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Holiday Rentals in Key West

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 370 Rentals in Key West
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    BMW Fantasy - 2 Bedroom Condo with a Shared Pool1 / 14
    (35)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    Cleverly hidden from view at the end of a narrow island urban lane that intersects with downtown Duval Street, this Starlight Siesta vacation rental encompasses the rear half of the Key West penthouse property known as Penthouse On Duval. Perfectly staged in the island's city center, this...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Fantasy Resort Villa ~ Weekly Rental1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Parking
    • Satellite TV
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Satellite TV
    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Caroline House Estate ~ Weekly Rental1 / 31
    (7)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Patio
    • Hot Tub
    • DVD Player
    • Air Conditioning
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    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 33040
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Beach Club #408 - Unique Oceanfront living1 / 37
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
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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
    Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths. Enjoy breathtaking views of the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Artist Cottage in Truman Annex1 / 21
    (12)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Truman Annex Best Location in Town!! 2 Bedroom 1 Bath ground floor Shipyard Condo. This beautiful condo sits on a private quiet walking lane and is just a 5 minute walk to downtown where you will find Key West's famous bars and shopping. Also a 10 minute walk to Ft. Zachary Taylor, our beautiful...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
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    • Private Garden
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    Pet friendly
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    Smoking allowed
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    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Deluxe One Bedroom Condo1 / 8
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Air Conditioning
    • Shared Garden
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <BR> KEY WEST VACATION CONDO RENTAL DESCRIPTION<BR><BR> Our beautiful deluxe one bedroom condo in Key West Florida on<BR>Southard Street is just blocks from the ocean and Duval street.<BR>Located in historic old town, the condo is enclosed in a beautiful<BR>garden on the ground floor. It is...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Air Conditioning
    • Patio
    • Ocean Views
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 private bedrooms, plus pullout bed. Immaculate cabin interior. Approximately 100 yards off shore is where your adventure begins! Enjoy key west sunshine on your own private sundeck with comfortable upholstered seating & outdoor table for drinks/snacks. After you've worked on your tan, venture...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Secret Courtyard Cottage ~ Weekly Rental1 / 9
    (6)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Hot Tub
    • Patio
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    • DVD Player
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    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this Secret Courtyard Cottage hideaway, you'll never know you're right in the center of Old Town Key West. Situated at the end of a little walking lane, this charming cottage, with private Jacuzi,  is made...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Harbor Walk Hideaways1 / 22
    (20)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
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    • Grill
    • Porch
    • Air Conditioning
    Suitability
    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 33040
    Private Room - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Key West Spa Villa ~ Weekly Rental1 / 22
    (7)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Pelican Landing Florida Retreat1 / 23
    (32)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Satellite TV
    • Internet Access
    • Grill
    • Terrace
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. Our beautiful waterfront...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Eaton Manor - 2 Bedroom Condo with a Shared Pool1 / 14
    (12)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Balcony
    • Satellite TV
    • Terrace
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. Eaton Manor sits on the north side of LaBrisa and provides easy access to...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pelican Landing St.John Penthouse1 / 20
    (32)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Terrace
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. Our beautiful waterfront...
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    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Pavilion Villa ~ Weekly Rental1 / 20
    (8)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Patio
    • Satellite TV
    • Grill
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    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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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Family Reunion ~ Weekly Rental1 / 45
    (2)Very good
    9 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    • Washer
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    • Grill
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    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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    Key West, Florida Keys 33040
    Holiday Rental House - 9 Bedrooms, 7 Bathrooms, Sleeps 22
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    Pelican Landing Dominica Retreat1 / 21
    (25)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Satellite TV
    • Balcony
    • Internet Access
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Hot Tub
    • Terrace
    • Central Heating
    • Sauna
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps to the Beach and Sunrise Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnished with all of the comforts of home. Large flat screen tv, ensuite bath, full laundry center, fully stocked kitchen, assigned parking bay and...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ann Street Tranquility:  A cozy and peaceful cottage1 / 16
    (49)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Ann Street Gardens1 / 25
    (53)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Washer
    Suitability
    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 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Ocean Views
    • DVD Player
    • Sauna
    • Satellite TV
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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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 4 Quick View
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    • Satellite TV
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    • DVD Player
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    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    6 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Terrace
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    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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    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 15
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    Catherine House: A charming Old Town Key West cottage1 / 22
    (39)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Satellite TV
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    • Patio
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    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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    Island Days: Parking and Pool - Fishing, Boating, Golfing, Dining, Shopping!1 / 29
    (17)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Poolside Townhome - Perfect for family or Travel with Friends! The Best of Everything! 'Island Days' has it all: Large heated resort style pool with Tiki Hut right outside your French doors. Lush landscaping and off street parking steps to your door complete the resort feel all in a...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Tropical ~ Tranquility ~ Weekly Rental1 / 14
    (6)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit old town Key West for the Sunset Celebration on Mallory Square while enjoying entertainment, dining and shopping along Duvall Street...This historical city has much to see & do...Water sports of every kind...Swimming, boating, fishing and much more...or...Just relax at your resort around...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pelican Landing Aruba Retreat1 / 21
    (38)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Balcony
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Balcony
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island...
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    Location Information
    Key West, Florida Keys 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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    • Washer
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Without a doubt, this vacation-defining residence will become as much a part of your holiday memories as the island of Key West itself. Its two-story classic Conch architecture, centrally located in Old Town, includes two spacious master bedrooms, two full en-suite baths, one half bath, a large...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Valhalla1 / 25
    (51)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • 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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The Loft at Echo Gardens1 / 13
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Terrace
    • DVD Player
    • Balcony
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for the perfect Key West get away or corporate retreat? Look no further, here is your opportunity. This little gem is located one block from the world famous Duval Street. This stunning second floor, one bedroom one bath condominium is filled with quality, style and class throughout. The...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Duval Square1 / 69
    (44)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Balcony
    • Satellite TV
    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There's no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens leads to a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Caribbean Cottage ~ Duval Street Key West ~ Weekly Rental1 / 14
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • DVD Player
    • Washer
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pelican Landing St. Kitts Penthouse1 / 19
    (37)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Grill
    • DVD Player
    • Balcony
    • Terrace
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Pelican Landing Bermuda Retreat1 / 23
    (25)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Grill
    • Balcony
    • Satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Duval Square Castaway: A condo steps from the action1 / 15
    (22)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Terrace
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's brick, tree lined courtyard that includes shops and restaurants. These units offer well equipped kitchens and living rooms that open to a patio, or porch, two bedrooms and two baths. There is a shared...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Key West Dreamin' ~ Weekly Rental1 / 16
    (12)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Washer
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pelican Landing Antigua Retreat1 / 23
    (27)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Terrace
    • Satellite TV
    • Balcony
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Parking
    • Air Conditioning
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2 bedroom, 2.5 bath rooftop town home is located within the quaint community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located right in the heart of old town Key West. Park your car in...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Villa Deja vu Key West ~ Weekly Rental1 / 108
    (7)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    HISTORIC KEY WEST  - Conch House - Sleeps 51 / 15
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Satellite TV
    • Air Conditioning
    • Porch
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OVERVIEW The Conch House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (2) twin...
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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 6 Quick View
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    • DVD Player
    • Grill
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Washer
    • Balcony
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    To tee, or not to tee: that is the question ... But whether or not golf is your game, the Key West Golf and Country Club promises a stay in one of the most esthetical residential neighborhoods in the Florida Keys. Beyond the masterfully designed 18 hole golf course, here you’ll enjoy the 200 acres...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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