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Key West House Rentals

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    193 Matching Rentals in Key WestView all 413 rentals
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    The Caroline House Estate ~ Weekly Rental1 / 35
    (7)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Heavenly Hideout at Rainbow's End ~ Weekly Rental1 / 33
    (8)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    The Hemingway1 / 25
    (26)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Smoking allowed
    About this property
    THE HEMINGWAY -- A beautiful 2 bedroom 2 bath Florida Keys rental home located in the private, gated community of Truman Annex. An ideal location only 2 blocks from famous Duval Street and the attractions of historic Old Town Key West. You can walk or bike to restaurants, nightlife,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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 popular areas which makes it a perfect spot to vacation as it is a quick walk to everything Key West has to...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    About this property
    I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Our beautiful Key West home is located in the quiet charming neighborhood called the Meadows. We are within walking distance to most of the activities offered in historic Key West. There are fabulous restaurants, beaches and water sports only minutes away. The famous Hemingway House and the Truman...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    This 4 Bedroom Key Haven open-water home has it all!! Enjoy the custom in-ground pool, barbeque and dine in at your waterside gazebo. You can relax upstairs in the custom finished open porch which features a beautiful open water view. This home also offers a downstairs porch which includes a bar...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Coral Garden1 / 23
    (27)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this Key West vacation rental offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    President's Walk1 / 24
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
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    Smoking allowed
    About this property
    PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same location; now it's your turn. President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind. Situated directly in front of one of the community...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    A Place In Paradise1 / 24
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Balcony
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    • Terrace
    • Cable/satellite TV
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Foundry on the Waterfront ~ Weekly Rental1 / 10
    (2)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Patio
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    • Washer
    • Cable/satellite TV
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Artist Garden1 / 24
    (27)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Villa Deja vu Key West ~ Weekly Rental1 / 36
    (8)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Newton Street Hideaway: A secluded one bedroom1 / 21
    (2)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Internet Access
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Royal Palm1 / 25
    (4)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Air Conditioning
    • Balcony
    • Secure Parking
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    • Cable/satellite TV
    • Wi-Fi
    • Patio
    Suitability
    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 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Key West Seashell Cottage-1 block to Duval, spa1 / 16
    (42)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Hot Tub
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Forget that 'been there, done that' hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and 'Sunset Celebration'. The original local artwork throughout...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    ~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Heated Pool on Duval St!1 / 45
    (3)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    • Balcony
    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Coral Villa1 / 24
    (11)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CORAL VILLA -- Located right in the middle of the action, Coral Villa is a beautiful Key West Florida townhome with 3-bedrooms in the gated community of Coral Hammock. Just off U.S. 1, across the street from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home in the desirable canal front community of Key Haven. At the end of a quiet street this 3/2 home features a 2010 renovated kitchen, gorgeous enclosed back porch for relaxing, 2 boat lifts on the canal. The home is set deeply off the street for privacy, and has a long driveway for 2+...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    ~ CASABLANCA ~ Gorgeous Cottage w/ Private Pool, Parking, & Tons of Sun!1 / 29
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casablanca is the perfect get-a-way vacation rental for those seeking a good time, but would like to stay a safe distance from all the Duval Street craziness!! 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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Cable/satellite TV
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    • Private Garden
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful, private home is located in a private, small subdivision with about 25 homes all on the open water, Gulf view. Its's a lovely home with 1 bedroom downstairs with a half bath and 2 large bedrooms upstairs with 2 full bathrooms. The master upstairs has a balcony with an exquisite view...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Cable/satellite TV
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    • Ocean Views
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    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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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Key West Casa1 / 24
    (26)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    KEY WEST CASA – Beautiful and spacious Shipyard condo Key West, Key West Casa is one of only a few 3 bedroom 2 bath condos in the Shipyard complex. This great rental property is located in the prestigous Truman Annex community just 2 blocks to famous Duval Street and walking distance to shopping,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Terrace
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    • Private Outdoor Pool (Heated)
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CAPTAINS WHEEL: Take control of your vacation, be the master of your fate. Captains Wheel will not disappoint. Situated on the corner of Southard and Emma Streets in Truman Annex, a most prestigious gated community in the heart of historic Old Town. 2 bedrooms, 2.5 baths; each queen-bed room has...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Central Heating
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    • Patio
    • Waterfront
    • Grill
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property can only be rented by the month. This estate has it all waterfront, luxury,pool,jacuzzi and dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
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    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM RENTAL .... NO PETS ACCEPTED Break away from it all at Escape on Fleming. This comfortable and fresh two bedroom one bathroom apartment is located in the heart of Old Town. Conveniently located near charming Old Town restaurants such as Azur and Cafe Sole, yet off the beaten path,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    ~ CLOUD 9 ~ Lavish Home In Perfect Location w/ Heated Pool & Private Parking1 / 31
    (16)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    About this property
    The Absolute Best Luxury Private Vacation Rental Home by 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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    ~ MARTHA TRUMAN SUITE ~ Luxury Apt w/ Pvt Balcony, Steps to Duval St & Beach1 / 24
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
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    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    28 DAY MINIMUM STAY, PLEASE DO NOT SEND REQUESTS FOR SHORTER PERIODS! Enjoy the amenities of a luxury hotel in the privacy of our home for a fraction of the cost. Located on the sunset side of Shark Key island, a 10 minute drive from Key West. With 2800 sq. ft., three bedrooms, three and a half...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Poinciana House1 / 25
    (47)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Grill
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Air Conditioning
    • Parking
    • Balcony
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MONTHLY RENTAL- 28 DAY MINIMUM Duval Square Delight is located in a quaint town home community just steps from Duval Street. Upstairs there are residential units and a rooftop pool, while downstairs there are shops and restaurants surrounded by cobblestones and mature, tropical landscaping. Duval...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Coral Hammock 34- 3 Bedroom Townhouse with a Shared Pool1 / 23
    (62)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Terrace
    • Balcony
    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coral Hammock is one of Key West gated communities. 55 luxury resort homes with a lavish Pool and lushly landscaped grounds. These custom single family homes recall the romantic charm of old Key West with spacious floor plans, vaulted ceilings, 'Conch' style porches and the traditional metal roof....
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Valhalla1 / 25
    (52)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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
    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 bursting with tropical ferns and palms. A few...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Villa Tropicale: A lush, secluded estate in the Casa Marina District1 / 34
    (15)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
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    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways and wander by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various species of...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    ~ CASABLANCA TOO ~ Cute Cottage w/ Private Hot Tub & Off Street Parking!1 / 26
    (3)Average
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Historic Old Town. This is a spacious vacation rental with the added bonus of off street parking and a private hot tub! Beautifully...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Linger Longer1 / 24
    (22)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath home rental Florida Keys, located in the President's Walk of Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either side of the full bathroom on...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This private ground floor waterfront home is located in the Key Haven subdivision of fine homes. Beautifully decorated with all new furniture, new flat screen televisions, new beds that includes two king size for extra comfort, large open living room with french doors invites in the tropical...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Key West home w/shared pool and just steps from historic Old Town1 / 24
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Grill
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    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly positioned rental with access to a shared pool puts you close to everything in Key West, so bring the whole family for a memorable tropical retreat. Situated in the premiere gated community of Truman Annex, this home is just steps from historic Old Town. The Truman Annex offers...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Catherine House: A charming Old Town Key West cottage1 / 22
    (40)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shopping. Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval & South Streets). The house can comfortably...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Architects Cottage on Quiet Lane in Old Town1 / 27
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
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    • Grill
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    • DVD Player
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Balcony
    • Cable/satellite TV
    • Patio
    • Terrace
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    6 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
    • Terrace
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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    Havana Lane: A classic conch cottage with rustic charm1 / 25
    (31)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Havana Lane hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery, this classic conch cottage embodies the essence of rustic charm while offering modern amenities and style. Centrally located...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    ~ SOUTHARD COMFORT ~ Breathtaking Home w/ Pvt Pool, Parking & Quiet Location1 / 28
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
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    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Family Reunion ~ Weekly Rental1 / 53
    (2)Very good
    9 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
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    • Washer
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 28
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