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Key West Vacation Rentals

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    Travellers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 373 Rentals in Key West
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pelican Landing Dominica Retreat1 / 21
    (25)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    This is a beautifully renovated high end luxurious monthly rental at 1800 Atlantic. The moment you walk in you will appreciate the attention to detail. Enjoy the lovely views of the complex and Atlantic ocean from the private balcony. The master bedroom suite has a brand new king size bed. The...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    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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    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 20
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    OVERVIEW The Cigar 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 four (4) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (1) queen...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Paradise Found  2 Bedroom Condo with a Shared Pool1 / 16
    (55)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
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    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. 7 night minimum rental.Paradise is definitely found in this Non-Smoking,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    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. 7 night minimum rental. Paradise is definitely found in this Non-Smoking,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    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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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
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    • Balcony
    • Terrace
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    • Air Conditioning
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    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, 4 Bathrooms, Sleeps 10
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    My Getaway -2 Bedroom Condo with a Shared Pool1 / 15
    (40)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
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    • Internet Access
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great, popular, quiet townhouse in the well-liked Duval Square complex in the heart of Old Town. One off-street parking space per unit. Easy walking distance to all downtown attractions. Bank, convenience store, health club, hair salon and fine restaurants in the complex. Families are...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Private Outdoor Pool (Heated)
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    • Internet Access
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our paradise please enjoy our modern 1400 square foot 2 bedroom 2 bathroom totally renovated condo. This condo is one of the nicest you will find in the complex. There is music available in every room even the master bathroom. We have thought of everything there is even a flat screen tv...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Ocean Views
    • DVD Player
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    • Wi-Fi
    • Hot Tub
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    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, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
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    • Private Outdoor Pool (Unheated)
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Hot Tub
    • Satellite TV
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    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1800 Atlantic Condominiums Unit C433 2 Bedroom 2 full baths Elegant sophistication abound in this fabulous 2 bedroom 2 bath ocean-view condominium at the premiere 1800 Atlantic Condominiums. This property has been totally renovated and no attention to detail has been spared. Tommy Bahama...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** 2 Bedrooms with king size beds, 2 Bathrooms, and a third guest room/office/ with gym equipment. Charming 2 story conch house on a quiet street in Old Town, right between Duval and Higgs Beach! Easy access to...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 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
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    • 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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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Suitability
    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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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Internet Access
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated unit is located just two blocks from world famous Duval Street surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway. The bungalow features an one level open space living/dining area, full kitchen and a spacious...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
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    Pet friendly
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    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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    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
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    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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    • Balcony
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    This property has been totally renovated and features a fantastic roll in custom shower which is fully wheelchair accessible, The property has fantastic sunrise views along the Atlantic Coastline and Smathers Beach. 1800 Atlantic boasts an Olympic size heated pool and bubbling Jacuzzi tub. The...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bella Vita1 / 22
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Cozy, comfortable, affordable. Not to mention a location in the very heart of the Historic District of Upper Duval. That's why this one bedroom/one full bath rental is aptly named Bella Vita, the beautiful life. Located within La Casa de Luces building, Bella Vita features a wrap-around porch, a...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Rose Treehouse1 / 20
    (5)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
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    About this property
    Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed, one-full-bath studio that occupies the whole second floor with balconies off both the front and the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    A Tropical Tradition (Gallup Arms) ~ Weekly Rental1 / 10
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Nestled in one of Key West's original gated "mini-compounds," the Tropical Tradition vacation rental is a spacious 1990's three-story Key West town home providing an island living experience in a traditional tropical style - both inside and out. A lush tropical garden complete with large 40' X 16'...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hemmingway's Retreat1 / 9
    (9)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50", 42", and 27" flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays and Sundays only. Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale resort ambiance. Here is a retreat where you can slow down...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Louisa House: A comfortable four bedroom vacation hideaway1 / 27
    (41)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Duval Square1 / 23
    (44)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Pet friendly
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    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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    Key West, Florida Keys 33040
    Holiday Rental House - 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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    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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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    1 bedroom with king bed. Living room with pull out sofa bed. 1 bath with jacuzzi tub and shower. Washer and dryer in unit. Balconies off of bedroom and living room with marina view. Stainless steel appliances. The Galleon has a heated pool with hot tub. A small private beach. Poolside tiki bar...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Royal Palm1 / 19
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    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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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. <BR><BR>Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Terrace
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    Pet friendly
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    Smoking allowed
    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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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    • Private Outdoor Pool (Heated)
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    • Internet Access
    • Sauna
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through breeze and expansive views of the tropical courtyard. As assigned private parking space will convey with your rental. You can feel secure in our fortress or a property. Key West is...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    New Beach Club unit - Freshly decorated1 / 29
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Parking
    • Internet Access
    • Balcony
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water as few do in Key West. The breathtaking view can be seen as soon as you enter this spacious 2 bedroom condo. It has just been purchased and...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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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
    Classic romantic 1800’s Key West architecture has inspired a superbly executed renovation of this extraordinary historic Victorian estate. Displaying a perfected cosmopolitan flair, the owner / designer has artfully intertwined a look-back into architectural history with a sophisticated...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    • 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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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    On Hemingway's Rounds ~ Monthly Rental1 / 14
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    • Patio
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s...
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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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    • Internet Access
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities...
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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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    • Air Conditioning
    • DVD Player
    • Balcony
    • Terrace
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beach Club #103 - Unique oceanfront living with breathtaking views1 / 38
    (18)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    • Balcony
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This spacious 2 bedroom unit features a large oceanfront balcony accessed...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hermitage South1 / 25
    (7)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Patio
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated Hermitage...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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