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Holiday Rentals near Sunset Pier

Duval St, Ocean Key Resort & Spa, Key West, Florida 33040
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    RM 1,743 Average
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    Travellers to Key West are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Villa Nouveau Key West ~ Weekly Rental1 / 19
    (1)Excellent
    0.8 kilometres from Sunset Pier
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    The Hemingway1 / 28
    (27)Average
    0.8 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Sundown Refuge1 / 23
    (10)Excellent
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Key West Suites Hotel unit 2011 / 16
    (1)Excellent
    0.8 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both Duval and Southard Streets....
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    0.8 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ​Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private President's Lane area of the prestigious Truman Annex. Offering exquisite amenities, pool access, and an unbeatable location close to Duval Street, Truman Waterfront Park, and Ft. Zachary Taylor...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Royal Palm1 / 25
    (5)Very good
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 two-bedroom, three-story brick townhouse...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Breezy Bungalow1 / 24
    (3)Very good
    0.8 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Terrace
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    • Balcony
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you! When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.7 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This unique property offers a central location to Key West’s main attractions and everything else the Southernmost city has to offer. With a balcony overlooking Duval Street you can be as much...
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    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    0.7 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Collins offers a central location to Key West’s main attractions and everything else the Southernmost city has to offer. With a balcony overlooking Duval Street you can be as much connected...
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    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    0.4 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Whether you're lounging on the front porch's rocking chair or enjoying a seafood dinner inside, Mary's Backyard Too is your home base for Key West adventures and relaxation. This home's great location and relaxed atmosphere invite you to embrace the island lifestyle. This home is located in the...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Banana Key1 / 25
    (10)Very good
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Impressive. Distinctive. Comfortable. The perfect spot for your tropical get away. This second floor, two bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    The Caroline House Estate ~ Weekly Rental1 / 35
    (9)Very good
    0.5 kilometres from Sunset Pier
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Hot Tub
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    Pet friendly
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    Smoking allowed
    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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    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Truman's Hideaway1 / 23
    (11)Very good
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch. This lovely Truman Annex condo rental in the...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Easy Livin'1 / 27
    (1)Excellent
    0.5 kilometres from Sunset Pier
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Terrace
    • Cable/satellite TV
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    • Balcony
    • Private Outdoor Pool (Heated)
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home. The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    0.3 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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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
    0.4 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Charming condo with large front porch & fantastic location. Great for couples on a weekend getaway or a small group of friends looking to be in the heart of Old Town Key West. Fresh, modern space, and full amenities make Mary's Backyard an excellent choice. You are never far from the water here:...
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    Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    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
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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
    The Dolphin House1 / 23
    (3)Very good
    0.7 kilometres from Sunset Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Private Outdoor Pool (Heated)
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town. Wonderful for larger groups or family get togethers, The Dolphin House offers a roomy vacation home and quaint guest house with a pool and outdoor living...
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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    0.4 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Historic Studio Apartment near Duval Street. A beautiful studio in the perfect spot for your next Florida Keys getaway! This studio has been designed with comfort in mind, offering large windows for natural sunlight and plenty of space to spread out. A full kitchen at your disposal in case you...
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    Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Down Island Digs ~ Weekly Rental1 / 14
    (9)Very good
    0.7 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    0.8 kilometres from Sunset Pier
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Secure Parking
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only 1/2 block from the fabulous shops, restaurants and bars that made Duval Street famous. Beautifully furnished and luxuriously appointed, Bahama...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    0.3 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Best location in Old Town, Steps to Duval St and Mallory Square. Rare private beach and fishing pier. Tiki Hut, Pool and spa, Observation decks. On boardwalk to all casual and more upscale spots. All units renovated with beautiful appointments. One parking spot for stay. Full kitcvhen, large...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.8 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    About this property
    • Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • Over 2000 square feet of porches and decks • Backyard with tropical landscaping, pool & waterfall • Huge roof top sun deck overlooking Duval Street • off-street parking One...
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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.7 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take 20% off any available week in August 2019! Location, Beauty and Comfort! Kokomo Korner has what you are looking for! This upscale home has been meticulously designed with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.4 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Ann Street Gardens1 / 25
    (62)Very good
    0.4 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Brand New! Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.1 / 42
    (1)Excellent
    0.8 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience what is like to live in Old Town at the desirable Historic Seaport. This beautiful home is filled with amazing furniture, artwork and amenities that give you the tropical, old town feel you seek when visiting Key West. The smallest details have not been missed, high thread count...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Truman Treasure1 / 21
    (2)Excellent
    0.8 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 5
    Harbor Walk Hideaways1 / 44
    (21)Excellent
    0.4 kilometres from Sunset Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Porch
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Key West, Florida Keys
    Private Room - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Alluring Porches1 / 30
    (18)Very good
    0.8 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Feel the allure of this spacious home in the center-of-it-all community of the historic Truman Annex! The recently updated 3-bedroom, 3-bath town home, is the tranquil escape you have been looking for. Decorated with Key West charm and unique artwork, stunning orchids surround this home and a...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Key West Wabi Sabi ~ Weekly Rental1 / 31
    (4)Average
    0.7 kilometres from Sunset Pier
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    0.4 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Ocean Views
    • Sauna
    • Waterfront
    • Hot Tub
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WATERFRONT PENTHOUSE with LOFT / 2BR/2BA + GREAT VIEWS OF THE MARINA, OCEAN & HISTORIC SEAPORT 5th FLOOR CONDO RENTAL w comfortable high ceilings / Sleeps 8 / 1 Master King - 2 Guest Room Twins - 2 Loft Twins - 1 Queen pullout / Private Balcony EXCEPTIONAL LOCATION & CONVENIENCE On the ocean at...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    0.7 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Waterfront
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    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 8
    0.3 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Sauna
    • Cable/satellite TV
    • Waterfront
    • Hot Tub
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GALLEON RESORT OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY VIEWS OF KEY WEST HARBOR, SUNSET KEY AND THE GULF OF MEXICO. (These views are also available from the master bedroom, living area and kitchen all day, every day) 4th FLOOR OCEANFRONT...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Rose Treehouse1 / 20
    (13)Very good
    0.5 kilometres from Sunset Pier
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
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    About this property
    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 with balconies off both the front and the...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    0.3 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
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    About this property
    OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING VIEWS OF KEY WEST, SUNSET KEY AND THE GULF OF MEXICO Sleeps 6 / 1 Master King - 1 Guest Queen / 1 Queen pullout / Private Balcony EXCEPTIONAL LOCATION & CONVENIENCE On the ocean at the end of North Front St (literally steps from your...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Our Old Town Key West Term Charter yacht license includes 1 FREE SUNSET CRUISE for a minimum of 3 overnight stays included in the price, walking distance to world class Key West local attractions, water sports, and charter fishing when available, weather permitting as per the captain's...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    A Change in Latitudes - TRUMAN ANNEX1 / 27
    (1)Excellent
    0.8 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    MINIMUM RENTAL REQUIREMENTS due to licensing restrictions; rates go down the longer you stay; deals and specials offered. Quiet end unit located in the Truman Annex. Just steps away from Fort Zachary State park/beach; two blocks from Duval Street and one block from The Green Parrot. Walking...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.4 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    A spacious, airy 3-bedroom, 3-bathroom penthouse at The Galleon Resort & Marina in the Old Historic Seaport in Key West. Available from Saturday March 31 to April 7, 2018. Weekly Rental Only. The first level of the penthouse has a full kitchen and wet bar, with a washing machine and dryer. There...
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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.4 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
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    • Housekeeping Included
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    • Hot Tub
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy an unforgettable & fabulous vacation aboard your private charter yacht on the water! Admiral Marsha & Captain Fred are your hosts. Kayak & swim from yacht. Docked 1 block from Duval St in Old Town. Relax in your spacious, A/C master stateroom, ensuite bath, library/study. From water's...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.4 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    5 Star Hyatt Sunset Harbor Resort Studio Condo with Private Entrance Just Off Mallory Square in the heart of Key West; King Bed with Private Bath; Kitchenette with Coffee Maker, Microwave and Fridge. 1 Block from Duval Street.. Jimmy Buffet Fans Rejoice as this week is Parrothead Week. These...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Bahamian Reed1 / 26
    (1)Average
    0.8 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back to again and again. This two-bedroom, 1.5-bathroom townhome located in scenic Truman Annex in Old Town is conveniently located near all the reasons you came to Key West yet...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Seaport Treasure Estate ~ Monthly Rental1 / 34
    (1)Excellent
    0.2 kilometres from Sunset Pier
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    While you won’t need a treasure map to find this exclusive resort-style estate, you’ll know you’ve discovered a rare island gem from the moment you walk through the private gates. Hidden by white picket fences and mature tropical landscaping, this spacious Seaport Treasure Estate is cleverly...
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    Key West, Florida Keys
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    0.5 kilometres from Sunset Pier
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Hot Tub
    • Ocean Views
    • DVD Player
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    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfectly positioned on Sunset Key, ‘the islands island,’ the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the ‘main island’ of Key West. A splendid view gazing toward Mallory Dock and the famous sunset celebration, this one-of-a-kind waterfront property offers a...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    0.5 kilometres from Sunset Pier
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Classic romantic 1800’s Key West architecture has inspired a superbly executed renovation of this extraordinary historic Victorian estate. Displaying a perfected cosmopolitan flair, the owner / designer has artfully intertwined a look-back into architectural history with a sophisticated...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Kemp House1 / 25
    (22)Excellent
    0.6 kilometres from Sunset Pier
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Best Old Town Location in Key West. Two blocks from Duval Street.1 / 16
    (17)Excellent
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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. There...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Lady Emma1 / 25
    (1)Excellent
    0.8 kilometres from Sunset Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Smoking allowed
    About this property
    There's something special about the kind of comfortable living afforded by this four-bedroom, 2.5-bath, single-family home designated as 'Lady Emma.' The house takes its name from the street it inhabits, one of the most desirable addresses in town. It's part of Truman Annex, an award-winning...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Coral Condo1 / 25
    (18)Very good
    0.8 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Pavilion Villa ~ Weekly Rental1 / 20
    (9)Average
    0.7 kilometres from Sunset Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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