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Holiday Rentals nearby Sunset Pier

Duval St, Ocean Key Resort & Spa, Key West, Florida 33040
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    ₹ 22,489 Average
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    Travellers to Key West are booking December dates now. Secure your holiday home today, and have the perfect trip.
    All 100 Rentals in Key West
    1/2 Block to Duval, World of its own -Nassau Suite1 / 51
    (31)Very good
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Center of It All - Paradise Island Suite1 / 28
    (31)Excellent
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Steps to Duval, Old Town Charm -Grand Bahama Suite1 / 33
    (60)Very good
    0.6 kilometres from Sunset Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Best Location, 1/2 Block to Duval, Bimini Suite1 / 17
    (47)Very good
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Washer
    • Air Conditioning
    • Waterfront
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2018
    The Bimini Suite was perfect in every way. The outdoor backyard and pool were simply amazing. Take a short walk to Duval Street, an even shorter walk to the grocery store and an...
    Reviewed 4 April 2018
    We Love Key West! This location is Awesome! It is Beautifully appointed! The pool and surrounding area are Spectacular! It was Spring Break and the Breaker's were all very...
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    About this property
    Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and convience with new furnitire,...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (55)Excellent
    0.8 kilometres from Sunset Pier
    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 1 week ago
    This is either the second or third time we've stayed here so that should tell you its quality. Beautiful condo with everything you need for a comfortable home away from home...
    Reviewed 26 May 2018
    Joanne and Jim were very nice and helpful! I loved the house and the location is superb! Beautifully furnished and comfortable. My only concern was the lack of hot water in...
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.7 kilometres from Sunset Pier
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MILE ZERO STUDIO (monthly rental): Here's a cozy spot for 1-2 people who are looking for comfort and convenience. Large studio has queen bed and sofa in the living space, full bath, and kitchenette that includes a microwave, dorm refrigerator and full size oven. Ample storage space in kitchen to...
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    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.6 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine the ultimate Key West dream home that feels like a faraway oasis - where you can watch crowning tropical sunsets from a private rooftop deck. Someplace truly extraordinary, elegant yet also comfortable – on a private island surrounded by sparkling turquoise waters and balmy breezes. How...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Royal Palm1 / 25
    (4)Very good
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 February 2018
    This Foundry rental was very clean. The whole place was well maintained. The Foundry is a very spacious and quiet place to stay, close to everything but feels miles away when...
    Reviewed 14 September 2016
    Highly recommend this rental property. Located in a lovely quiet area but 5 minute walk to Duval Street. Fully equipped property could not have asked for anything more. Lovely...
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    About this property
    DISCOUNTED RATES for Open Dates this SUMMER! There's no better way to experience 'Island Time'-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Sunny condo w/ entertainment, balcony, & great location near the beach! Dogs OK!1 / 26
    (1)Terrible
    0.2 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Terrace
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 welcome to join you for...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.5 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Balcony
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.8 kilometres from Sunset Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for a stunning four-bedroom, three-bath vacation retreat with its own private pool, you've found it at Island Style. Located in Truman Annex, Key West's signature gated community, this home has it all: 2,000 square feet in a compact two-story format, porches and balconies, deck...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Casa Havana1 / 24
    (3)Average
    0.2 kilometres from Sunset Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2018
    Location is the best. Casa Havana is 1/2 block off of Duval and 3 blocks from everything in Key West. Deck is great for drink and a cigar in the afternoon and having it own...
    Reviewed 23 February 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group...
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Elegant, upscale home w/ heated pool moments from beach!1 / 29
    (1)Excellent
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Terrace
    • Grill
    • Parking
    • Cable/satellite TV
    • Washer
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Leave behind all of your worries and whisk your loved ones off to this two-bedroom, two-and-a-half bathroom home on Sunset Key! This private island home surrounds you with nothing but natural beauty, gorgeous beaches, and high-quality amenities. Your home is nestled on the private island of Sunset...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Historic house w/ private pool & easy beach access - ideal for groups! Dogs OK!1 / 31
    (1)Very good
    0.4 kilometres from Sunset Pier
    7 Bedrooms, 8 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
    • Internet Access
    • Balcony
    • Grill
    • Washer
    • Cable/satellite TV
    • Parking
    • Patio
    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
    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, seven-and-a-half bathroom house...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 18
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    Alluring Porches1 / 24
    (17)Very good
    0.8 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2018
    Everyone in our group loved the place. It was clean and well stocked with about anything you need. A porch off both bedrooms and a small, secluded deck that was perfect. It's...
    Reviewed 1 November 2015
    Everything as advertised and more. Immaculate, tastefully decorated, roomy. Close to Duval. Porches on each bedroom and off living room. Huge master bedroom with large porch...
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    About this property
    ALLURING PORCHES - A beautiful 2 bedroom 3 bath townhome with an additional den, is the tranquil escape you have been looking for. Wonderfully decorated with Key West charm and unique art work, stunning orchids surround this home and a beautiful open air feel brings the outside in while you just...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.3 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Campbell Suite1 / 23
    (15)Very good
    0.7 kilometres from Sunset Pier
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • 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
    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 starts with the white stucco building that houses this suite and other...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    0.4 kilometres from Sunset Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated on the second floor of a historic home, this spacious dog-friendly condo welcomes guests with great amenities and a private hot tub! Soak after a long day in the sunshine, and fire up the gas grill to make full use of the back patio space. You're right around the corner from Duval...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Restored historic home w/ private pool & reserved off-street parking - Dogs OK!1 / 24
    (1)Excellent
    0.7 kilometres from Sunset Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Parking
    • Washer
    • Internet Access
    • 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
    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 welcome to join...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Foundry on the Waterfront ~ Weekly Rental1 / 20
    (2)Very good
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 May 2014
    The condo was very comfortable and in a great location in being able to walk about anywhere. The only item from the 5th star is the matteresses could be replaced.
    Reviewed 29 November 2011
    This unit was in the perfect location to experience Duval Street and Mallory Square. Close walking distance to everything and yet just far enough away so you do not hear the...
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    About this property
    Located in one of Key West's most striking gated waterfront luxury neighborhoods, Foundry on the Waterfront vacation rental provides a unique opportunity to enjoy a modern condominium, constructed within an important piece of historic American architecture. Situated along the gateway waterfront to...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Rose Treehouse1 / 20
    (7)Very good
    0.5 kilometres from Sunset Pier
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Washer
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 February 2018
    This was a cute second story room with great windows and decks in the front and back. It was the perfect spot for our little get away for our 10 year wedding anniversary, as we...
    Reviewed 14 November 2017
    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...
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    About this property
    DISCOUNTED RATES for Open Dates this SUMMER! 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 occupies the whole second floor...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Breezy Bungalow1 / 24
    (1)Excellent
    0.8 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Terrace
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    Great location - within walking distance of Duval Street, Mallory Square, Hemmingway House, and many other attractions that we visited. The Truman complex, where it is located...
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    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, 2 Bathrooms, Sleeps 4
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    Dog-friendly condo w/ shared pool, full kitchen & parking - central location!1 / 27
    (2)Very good
    0.4 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    The location was fantastic. We were there with a large group and rented out the entire house (including this 2BR/2.5BA main house plus all of the other 1BR guest suites). All of...
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    About this property
    The tranquil majesty of Key West will be at your fingertips when you stay at this homey two-bedroom, two-and-a-half-bathroom condo, with a shared pool and a great location near the beach! Part of Banana's Foster Guest House in the center of downtown, you'll be within easy walking distance from...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Banyan Resort at Key West1 / 6
    (1)Excellent
    0.5 kilometres from Sunset Pier
    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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    Bahama House1 / 24
    (27)Very good
    0.8 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2017
    Bahama House was a wonderful choice for a family gathering and week-long vacation in Key West. Its location in a quiet, short street, a block back from Duval Street, provided us...
    Reviewed 13 April 2015
    We spent Spring Break at the Bahama House and it was perfect for our group. We had 4 adults and 4 teens. Bedrooms were ideal, especially the upstairs room which could fit all...
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    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, 3 Bathrooms, Sleeps 7
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    Kemp House1 / 25
    (20)Excellent
    0.6 kilometres from Sunset Pier
    3 Bedrooms, 4 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 2 weeks ago
    Lovely property within walking distance to all of Key West. Beautiful quiet pool and guest house. Main house has 2 BR with twin beds and queen bed. Guest house has full bed. On...
    Reviewed 17 April 2018
    Beautiful historical house transports you back in time. Loved the second floor back porch for reading and relaxing overlooking the pool.Close to great restaurants and the...
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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, 4 Bathrooms, Sleeps 6
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    Truman Treasure1 / 19
    (2)Excellent
    0.8 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Patio
    • Internet Access
    • Washer
    • Grill
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 October 2017
    Lovely property. I have stayed in the shipyard condo's, that have small rooms and only room for 1 person in the kitchen - this home gave all of my guests plenty of space with...
    Reviewed 28 February 2014
    This three bedroom condo (two upstairs bedrooms with king and twin beds and ensuite baths and a downstairs bedroom with full-sized bed and right-next-door half-bath) exceeded...
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    About this property
    Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    A Place In Paradise1 / 24
    (23)Very good
    0.8 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Balcony
    • Parking
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2017
    The townhouse is in the perfect location. Close to everything. The community is very clean and quiet and the pool, albeit small, was great and just around the corner...
    Reviewed 13 November 2013
    I've been going to KW every year for about a decade and have learned that your home base for the week can be the difference between a good trip and a truly great trip. I've...
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    About this property
    A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in Truman Annex. One of the most desirable locations for vacationers, you will spend your vacation in a quiet gated community surrounded by historic buildings and...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.6 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Parking
    • Terrace
    • Internet Access
    • Air Conditioning
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for pairs of couples and small groups of family or friends, this Key West condo has everything you need to experience the Florida Keys in style. During your stay, sightseeing, a shared pool, and some of America's most beautiful beaches will be on the agenda! Nestled on the western edge of...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Havana Hideaway1 / 25
    (21)Excellent
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 3 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 17 April 2018
    My husband and I stayed at this condo with another couple. The location is absolutely the best and the condo itself was amazing. They had everything set up so you felt like...
    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...
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    About this property
    Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Artist Garden1 / 24
    (27)Very good
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Grill
    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
    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, 2 Bathrooms, Sleeps 4
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    Duval Penthouse1 / 24
    (25)Very good
    0.8 kilometres from Sunset Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Balcony
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2018
    Great time! Will stay there again! People that can't sleep with noise shouldn't have the master bedroom, but it didn't bother us. We enjoyed having the bar next door for the...
    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...
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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, 2 Bathrooms, Sleeps 7
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    0.6 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Balcony
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Townhome, 2 Bedrooms, 2.5 Baths, (Sleeps 4) Available for weekly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful gated Truman Annex community. It’s close to all the major attractions yet just far enough away to be quiet and relaxing. Duval Street,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.3 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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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
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    0.3 kilometres from Sunset Pier
    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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    Key West Found1 / 24
    (32)Very good
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Terrace
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Parking
    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
    KEY WEST FOUND – A striking Key West FL home for rent, this 2 bedroom, 2.5 bath townhome is located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. The...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.6 kilometres from Sunset Pier
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Patio
    • Washer
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DISCOUNTED RATES for Open Dates this SUMMER! Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized brass mermaid sculpture installed in a garden...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    0.8 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LAZY GECKO (monthly rental): This 2-bedroom downstairs condo offers the best of all worlds. Enter from a quiet lane into the newly painted and furnished living/dining/kitchen space. Lots of windows and french doors to let in the sunshine. Master queen bedroom is situated behind french doors...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Easy Livin'1 / 24
    (1)Excellent
    0.5 kilometres from Sunset Pier
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Balcony
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Sundown Refuge1 / 23
    (9)Excellent
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
    • Parking
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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...
    Reviewed 2 March 2013
    Location was great, easy walk to Mallory Square, Duval Street, Beach. Rent bikes, easy to ride to just about anyplace safe and quickly.
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    About this property
    SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in Truman Annex. You'll spend most of your time overlooking Florida Bay in one direction and Truman's Little White House in the other...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    0.4 kilometres from Sunset Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step out on the deck of Mary's Trio and breathe in the beach breeze! This well-furnished home provides plenty of space to relax - ideal for families or large groups. You're within walking distance of the docks, as well as nightlife like Dante's. Stop by Cuban Coffee Queen for a cafécito, and be...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Heavenly Hideout at Rainbow's End ~ Weekly Rental1 / 33
    (8)Excellent
    0.7 kilometres from Sunset Pier
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • 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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    Bloom'n Paradise1 / 24
    (3)Excellent
    0.5 kilometres from Sunset Pier
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2017
    The photos do not impart the beauty of this property. It is perfectly appointed and convenient to Mallory Square and all of Old Town Key West. Jeff is a wonderful host and the...
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    BLOOM'N PARADISE - Relax in luxury in this beautiful Truman Annex private vacation home for rent in the Florida Keys. This property features three bedrooms and three bathrooms in the main house plus a pool house with one bedroom one bath. On Admiral’s Lane in the Truman Annex community, this...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.6 kilometres from Sunset Pier
    12 Bedrooms, 11 Bathrooms, Sleeps 24 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the perfect location to host your corporate retreat, family reunion, or getaway with friends, consider booking this beautiful 12-bedroom, 11-bathroom bed and breakfast. In addition to standard home comforts, you and your travel companions will enjoy the convenience of a...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 12 Bedrooms, 11 Bathrooms, Sleeps 24
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    Harbor Walk Hideaways1 / 44
    (20)Excellent
    0.4 kilometres from Sunset Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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 11 March 2016
    Our party of eight absolutely LOVED this place. Location was to die for and price could not be beat! Just steps from Sloppy Joes, The Green Room and Lagerheads Beach Bar just...
    Reviewed 26 October 2015
    My husband and I, and three other couples came to Key West for a friend's wedding. After much research, I am so thankful to have come across Harbor Walk Hideaways. The grounds...
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    About this property
    Very private gated compound sleeping eight guests right in the heart of Key West's Old Town. Enjoy the beat of Key West's nightlife, the romance of sunset at Mallory Square, or the excitement of deep sea fishing or water sports all less than a two-minute walk from our tropical paradise. Standing...
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    Location Information
    Key West, Florida Keys
    Private Room - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.7 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3000 SF, 3BDR, 2.5BATHS, SLEEPS 6 Treat yourself to a dream vacation in our beachfront residence on the private island of Sunset Key, located in the middle of Key West Harbor. Our tastefully designed upscale villa has beautiful ocean views, private pool, and 2 hot tubs for our guests to enjoy. It...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.4 kilometres from Sunset Pier
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Internet Access
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your Key West vacation in style here at this high-end house with a private hot tub! 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
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    0.4 kilometres from Sunset Pier
    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 a historic estate and renovated with modern conveniences, hardwood floors, and plantation shutters, with plenty of ambient light. This second story unit has a large bathroom and a large deck off the master bedroom for privacy...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Best Old Town Location in Key West1 / 17
    (17)Excellent
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Patio
    • Wi-Fi
    • Secure Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2016
    An absolutely beautiful well equipped holiday rental. The pictures on the website do not do it justice. Great property, great location could not ask for anything more.Lovely...
    Reviewed 14 October 2015
    Location was superb. Staff at Compass / Truman Annex Reality (Michelle) were easy to work with and very accommodating. Owner was very pleasurable and great to work with. Overall...
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    About this property
    Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. Ceramic tile on first floor and all bathrooms. Hardwood floors in bedrooms and stairs....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Down Island Digs ~ Weekly Rental1 / 28
    (9)Very good
    0.7 kilometres from Sunset Pier
    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 30 November 2017
    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 25 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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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