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Holiday Rentals in Key West, FL

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    Travellers to Key West are booking February dates now. Secure your holiday home today, and have the perfect trip.
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ATLANTIC PARADISE -- Imagine the ocean only several yards from your balcony, in a secure gated complex, with all the amenities you could ask for -- pool, Jacuzzi, tennis courts, parking garage with personal parking space. That's what you'll find at Atlantic Paradise. Two spacious king bedrooms,... View all property information
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    Key West, Florida Keys 33040
    1 / 13
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Beautiful, newly remodeled, canal front home with heated swimming pool. Modern kitchen, large open living area with lots of windows that overlooks swimming pool. Backyard is very private, master bedroom also opens to covered porch and swimming pool. Bring your boat, concrete seawall for dockage.... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Ocean Views from Every Balcony. Expect every Amenity from Hyatt. Come Relax by the water with a cool drink. Come visit Old Town Key West for the Sunset Celebration on Mallory Square while enjoying the entertainment, dining and shopping along Duvall Street. This historical city has much to see &... View all property information
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    Key West, Florida Keys 33040
    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 might be showing the summer price. The price changes seasonally. We are booking **monthly** renters for May, September, and November and perhaps the first half of December,... View all property information
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    Key West, Florida Keys 33040
    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 / 20
    5 of 5 bubbles (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    HOLIDAY SPECIAL! 10% OFF Through DECEMBER 30th! 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... 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
    Location Information
    Key West, Florida Keys KEY WEST FL 33040
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    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 33040
    1 / 33
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    28 Night Minimum - Monthly Rentals Only LUXURY Vacation Home located on Millionaire’s Row in Historic Old Town Key West We guarantee that this home will fulfill even the highest expectations. Just under 2000 square feet of indoor living area: This beautiful home is filled with amazing local... View all property information
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    Key West, Florida Keys 33040
    1 / 94
    4.5 of 5 bubbles (47) Very good
    10 Bedrooms, 6 Bathrooms, Sleeps 22 | 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 33040
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    5 of 5 bubbles (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 33040
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    5 of 5 bubbles (1) Excellent
    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 33040
    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 33040
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Just steps away from putting your toes in the Ever dream of waking up, walking out your back door and taking a peaceful morning kayak trip or afternoon stand up paddleboarding? This home is unique in that it not only has a private heated swimming pool, but it also has a put in for your kayak or... View all property information
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    Key West, Florida Keys 33040
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    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 33040
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    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 33040
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    4.5 of 5 bubbles (25) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    CALL AND ASK ABOUT OUR WEEKLY SPECIAL WITH 100 OFF. 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 ambiance... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 27
    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 33040
    1 / 10
    5 of 5 bubbles (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 33040
    1 / 21
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    7 day minimum please Key West Vacation Rental This fully furnished newly updated getaway! It is so close to all the Beach, our pool and the local Key West bars & restaurants and museums just take a short stroll or jump on a bike and a way you go... Our gated pool is climate controlled with plenty... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    "TEE BY THE SEA" vacation rental (we include 7 bikes free for our guests!!!) If you love...GOLF, SPORT FISHING/BOATING, ART/THEATER AND FANTASTIC LIVE ENTERTAINMENT...than you'll love "Tee by the Sea". We're less then 1/2 mile outside of Key West, located in Stock Island. We are 4 1/2 miles... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    This is a brand new listing to VHR! We are running a JUNE SPECIAL DISCOUNT!! The Rooster Retreat along with my attention to detail and welcoming our guest has earned over 30 5-STAR ratings (Listed with another vacation site). Come stay at the Rooster Retreat for your own retreat - it is a... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    2 of 5 bubbles (2) Poor
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Discover paradise of Key West in a distinctive setting. Luxury, large two-bedroom, two-bath, (sleeps 6) condominium set in a tropical garden with a large balcony. Your vacation hideaway is decorated in authentic island tradition with fully-equipped modern kitchen, living room, dining area and... View all property information
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    Key West, Florida Keys 33040
    1 / 35
    5 of 5 bubbles (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 33040
    1 / 15
    5 of 5 bubbles (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 33040
    1 / 21
    4 of 5 bubbles (5) 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 four bedroom, four bath classic "eyebrow" style home located in historic Old Town Key West. This home is just 1 block off Duval Street and a short walk to Harbor Walk & Mallory Square. Enjoy Simonton... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Make your next Key West vacation on the Lion's Paw, a roomy monohull sailboat located in Key West premier marina resort - the Key West Harbour Marina. Three night to seven day vacation packages have options for half day, full day, and overnight sails. The yacht club has it's own private beach and... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Welcome to Paradise a lovely place to call home for a month* or more in Key West! Just minutes from the excitement of Duval Street, the NY caliber plays at The Waterfront Theatre, exceptional fishing and swimming in the turquoise waters … Yet nestled in the serene environment of the KW Golf Club... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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. Ceramic tile on first floor and all bathrooms. Hardwood floors in... View all property information
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    Key West, Florida Keys 33040
    1 / 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Nestled behind hisbiscus and stands of bamboo Lone Palm welcomes you to a tropical oasis in the heart of Old Town. Located just a block off Duval at the corner of Truman & Simonton in Windward Park a gated community consisting of 13 privately owned homes around a sparkling 20 x 60 ft. pool; a... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    ISLAND WIND: 2 bedroom, 2 bath Bahamian-style townhome, with tin roof and white spindled decks. Snuggle into an oh-so-comfy king bed in the Master bedroom upstairs; bathroom is ensuite. Guest bedroom downstairs with 2 twin beds; bathroom ensuite with entrance from the kitchen. Open floor... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    I just REOPENED WINTER 2017 dates starting in Feburary! The completely renovated Shabby Chicken - come stay with the large and proud newest bird in town!! 5-STAR rating and the best floor plan around. This ground floor, exceptional, OVERSIZED floor plan with lots more room is only offered in 2... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 33040
    1 / 31
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • DVD Player
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Washer
    • Waterfront
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    We are hosting art workshops and classes! All accommodation, instruction and materials* provided. Workshop retreats are a minimum of 7 days (more days if desired), basic and intermediate levels available. You choose your level of instruction and the number of 3 hour classes you want while you're... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Patio
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • 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 33040
    1 / 21
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    • Internet Access
    • DVD Player
    • Porch
    • Satellite TV
    Suitability
    • 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 33040
    1 / 28
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Parking
    • Balcony
    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • DVD Player
    • Satellite TV
    Suitability
    • 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 33040
    1 / 21
    1 of 5 bubbles (1) Terrible
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • 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
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    3 of 5 bubbles (1) Average
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Air Conditioning
    • 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 33040
    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 33040
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Waterfront
    • Washer
    • Satellite TV
    • DVD Player
    • Patio
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    OVERVIEW: Monthly Only. Right in Key West -- NOT the upper keys. MONTHLY RENTAL ONLY. Swimming pool, Right on the water. Salt water fishing on location. Sea Kayaks on premises. Salt pond tours on premises. Swim with manatees on premises. Ping pong table. 7 doors down from Jimmy Buffett's... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 70
    2.5 of 5 bubbles (4) Poor
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Balcony
    • Shared Outdoor Pool...
    • Hot Tub
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 54
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
    • Grill
    • Private Outdoor...
    • DVD Player
    • Washer
    • Internet Access
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Porch
    • Internet Access
    • Grill
    • Washer
    • Air Conditioning
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Coastal on Coral is located in the beautiful gated community of Coral Hammock on the Quiet end of Key West on Stock Island.This home has all the amenities of a house and a resort combined boasting 3 bedrooms,all with 40"flat screen televisions and each with it's own full bath.A 55"smart television... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Internet Access
    • Washer
    • Balcony
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to start your day of... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Patio
    • Washer
    • Terrace
    • Ocean Views
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Oceanview Secluded Private Two Acre Estate” A PRIVATE TROPICAL PARADISE ON THE ATLANTIC OCEAN. WHITE IBIS INN - LOCATED IN SUMMERLAND KEY ONLY A 15 MINUTE DRIVE FROM KEY WEST OR THE WORLD-FAMOUS BAHIA HONDA BEACH. Sometimes we run a special discounted price from our White Ibis Inn. If you are... View all property information
    Location Information
    Key West, Florida Keys 33040