is located on picturesque Southard...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.4 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.4 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Ocean Views
    • Sauna
    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GALLEON RESORT PENTHOUSE with LOFT - 2BR/2BA + GREAT VIEWS OF THE GALLEON MARINA, HISTORIC SEAPORT & OCEAN 5th FLOOR CONDO RENTAL / SLEEPS 8 / 1 Master King - 2 Guest Room Twins - 2 Loft Twins - 1 Queen pullout / EXCEPTIONAL LOCATION, CONVENIENCE & CASUAL LUXURY / On the ocean at the end of...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Key West home w/shared pool and just steps from historic Old Town1 / 24
    (1)Excellent
    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Grill
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    • Balcony
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    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly positioned rental with access to a shared pool puts you close to everything in Key West, so bring the whole family for a memorable tropical retreat. Situated in the premiere gated community of Truman Annex, this home is just steps from historic Old Town. The Truman Annex offers...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Easy Livin'1 / 24
    (1)Excellent
    0.3 kilometres from Old Town Trolley Tours Key West
    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
    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance of...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Havana Hideaway1 / 25
    (20)Excellent
    0.3 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    • Washer
    • Balcony
    • DVD Player
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2017
    We just spent a week in this wonderful condo near Mallory Square and a short walk to so many locations in Key West. The condo was quiet, comfortable, very clean, and tastefully...
    Reviewed 14 March 2017
    This was my third time in Key West, and my second time staying in this unit. There's so many beautiful places to stay on the island, but we chose to come back to Havana Hideaway...
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    About this property
    Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    0.4 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size bed and a balcony (resort view). This unit has a brand new kitchenette featuring new wood cabinets, granite countertop and new stainless appliances including a mini-refrigerator,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Crowner's Jewel1 / 24
    (35)Very good
    0.5 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Terrace
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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
    CROWNER'S JEWEL: Experience the finest in vacation home rentals in Key West Florida when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in the heart of the exclusive gated community of Truman Annex. New owner has added lots of upgrades to make you feel welcome in his new home...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.3 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Terrace
    • Internet Access
    • Outdoor Dining Area
    • Shared Garden
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Duval Penthouse1 / 24
    (24)Very good
    0.6 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • DVD Player
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2015
    Love the Duval Penthouse; our second year staying there. Fantastic location, clean, well taken care of. Only one thing I would change... the mattress in the Master bedroom is...
    Reviewed 26 March 2014
    The place was awesome. As everyone says, the back bedroom is a bit noisy being right on Duval and next to Willie T's but still a great place. I found that leaving doors open...
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    About this property
    DUVAL PENTHOUSE -- A large luxury vacation rental in Key West located in downtown Key West. This property has it all, fabulous location, beautifully furnished and plenty of space to accommodate your friends and family. Duval Penthouse is designed after a chic urban flat with an island twist,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Ann Street Cottage: A bright and airy home near Duval Street1 / 24
    (47)Very good
    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2013
    I selected this cottage via computer. The location is excellent for seeing ALL the sights of Key West. This cottage is as represented. The kitchen was spacious and nicely...
    Reviewed 1 August 2012
    The location is excellently placed in Key West. My girlfriend and I were never more than a 15 minute walk to anything that we needed and the kitchen had many of the things we...
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    About this property
    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    A Place In Paradise1 / 24
    (23)Very good
    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2017
    The townhouse is in the perfect location. Close to everything. The community is very clean and quiet and the pool, albeit small, was great and just around the corner...
    Reviewed 13 November 2013
    I've been going to KW every year for about a decade and have learned that your home base for the week can be the difference between a good trip and a truly great trip. I've...
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    About this property
    A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in Truman Annex. One of the most desirable locations for vacationers, you will spend your vacation in a quiet gated community surrounded by historic buildings and...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Bali Hideaway: A studio cottage that's perfect for two1 / 13
    (47)Very good
    0.3 kilometres from Old Town Trolley Tours Key West
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 2016
    Bali Hideaway is perfect in every way! From the modern decor to the lavish lush pool and gardens! My wife and I totally fell in love with the cottage! We would love to own one...
    Reviewed 3 July 2016
    Very quaint home with just enough space for two. Decor makes you feel like you are in Bali and it has everything you need including pool towels. The property is very secluded...
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    About this property
    Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Pavilion Villa ~ Weekly Rental1 / 20
    (8)Average
    0.6 kilometres from Old Town Trolley Tours Key West
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 May 2016
    Stayed with friends and family place need work. A/C in bathroom terrible, none. Kitchen, family room in main house never stayed cool. it says 3 baths 1 is outside beside the...
    Reviewed 17 August 2015
    When we arrived the main house smelled very musty. I immediately cranked the AC units down to 73 to get some of the air dried out. The King bedroom never lost the musty smell...
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    About this property
    A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    0.5 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fully furnished turn-key two bedroom bungalow is the perfect spot to escape the winter weather in tropical Key West! Full kitchen, luxury shower, high ceilings and washer/dryer in unit! Also has a nice little fenced in outdoor space with a picnic table for enjoying the beautiful weather in the...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Ann Street Gardens1 / 25
    (56)Very good
    0.3 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2017
    My husband and I have stayed in several places in Old Town KW. This little spot is a hidden gem. It is quirky KW at its finest! Perfect location for a couple just wanting to...
    Reviewed 11 August 2017
    This place exceeds all expectations! Location is perfect, staff is amazing we will book Year after Year! Thank you Tim, Bill and Sabrina! The Desjarlais family
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    About this property
    (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    President's Walk1 / 24
    (1)Excellent
    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • 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
    PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same location; now it's your turn. President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind. Situated directly in front of one of the community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Bahama House1 / 24
    (26)Very good
    0.6 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Balcony
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 May 2017
    Bahama House was a wonderful choice for a family gathering and week-long vacation in Key West. Its location in a quiet, short street, a block back from Duval Street, provided us...
    Reviewed 13 April 2015
    We spent Spring Break at the Bahama House and it was perfect for our group. We had 4 adults and 4 teens. Bedrooms were ideal, especially the upstairs room which could fit all...
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    About this property
    BAHAMA HOUSE - Location, Location, Location! Totally gorgeous, this spacious house rental Key West is conveniently located on a quiet street in the heart of Old Town Key West around the corner from the fabulous shops, activities, restaurants and nightlife on Duval Street. Luxuriously appointed...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    Key West Wabi Sabi ~ Weekly Rental1 / 31
    (3)Very good
    0.5 kilometres from Old Town Trolley Tours Key West
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    Great house, pool is awesome, location is perfect right next to grocery store and 1/2 block off Duval. Very quaint inside and out!
    Reviewed 28 December 2014
    We stayed here for a week over Christmas with 4 adult kids and had the best time ever. The accommodations were great for 6 of us and we couldn't ask for a better location...
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    About this property
    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.4 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.3 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Balcony
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ann Street Tranquility:  A cozy and peaceful cottage1 / 16
    (49)Very good
    0.3 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 October 2016
    Returning to Ann Street. Such a comfortable bed!!We love the little Ann Street compound with its secluded pool and lush gardens. Tranquility was the perfect size for us two...
    Reviewed 19 September 2013
    Owners were unbelievably nice from the beginning of communication with them! This cottage lives up to its name. I'm pretty sure the maid skips the bathroom when she cleans in...
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    About this property
    This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kemp House1 / 24
    (16)Excellent
    0.6 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2017
    An absolutely fantastic historic home with a wonderful outdoor living area. The covered area was perfect for middle of the day relaxation when we weren't in the pool. The...
    Reviewed 28 August 2016
    This house was perfect for us! It's on a quiet street so there's no street noise but it's close enough to mallory square, shops and restaurants, a little beach with a bar (with...
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    About this property
    This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Heavenly Hideout at Rainbow's End ~ Weekly Rental1 / 31
    (8)Excellent
    0.5 kilometres from Old Town Trolley Tours Key West
    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 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...
    Reviewed 20 February 2017
    If you want to immerse yourself in true Key West charm .. This is a perfect place for you. From the front porch through the front door you enter a world that is rich in Key...
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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
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    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Rose Treehouse1 / 20
    (6)Very good
    0.3 kilometres from Old Town Trolley Tours Key West
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Balcony
    • Washer
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Stayed for 5 nights in October 2017. Great location on a small lane about 1/2 block to Duval. Cute place. Porches on front and back were awesome. Kitchen was well-equipped, and...
    Reviewed 13 June 2017
    The accommodations were perfect! The rooms were beautiful. The 2 decks allowed for whatever you wanted to do. Very close to Duval Street so we could eat or shop without a car.
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    About this property
    End of Year Savings! 10% OFF published rates until December 25th, 2017. Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed, one-full-bath studio that...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has 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
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    Campbell Suite1 / 23
    (15)Very good
    0.6 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Terrace
    • Washer
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2017
    Staying at the Campbell Suite is like coming home. We have plenty of room to relax after a day of seeing the sights of Key West. The location is perfect. We can walk to all of...
    Reviewed 13 December 2016
    We rented this condo for a week from Historic Hideaways. Tim was great to work with. The condo itself is very nice and some upgrades have been made from the photos. It was...
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    About this property
    End of Year Savings! 10% OFF published rates until December 25th, 2017. Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a 'cozy condo hideaway in the heart of historic Key West.' The historic significance is close to home. It...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Admiral's Lane1 / 20
    (21)Excellent
    0.3 kilometres from Old Town Trolley Tours Key West
    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 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...
    Reviewed 12 April 2017
    Great house with all the amenities. Loved that all of the bedrooms had queen or king beds. Outside gathering space was great but wish it had more sun.
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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
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    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Well maintained townhouse in the Truman Annex of Key West. The house has a beautiful garden that you will enjoy. A short walk to Duval and Mallory Square. All quality furnishings. Margaret' s Park is the choice in Key West. Two master suites with private balconies. The house is fully equipped...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    The Caroline House Estate ~ Weekly Rental1 / 31
    (7)Very good
    0.4 kilometres from Old Town Trolley Tours Key West
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2016
    take your own towels as the very few that are there are tiny and paper thin. the clothes dryer didn,t work at all and took till the end of our stay to get it replaced. the oven...
    Reviewed 22 June 2016
    The Caroline House was absolutely amazing! We just loved the layout of the house -- so many areas to comfortably gather. What a wonderful kitchen -- also great for getting...
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    About this property
    This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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