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Key West House Rentals

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    1 / 23
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    5 of 5 bubbles (20) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4 of 5 bubbles (16) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    3 of 5 bubbles (8) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (4) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa Grande... View all property information
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    Key West, Florida Keys 33040
    1 / 32
    3.5 of 5 bubbles (2) Average
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Let year-round warm breezes transport you to deep relaxation at this three-bedroom, three-bathroom Key West vacation rental. The home's great amenities include a shared pool, a gym, and plenty of space for up to six guests! This home is located on Stock Island, which is between Key West and Boca... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    About this property
    28 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is truly a wonderful locale... View all property information
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    Key West, Florida Keys 33040
    1 / 45
    4.5 of 5 bubbles (2) Very good
    9 Bedrooms, 7 Bathrooms, Sleeps 22 | Quick View
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    Thinking about getting your extended family or friends together for a Key West vacation? This one-of-kind gated Key West vacation rental compound, with large private swimming pool in spacious landscaped tropical garden setting, could be the perfect place. Family Reunion Key West vacation rental... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building.  Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 19
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This one-of-a-kind Fantasy Resort Villa vacation rental perfectly blends two charming historic cottages right into a little bit of island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard of this extraordinary property just off Upper Duval St. in... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (7) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    About this property
    This perfectly positioned rental with access to a shared pool puts you close to everything in Key West, so bring the whole family for a memorable tropical retreat. Situated in the premiere gated community of Truman Annex, this home is just steps from historic Old Town. The Truman Annex offers... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4 of 5 bubbles (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites. Opposites attract... View all property information
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    Key West, Florida Keys 33040
    1 / 37
    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Key West vacation you have been seeking. Tucked away in one of the most interesting neighborhoods in the historic... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    10% OFF already discounted prices for Open dates MAY - JULY 2017! Please call our office for details. To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    In this case... 'Two is definitely better than One'! A rare set of early 1900's 'twin-cigar maker's cottages' perched on the southern end of famous Duval Street. The Twice As Nice  vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge... View all property information
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    Key West, Florida Keys 33040
    1 / 19
    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    10% OFF already discounted prices for Open dates in MAY & JUNE 2017! Please call our office for details. 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... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 bubbles (3) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    THE DOLPHIN HOUSE: Twice the comfort of and twice the amenities - located in the exclusive Truman Annex. The Dolphin House Key West Vacation Rental is comprised of a bright and open main house and a lovely and bright guesthouse, with a pool and outdoor living space comfortably nestled in between.... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 bubbles (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one... View all property information
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    Key West, Florida Keys 33040
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    1 / 24
    4 of 5 bubbles (27) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    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... View all property information
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    Key West, Florida Keys 33040
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This 4 bedroom 3 bath home is located in Key Haven (mile marker 5) Key West. Key Haven is a quiet neighborhood Great for boating, snorkeling, diving, fishing, biking, walking or just relaxing in the hammocks. Easy boating access to the Gulf and Atlantic (one canal from open water). Just 4 miles... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 bubbles (9) Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    Grande Dame Key West – (The Watson House) vacation rental estate is an impeccably detailed 3-story Classic Folk Victorian home with 7 bedrooms and 7 bathrooms. An award winning renovation of this stately Victorian mansion has achieved an impressive balance of timeless charm, classic elegance, and... View all property information
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    Key West, Florida Keys 33040
    1 / 54
    3.5 of 5 bubbles (2) Average
    11 Bedrooms, 11 Bathrooms, Sleeps 24 | Quick View
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    The Meeting Point – Key West is by-far the most spacious and classically elegant vacation rental property on the island. Situated in the heart of Old Town, there is nothing else like it. If you’re looking for luxury and plenty of room, The Meeting Point is the grandest vacation rental in Key West,... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (46) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 bubbles (7) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get that sense that you’ve been there before? When I first visited this vacation rental house, it happened to me. My mind sparked, the place seemed wonderfully familiar, and I felt an... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 bubbles (7) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 bubbles (55) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real. Extraordinarily secluded and... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    If you’re craving a Key West beach accommodation with a bone fide front-line view to the sea, you know they’re not easy to come by. But in this pretty vacation rental condominium, By The Beautiful Sea, you can instantly gratify this need for sensational vistas from your own vacation rental terrace... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Stay in a beautifully restored Century Old Conch Home by the Southernmost Point, the beach and Duval Street. Enjoy the nightlife of what Key West has to offer without the need to drive or take a taxi. No detail was left undone through- out this home featuring lots of dade county pine and... View all property information
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    Key West, Florida Keys 33040
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Newly available! The Historic Chavez House on Margaret Street! This 3 bedroom 2 bath two story eyebrow house was Built in 1870 and is in the National Register of Historic Places. Newly renovated and very well appointed! Fine linens, gorgeous furniture, ultra comfortable mattresses, and a cool... View all property information
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    Key West, Florida Keys 33040
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Grand Maison on Duval is located in the Gallery District right on Duval Street near the Southernmost Point. The home is just a few blocks away from the Southernmost Beach, night clubs, and tourist areas which makes it a perfect spot to vacation as it is a quick safe walk to everything Key West has... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Petite Maison is a designer Key West Guest Cottage that is located in the Gallery District of Duval Street. It is located on a quiet hidden lane behind Duval Street. Petit Maison is just a few blocks away from the Southernmost Beach, night clubs, and tourist areas which make it a perfect spot to... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Solaris Cottage, located on one of Key West most private slow lanes, was built for you. We guarantee that the moment you step onto the front porch and into the cool, sun-dappled living area, your stress will drop away and your creativity will soar. This one-bedroom, one-bath unit is located on a... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 bubbles (7) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    THE MARGARET SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    About this property
    THE HARRY SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each suite... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    6 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    • x
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    About this property
    Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES consist of four Luxury Vacation Rentals that can be rented together or separately. LOCATED ONE HALF BLOCK FROM DUVAL STREET, this location is perfect for a multi generation family... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Grand Maison and Petite Maison together sleep a total of 12 guests. They boast 6 bedrooms each with its own en suite bathroom. Spacious with plenty of room allowing for large family get-a-ways, reunions, or wedding parties. Great outdoor spaces where friends and family can gather or taking time... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    New owners and wide open availability! It is not too late to come to Key West! Key West Casablanca Too is the perfect get-a-way vacation rental for two! Casablanca Too is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    5 of 5 bubbles (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    About this property
    Historic Old Town Location - Private Pool - Steps from World Famous Duval Street and the Ernest Hemingway Home! Debating between the comfort of a chic hotel and the thrill of more authentic accommodations? You will get the best of both worlds with this cozy 2 bedroom home, currently available for... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    The Poinciana Place Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The second floor unit "Treetop" sleeps up to 2... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    About this property
    The Poinciana Place Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The Garden at Poinciana Place is a cozy and... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    • x
    About this property
    THE BESS SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Recently... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    • x
    About this property
    THE MARTHA SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    5 of 5 bubbles (16) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Absolute Best Luxury Private Weekly Vacation Rental Home on Duval Street In Old Town Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find... View all property information
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    Key West, Florida Keys 33040
    1 / 32
    5 of 5 bubbles (13) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    “Southard Comfort” is true Island living in downtown Historic Old Town Key West. Two story, 3 bedroom, 2.5 bath plus outdoor shower Nancy & Carl welcome you to their Key West vacation home! This established rental is a dazzling property, and we are committed to continuing its reputation of... View all property information
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    Key West, Florida Keys 33040
    1 / 34
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    • x
    About this property
    New owners and wide open availability! It is not too late to come to Key West! Key West Casablanca is the perfect get-a-way vacation rental for two! Key West Casablanca is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a... View all property information
    Location Information
    Key West, Florida Keys 33040