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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 323 Rentals in Key West
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Conch Haven Old Town 1/1 MONTHLY Rental1 / 12
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Cable/satellite TV
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sunny View1 / 24
    (2)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Lovely 1 bed/2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street. SUNNY VIEW - Adorable, affordable, and a great location! You bet! Sunny View is the monthly rental Key West perfect escape for a couple or singles looking to get away from it...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Walk Everywhere, A TRUMAN ANNEX CONDO! 2 PATIOS, POOL,WIFI,PARKING & BIKES1 / 33
    (11)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Balcony
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    Billy's Blue Heaven is fresh, clean and Pristine. Just a two minute walk to Duval Street and only 300 steps to the world famous Ricky's Blue Heaven Restaurant. The balcony overlooks Truman Annex 's lush landscaping beside the shared swimming pool. A very short walk or bike ride to Fort Zachary...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Real World MTV House Key West1 / 247
    (49)Very good
    10 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    • Waterfront
    • Hot Tub
    • Private Outdoor Pool (Heated)
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    About this property
    THIS ISN'T JUST A HOUSE, THIS IS YOUR OWN PRIVATE MINI RESORT IN KEY WEST, FLORIDA. THIS IS THE PROPERTY USED BY MTV TO FILM THE 2006 REAL WORLD KEY WEST. 500 FEET OF OCEANFRONT, 8 to 10 BEDROOMS are available (sleeps up to 20) , 5 1/2 baths, 11 plasma TVs, pool table (and Ping Pong), tennis...
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    Key West, Florida Keys 33040
    Holiday Rental House - 10 Bedrooms, 6 Bathrooms, Sleeps 22
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    LOCATION! Feel like a local! Treetop Studio w/ Jacuzzi steps off Duval St.1 / 7
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    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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    Emma's Escape1 / 23
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street. Emma’s Escape (monthly rental): Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Terrace
    • Balcony
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    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes. BOGEY'S RETREAT (monthly rental): Welcome to Bogey's Retreat, your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows you to...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations since I am not a real estate salesman or property manager allow me let the photos speak for themselves. My oversized two bedroom, one bathroom condominium is located on picturesque Southard...
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    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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    • Patio
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    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Spectacular Atlantic Ocean View Condo (MONTHLY)1 / 26
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Ocean Views
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    • Waterfront
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    Pet friendly
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    About this property
    ************************************************************************************************************************ NOTE: We are currently accepting only monthly rentals (28 days or longer). Please inquire for a quote....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anchor Drop Key West A3071 / 55
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anchor Drop A307 is a totally renovated top of the the line unit. King bed in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room. Anchor Drop is beautifully renovated and decorated by an interior designer. Custom bathrooms and modern kitchen with...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West home w/shared pool and just steps from historic Old Town1 / 24
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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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, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
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    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Terrace
    • Ocean Views
    • Sauna
    • Hot Tub
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flair. Full kitchen with all...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Place In Paradise1 / 24
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Wi-Fi
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    • Balcony
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE! A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in Truman Annex. One of the most desirable locations for vacationers, you will...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
    About this property
    Private outdoor kitchen to able to enjoy cooking your favorite dish while enjoying the large outdoor space. HIDDEN TREASURE (monthly rental): You could easily pass by this jewel of a home without ever knowing it was there. Located down Wong Song Alley behind a private fence, just a few steps from...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Breezy Bungalow1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Terrace
    • Parking
    • Balcony
    • DVD Player
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you! Breezy Bungalow - Weekly Rental When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Verandah1 / 24
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    About this property
    Beautifully designed yet comfortable private home that you may never leave, only to go outside to your private pool and secluded space to hang out. VERANDAH (monthly rental): - Tucked away on historic Frances Street lies your island escape… Verandah is a stunning monthly vacation rental -- two...
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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 6 Quick View
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    • Patio
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    • Ocean Views
    • Washer
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    • Cable/satellite TV
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This yacht is very spacious and bright with windows surrounding it making views of the ocean amazing. The marina and its grounds are meticulous and located in the middle of a turquoise paradise with amazing water clarity. Your stay will include free access to the marina's private pool,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'. This two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch Plasma...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Duval Balcony - Street Suite1 / 15
    (3)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    • Housekeeping Included
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    Pet friendly
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    About this property
    Located in the middle of Duval St, you are a 15 minute walk in one direction to the Atlantic Ocean and the Southernmost Point, and the same distance to the Gulf of Mexico and Mallory Square. Shopping, nightlife and the best restaurants are outside your front door. Hemingway House is 2 blocks away!...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Siesta Bay1 / 25
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 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
    Here is your perfect opportunity to enjoy your stay in one of the most popular complexes of Key West, Truman Annex! SIESTA BAY -- Beautiful two bedroom one bath upstairs Key West condo rental in Truman Annex, just steps away from the shared pool and within walking distance of anything you'd...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Wind Swept1 / 24
    (2)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Terrace
    • Private Outdoor Pool (Heated)
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    About this property
    Screened porches up and down for you to enjoy the the extra living space in this lovely townhome. WIND SWEPT: Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. This lovely 2...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Emma's Secret1 / 22
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens. Emma's Secret (Monthly Rental) Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life. A...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH1 / 61
    (7)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Porch
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    • Shared Outdoor Pool (Unheated)
    • Waterfront
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    About this property
    La Dolce Vita is just steps to Duval Street! 'La Dolce Vita' is beautiful and is a totally renovated condo. Please check out our calendars for availability, photos and video. Everything is brand new from floor to ceilings! 14 foot high ceilings with back lit crown molding in every room...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Rose Treehouse1 / 20
    (7)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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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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    The Banyan Resort at Key West1 / 6
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
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    • Outdoor Dining Area
    • Shared Garden
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Bella Vita1 / 22
    (7)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
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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 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    This wonderful property has brand new living and bedroom furniture in 2016, King bed in the master bedroom, 2 twins in the 2nd bedroom and a memory foam luxury queen sleeper in the living room will comfortably accommodate your party. Watch the sunrise from your private balcony. Enjoy the balmy...
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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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    • Washer
    • Ocean Views
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you have had your fill of hotels and the street scenes of downtown Key West and you don't want to spend another minute on a boat loaded with people but do want to get out on the water, then S/V Tortuga may be the perfect solution for you. Tortuga Sailing Adventures offers a unique, totally...
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    Location Information
    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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    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Terrace
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
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    Steps away from the large lagoon style pool surrounded w/lush tropical landscape. KOKOMO (monthly rental): Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    HISTORIC KEY WEST  - Conch House - Sleeps 51 / 21
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
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    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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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bed 2 Bath Waterfront Key West Condo on Smathers Beach Peaceful views and tropical breezes of the natural salt ponds, acting as a bird sanctuary for native species, will help you relax in a fully furnished and updated 2 bedroom / 2 bathroom property sitting on Smathers Beach in Key West, Florida....
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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 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    A convenient hideaway for your Key West and Lower Keys adventures, this two-bedroom condo is tucked into a quiet complex near shopping, bars, live music, beaches, and Mallory Square. Cozy, fully-appointed rooms include everything you'll need for your Key West vacation but your own clothes. With...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    President's Walk1 / 24
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Grill
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    • Balcony
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    Pet friendly
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    About this property
    Large outside deck invites you to just unwind after a long day of exploring with a good book and a glass of wine or enjoy it with friends grilling your fresh catch PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same location; now it's your turn....
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Imagine the ultimate Key West dream home that feels like a faraway oasis - where you can watch crowning tropical sunsets from a private rooftop deck. Someplace truly extraordinary, elegant yet also comfortable – on a private island surrounded by sparkling turquoise waters and balmy breezes. How...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Waterfront
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    • Ocean Views
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    Pet friendly
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    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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    Key West Charming1 / 23
    (26)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental! KEY WEST CHARMING at the Shipyard Condominiums condo rental in Key West. This downstairs 2...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Mermaid's Garden1 / 24
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
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    Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized brass mermaid sculpture installed in a garden bursting with tropical ferns and palms. A few...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 27
    (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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    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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    Flagler Station1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying. FLAGLER STATION (monthly rental): This one is a priceless gem in a true established residential neighborhood in midtown Key West! Flagler Station was...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Make this your Key West Vacation home! Cozy 2 bedroom, 1 bath home set on the back half of a residential lot with new kitchen, bath, and furniture. Privacy provided by the fenced outdoor area, with a shaded porch and furnished gazebo for relaxing. The location is 5 minutes max to anywhere on the...
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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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    • Air Conditioning
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    • Sauna
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    Pet friendly
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    Smoking allowed
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    Poolside Breeze is a nicely decorated two bedroom 1st floor condominium with an excellent location very close to the pool. Poolside Breeze has an extra large floor plan with an extensive private balcony. Both bedrooms and the living room feature sliding glass doors that open on to the private...
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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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    Beautifully restored private cottage located in Old Town Key West. GREEN ORCHID (monthly rental): Have you been dreaming of living like a local in Key West? Your dream can come true. Green Orchid offers a true Conch Cottage experience on a narrow lane in one of the last historic Old Town...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
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    LAST MINUTE DEAL FOR NEXT WEEK (JAN 13-20, 2018). RATE DROP OF $200 FOR THE WEEK. BASE RENT IS NOW $1400. The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Kemp House1 / 25
    (20)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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