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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 378 Rentals in Key West
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    Newton Street Hideaway: A secluded one bedroom1 / 25
    (2)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Colony Poolside: A charming bungalow near the historic cemetery1 / 10
    (49)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Balcony
    • Internet Access
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride to all that Key West has to offer. Mermaid's Paradise will not disappoint. Direct ocean front condo that features 1 master suite with a king size bed, jacuzzi and luxurious walk...
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    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Duval Square Courtyard Condo is just steps from the action1 / 23
    (26)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Balcony
    • DVD Player
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined courtyard that includes shops and restaurants. This three bedroom two bath unit is in one of two standalone WALK-UP buildings in the Duval Square complex. You enter a large open living, dining,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxury 2 Bedroom with Full Kitchen - Sleeps 4 - Walk to the Beach & Nightlife1 / 22
    (7)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE MARGARET SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    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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    Fairwinds: Truman Annex, Parking & Pool, Walk to Shopping Restaurants Beach1 / 28
    (3)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Internet Access
    • Satellite TV
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fairwinds at the Foundry is a gorgeous 3 story end unit townhouse in the Foundry section of the Truman Annex. Walking distance to ALL that Key West has to offer! This light and airy end unit is immaculate! The Foundry is a non-smoking community within the Truman Annex. Classic and beautiful...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Treetop Studio w/ Jacuzzi in Old Town, steps off Duval St.1 / 7
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Washer
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Treetop Studio is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Havana Lane: A classic conch cottage with rustic charm1 / 25
    (30)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • 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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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Hot Tub
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you want to connect or reconnect with the island paradise of Key West, this residence, aptly named The Sanctuary, is a dream destination. Its L-shaped architectural design centers around a temperature-controlled pool, built-in hydro massage spa, graceful waterfall, and outdoor rain shower....
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Poinciana House1 / 25
    (47)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Grill
    • Satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    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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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Amelia Home - Live Just Like A Local - Key West1 / 37
    (3)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Private Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Key West vacation you have been seeking. Tucked away in one of the most interesting neighborhoods in the historic...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pelican Landing Bonaire Retreat1 / 22
    (22)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Satellite TV
    • DVD Player
    • Balcony
    • 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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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Key West Wabi Sabi ~ Weekly Rental1 / 31
    (2)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof....
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Hemmingway's Retreat1 / 9
    (9)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    • Washer
    • Hot Tub
    • Patio
    • Balcony
    • DVD Player
    • Terrace
    • Grill
    Suitability
    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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    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 20
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Porch
    • Washer
    • Grill
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Potter`s Cottage: Sleeps 5, Walk to the Beach & Nightlife, Private Dip Pool!1 / 29
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic Old Town Location - Private Pool - Steps from World Famous Duval Street and the Ernest Hemingway Home! Debating between the comfort of a chic hotel and the thrill of more authentic accommodations? You will get the best of both worlds with this cozy 2 bedroom home, currently available for...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Twice as Nice ~ Weekly Rental1 / 17
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
    • Air Conditioning
    • Patio
    • Satellite TV
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In this case... 'Two is definitely better than One'! A rare set of early 1900's 'twin-cigar maker's cottages' perched on the southern end of famous Duval Street. The Twice As Nice  vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    Amenities & Details
    • 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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    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Balcony
    • 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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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Sauna
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Coastal East – C231 After a recent remodel of the kitchen and bath, this unit underwent a total makeover with its new owners. From new interior design work and furnishings, courtesy of Royal Furniture of Key West, to new closets, drapes and local art, includes works from the gallery of Alan...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Satellite TV
    • Patio
    • 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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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    Suite Dreams in Key West1 / 13
    (1)Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    • Grill
    • Balcony
    • Satellite TV
    • Patio
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our unique property consists of 3 suites (a total of 7 bedrooms and 6 baths) with 2 sparkling lagoon style dipping pools in one compound in the luxurious Casa Marina area of Old Town Key West. We can accommodate groups up to 18 guests. The breakdown of the 3 suites which are being rented...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 18
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Parking
    • Washer
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open onto the 40 ft private balcony that has views of the nature preserve and Atlantic ocean. Fully equipped with all the modern conveniences you would need for an enjoyable vacation....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    La Prive1 / 25
    (22)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the exclusive use of compound residents. La Prive has...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Patio
    • Satellite TV
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below are shops, cafes and a health club offering daily memberships. Secured parking for one car. Three blocks to the nearest beach. Families are welcomed...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Truman Treasure1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Internet Access
    • Washer
    • Grill
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Amelia's Hideaway ~ Weekly Rental1 / 23
    (9)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Parking
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    "In-the-know" travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Internet Access
    • 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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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Parking
    • Grill
    • Washer
    • 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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    • Balcony
    • Private Outdoor Pool (Heated)
    • Sauna
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Admiral's Lane1 / 24
    (21)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Satellite TV
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    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Balcony
    • Internet Access
    • DVD Player
    • 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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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. 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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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • DVD Player
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    Pet friendly
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    About this property
    CONDO HAS A VIEW OF THE GULF OCEAN. THE CONDO BALCONY THAT SEAT 6 PEOPLE. THE CONDO HAS A WASHER AND DRYER AND A FULLY EQUIPPED KITHCEN. THE CONDO IS 960 SQ FT. TELEVISION IN LIVING ROOM AND EACH BEDROOM. HAS BEEN NEWLY REMODELED. 1 BLOCK FROM DUVAL ST. WITHIN WALKING DISTANCE TO ALL...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 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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    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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    3 BR (4bed) 2 BA Luxury Yacht-Sunset Cruise avail1 / 18
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
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    • Waterfront
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 10 days please contact us for reduced rates! Cruises can be added on for additional fee. Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Grill
    • Satellite TV
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GALLEON RESORT MARINA PENTHOUSE with LOFT - 2BR/2BA RENTAL OVERLOOKING SEAPORT MARINA 5th FLOOR SUITE RENTAL / $3,750 (SLEEPS 8) / F-53 / ***Only available Week 2 - Jan 13-20, 2018 / 1 Master King - 2 Guest Room Twins - 2 Loft Twins - 1 Queen pullout EXCEPTIONAL LOCATION & CONVENIENCE (2 blocks...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pelican Landing Harbor Island Retreat1 / 23
    (30)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Balcony
    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 6
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    Newly remodeled family home with a shared swimming pool and fitness center!1 / 32
    (2)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Balcony
    • Washer
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    • Terrace
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let year-round warm breezes transport you to deep relaxation at this three-bedroom, three-bathroom Key West vacation rental. The home's great amenities include a shared pool, a gym, and plenty of space for up to six guests! This home is located on Stock Island, which is between Key West and Boca...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    A Touch of Bermuda in Key West1 / 19
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEWS BULLETIN. JUST HAD A BLOCK OF WEEKS OPEN UP FOR THE WEEKS OF AUGUST 19 TO OCTOBER 21 IN MY OTHER CONDO FIVE DOORS DOWN FROM MY COTTAGE THAT WILL ACCOMMODATE UP TO 4 PEOPLE SO I WILL DO RIGHT BY YOU WITH THE RATE. Now onto my cottage.. Envision yourself unwinding and getting into the casual...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 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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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Balcony
    • Washer
    • Sauna
    • Internet Access
    • Grill
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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