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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 7
    5 of 5 stars (28) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 25
    5 of 5 stars (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    1 / 21
    4 of 5 stars (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Olivia's Flower Unique architecture, a rich history, and a classic Key West neighborhood are just part of the special appeal of Olivia's Flower. This one time flower shop is now a 2 bedroom, one bath, open concept home featuring vaulted ceilings, light drenching storefront windows, a secluded... View all property information
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    Key West, Florida Keys
    1 / 12
    4 of 5 stars (16) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
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    Key West, Florida Keys
    1 / 14
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Key West, Florida Keys
    1 / 14
    4.5 of 5 stars (70) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    SPECIAL DISCOUNTS FOR AUGUST & SEPTEMBER. INQUIRE!!! This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks... View all property information
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    Key West, Florida Keys
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. La Brisa is a two bedroom two bath condo on the third floor. The master bedroom has a king size bed with a walk in closet, a desk... View all property information
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    Key West, Florida Keys
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    This is a House Boat that is 45 feet long and 18 feet wide two story. The Boat House is located Sunset Marina over looking the Gulf Of Mexico. Fisherman paradise and couples paradise. You are just minutes for all of Key West excitement. The marina is very quite and the water is crystal clear. You... View all property information
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    Key West, Florida Keys
    1 / 22
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Plan your Fall getaway! Visit now through OCTOBER 30th 2016 and get a 10% DISCOUNT. Please see our Specials page for all terms and conditions. En Plein Air is a property that was purchased by the owners for its heritage and natural light. An artist lives here in this former general store. Recently... View all property information
    Location Information
    Key West, Florida Keys
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    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Big Coppitt Key near Key West, Florida Big Coppitt Key is located just ten miles from historic Key West. This three bedroom, two bathroom waterfront home is in a pristine location and available for monthly rental of $3,250.00 from May to December 2016. Upscale furnishings. Quiet neighborhood. Dock... View all property information
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    Key West, Florida Keys
    1 / 6
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Perfect for two families wanting to vacation together or large groups. This is a large duplex home with a total of 5 bdrms and 3.5 bathrooms: One side has 3 bdrms (two rooms with queen, one room with 2 twins) + 2 baths. The other side has 2 bdrms (one room with queen, one room with 2 twins) + 1.5... View all property information
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    Key West, Florida Keys
    1 / 20
    4.5 of 5 stars (9) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major renovation to become the  fabulous Penthouse on Duval. This unique private Caribbean style penthouse is the perfect prescription for some lofty relaxation. Perched just above the fun and frolic... View all property information
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    Key West, Florida Keys
    1 / 27
    3 of 5 stars (5) Average
    7 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once authentic and magnificent. If you have ever had the opportunity to stroll the residential streets of the Historic Seaport of Old Town of Key West, you have... View all property information
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    Key West, Florida Keys
    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Live like a local in this Old Town Key West neighborhood. Walking distance to everything you need. Located on one of the best streets in Old Town you are just three blocks from the Harbor Walk….home to the freshest seafood restaurants, waterfront brewery and best happy hours on the island. Walk to... View all property information
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    Key West, Florida Keys
    1 / 46
    4.5 of 5 stars (47) Very good
    10 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    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... View all property information
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    Key West, Florida Keys
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Spacious, tranquil Old Town Key West home. Two bedrooms, 2.5 bathrooms, sleeps up to 7. NOTE: On this page, TripAdvisor is showing our summer price. The price changes seasonally. NEW PRICE FOR APRIL. We are booking monthly renters for April, September, and November, 2016, and April, and... View all property information
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    Key West, Florida Keys
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view of the... View all property information
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    Key West, Florida Keys
    1 / 32
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Key West, Florida Keys
    1 / 18
    4.5 of 5 stars (24) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    CALL AND ASK ABOUT OUR WEEKLY SPECIAL WITH 1 NIGHT FREE! You will love staying in this great Key West historic old town location where 90% of the residents are local. They each have an interesting Key West tale to tell and are a very warm,friendly and diverse group. Here you will absorb the... View all property information
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    Key West, Florida Keys
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    1 / 21
    5 of 5 stars (11) 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... View all property information
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    Key West, Florida Keys
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    30 DAY MINIMUM RENTAL: 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 elegant 2 bedroom unit features a huge... View all property information
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    Key West, Florida Keys
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    30 DAY MINIMUM Two charming Conch houses are joined together at Eliza’s Jewel, an elegant three-bedroom home in Old Town Key West. Located in a quaint neighborhood just steps from the restaurants, shops and art galleries of White Street, Eliza’s Jewel combines beautifully preserved historical... View all property information
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    Key West, Florida Keys
    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    30 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,... View all property information
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    Key West, Florida Keys
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    30 DAY MINIMUM RENTAL This stately home, located in the center of historic downtown Key West, offers up a perfect combination of location, charm, space and privacy. The entrance hallway and staircase are bright and airy, decorated in cool blue tones and exposed Dade county pine. The downstairs... View all property information
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    Key West, Florida Keys
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    30 DAY MINIMUM RENTAL Thompson's Court is the quintessential south Florida home: a sprawling, peach-colored, ranch-style design with large doors and windows that let in the natural sunshine. The large living area is decorated in charming vintage wallpaper and bright, tropical colors. To the left... View all property information
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    Key West, Florida Keys
    1 / 70
    3 of 5 stars (3) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This popular island destination is the site of the only living coral reef in the coastal regions of the US. In addition to the marine life and water activities other features of Key West include natural preserves and unique land animals. Coconut Mallory Resort and Marina is located in Key West,... View all property information
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    Key West, Florida Keys
    1 / 5
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Warm and cozy perfect for a single family with kids Big yard with deck. Going for vacation and looking to rent it for oct dates are flaxeble . Great location to the main street Bikes for guess are available Dates are flaxible, oct is a very besy month in key west , its fantasy fast and most... View all property information
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    Key West, Florida Keys
    1 / 4
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** This cozy upper level unit is perfect for a quiet relaxing week in Key West. Explore the island's history all while being just one block away from Duval Street. This unit is only minutes from attractions like the... View all property information
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    Key West, Florida Keys
    1 / 16
    5 of 5 stars (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    7 day minimum please This fully furnished newly updated getaway is so close to all the local Key West bars & restaurants and museums just take a short stroll or jump on a bike and a way you go... A car is really not necessary in Key west (though parking space for one auto is available) Bike &... View all property information
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    Key West, Florida Keys
    1 / 12
    2 of 5 stars (2) Poor
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Discover paradise of Key West in a distinctive setting. Luxury, two-bedroom, two-bath, (sleeps 4-6) condominium set in a tropical garden with sweeping balconies with views of the Gulf. Your vacation hideaway is decorated in authentic island tradition with fully-equipped modern kitchen, living room,... View all property information
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    Key West, Florida Keys
    1 / 35
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacation rental. The price of a hotel with the comforts of home. Sunrise Suite Key West is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up... View all property information
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    Key West, Florida Keys
    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Private Luxury Home surrounded by lush tropical landscaping. The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district of Key West. Walking distance to all Old Town has to offer, as well as a... View all property information
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    Key West, Florida Keys
    1 / 11
    4 of 5 stars (4) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** CASA ROSA is a classic four bedroom, four bath 'eyebrow' style home located in historic Old Town Key West that is just 1 block of Duval Street and a short walk to Harbor Walk & Mallory Square. This home has a large... View all property information
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    Key West, Florida Keys
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This 2 bedroom, 1 and ½ bath end unit town home is located on President's walk ( Ivory Coast) in the prettiest section of the Truman Annex. The home is decorated in exceptional taste; including a King size bed in the master bedroom with ample closet space and its own private covered deck for your... View all property information
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    Key West, Florida Keys
    1 / 8
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    ATTENTION; July 5 thru Aug 28_ $214.99 - [6-7ntstay] $229.99 [4-5nt stay] For your expediency -- BASE RATES are right here in this paragraph- RATE INFO - See base rates below -over cede RATE SECTION as site has a glitch---not correct in rate section –Read our info here before calling and... View all property information
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    Key West, Florida Keys
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    This elegant two-story island home is a quiet retreat in the heart of Old Town Key West. Margaux's Hideaway is stylishly decorated, perfectly highlighting the classic nature of a Key West home while integrating modern amenities. This home is designed to bring the beauty of the outdoors inside.... View all property information
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    Key West, Florida Keys
    1 / 17
    5 of 5 stars (3) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. Outdoor grill on deck. Please note that I have a licensed real estate broker in Key West who... View all property information
    Location Information
    Key West, Florida Keys
    1 / 3
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
    • Patio
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    'Island Wind' welcomes you to a sun drenched oasis in the heart of Old Town. Charming Bahamian style townhome with tin roof and white spindled porches reminiscent of Old Key West Just a block off Duval Street at the corner of Truman & Simonton in Windward Park a gated community consisting of 13... View all property information
    Location Information
    Key West, Florida Keys
    1 / 28
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    • Patio
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a... View all property information
    Location Information
    Key West, Florida Keys
    1 / 6
    3 of 5 stars (1) Average
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Key West, where a friendly staff member is waiting to welcome you with a freshly baked chocolate chip cookie. Everything you need is available in the hotel, from a 24-hour business center to three meals a day served in the full-service Palm Haven Restaurant. Relax in luxury at our first-class... View all property information
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    Key West, Florida Keys
    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Patio
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    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to the Duncan House - your home away from home in beautiful Key West. The Duncan house is a recently renovated private home with three bedrooms and two baths located in a quiet, Old Town, Key West neighborhood only 10 minutes to Duval Street and only 5-10 minutes to Smathers Beach. 3... View all property information
    Location Information
    Key West, Florida Keys
    1 / 29
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Hot Tub
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    • Waterfront
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Ahoy! PirateHead Cove, your affordable vacation dream-come-true is now taking bookings for 2015/16! Please check the calendar on this site for availability. We do not take partial weeks or bookings of less than 7 nights unless it is between 2 already booked weeks, and ONLY if it shows as... View all property information
    Location Information
    Key West, Florida Keys
    1 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Balcony
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    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance... View all property information
    Location Information
    Key West, Florida Keys
    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    • Internet Access
    • DVD Player
    • Porch
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have been looking for in a vacation rental home. Plenty of space, beautifully furnished... View all property information
    Location Information
    Key West, Florida Keys
    1 / 28
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Parking
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    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire property has been decorated using art from the local galleries and artists. The theme is 'Key West' from scenes around the area including... View all property information
    Location Information
    Key West, Florida Keys
    1 / 21
    1 of 5 stars (1) Terrible
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Internet Access
    • Porch
    • DVD Player
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back to Key West. As... View all property information
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    Key West, Florida Keys
    1 / 26
    3 of 5 stars (1) Average
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Balcony
    • Parking
    • Terrace
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    KEY WEST FOUND – A striking 2 bedroom, 2.5 bath townhome located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. The first floor features open and airy... View all property information
    Location Information
    Key West, Florida Keys
    1 / 1
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Washer
    • Hot Tub
    • Air Conditioning
    • Parking
    • DVD Player
    • Balcony
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View Florida Keys condo for focusing on what is important in life. Enjoy the ocean breezes while unwinding on your private balcony in this tasteful retreat, decorated with your comfort and relaxation in mind. Located on the Atlantic Ocean... View all property information
    Location Information
    Key West, Florida Keys
    1 / 37
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Private Outdoor...
    • Grill
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Key West, Florida Keys