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House Rentals in Key West, FL

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    Travellers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 10
    2.5 of 5 stars (3) Poor
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    1 / 23
    5 of 5 stars (29) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    1 / 32
    5 of 5 stars (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    1 / 20
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    OVERVIEW The Turtle House is a 100+ year old recently completely renovated Conch house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas. The house can be described as... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    4.5 of 5 stars (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The name of this one-bedroom, one full bath condo suggests the most persistent legend of Key West: that vacationers come for a week and stay a lifetime. Located in the prestigious gated Truman Annex community, this unit is the perfect place to try out island living for yourself. From its fabulous... View all property information
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    Key West, Florida Keys
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    What could be more apropos of your next vacation than Jimmy Buffet's famous lyrics "changes in latitudes, changes in attitudes, nothing remains quite the same." It's almost as if he were singing about the Key West residence aptly named "Latitude Adjustment." Featuring two bedrooms, two full baths,... View all property information
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    Key West, Florida Keys
    1 / 17
    4 of 5 stars (43) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our Island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    5 of 5 stars (38) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    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... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This one bedroom loft apartment with full kitchen and laundry has everything you need for an extended stay! Located on one of the best streets in Old Town you are just three blocks from the Harbor….home to the freshest seafood restaurants and best happy hours on the island…or walk to Duval... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 12
    4 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    4 of 5 stars (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.... 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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    Tucked behind a breathtaking tropical garden wall this spectacular Mediterranean Caribbean vacation rental home reflects a dynamic blend of contemporary Mediterranean with Caribbean architectural design. Located along one of Key West's most desirable residential streets this "Casa el Paradiso" most... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Well maintained townhouse in the Truman Annex of Key West. The house has a beautiful garden that you will enjoy. A short walk to Duval and Mallory Square. All quality furnishings. Margaret' s Park is the choice in Key West. Two master suites with private balconies. The house is fully equipped... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    5 of 5 stars (13) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Outdoor Dining Area
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    • Terrace
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    • x
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    • x
    About this property
    Beautiful Poolside Townhome - Perfect for family or Travel with Friends! The Best of Everything! 'Island Days' has it all: Large heated resort style pool with Tiki Hut right outside your French doors. Lush landscaping, off street parking steps to your door, all in a private 3 bedroom 3 bathroom... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4 of 5 stars (55) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. 7 night minimum rental.Paradise is definitely found in this Non-Smoking,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 9
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
    About this property
    Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this Secret Courtyard Cottage hideaway, you'll never know you're right in the center of Old Town Key West. Situated at the end of a little walking lane, this charming cottage, with private Jacuzi,  is made... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4 of 5 stars (15) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
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    About this property
    Solaris Cottage, located on one of Key West most private slow lanes, was built for you. We guarantee that the moment you step onto the front porch and into the cool, sun-dappled living area, your stress will drop away and your creativity will soar. This one-bedroom, one-bath unit is located on a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 stars (3) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 27
    4.5 of 5 stars (15) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Waterfront
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    • ?
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    • x
    About this property
    The M/V Coconuts is a completely unique home with 360 degree water views, it also happens to be a 50-foot trawler, permanently docked at the Key West Harbor Marina. This is more than a boat. It really is a very comfortable home, with proper living area, bedrooms and large sundecks. There is over... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 6
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Over 100 miles from mainland Florida and the southernmost point in the United States, Key West has attracted numerous artists and writers, including Ernest Hemingway, Wallace Stevens, Ralph Ellison, Elizabeth Bishop, Tennessee Williams, Robert Frost, and James Merrill. At 410 Caroline Street is... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    4.5 of 5 stars (26) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 43
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Perfectly positioned on Sunset Key, ‘the islands island,’ the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the ‘main island’ of Key West. A splendid view gazing toward Mallory Dock and the famous sunset celebration, this one-of-a-kind waterfront property offers a... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 stars (21) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
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    • x
    About this property
    This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the exclusive use of compound residents. La Prive has... View all property information
    Location Information
    Key West, Florida Keys
    1 / 17
    5 of 5 stars (20) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around... View all property information
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    Key West, Florida Keys
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Waterfront
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    • Ocean Views
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    • x
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    • x
    About this property
    AVAILABLE FOR STAYS OF 28 DAYS OR LONGER. Vacation in style in this 2 bedroom, 2 bathroom beautifully furnished Keys Home, with lush landscaping with over 20 palm trees, tiki hut/bar with bar stools, heated swimming pool, pool deck chairs, private sandy beach, outdoor deck with dining, outdoor... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 stars (52) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens... View all property information
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    Key West, Florida Keys
    1 / 41
    4.5 of 5 stars (2) Very good
    9 Bedrooms, 7 Bathrooms, Sleeps 22 | Quick View
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    About this property
    Thinking about getting your extended family or friends together for a Key West vacation? This one-of-kind gated Key West vacation rental compound, with large private swimming pool in spacious landscaped tropical garden setting, could be the perfect place. Family Reunion Key West vacation rental... View all property information
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    Key West, Florida Keys 33040
    1 / 41
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Casa Mañana at 800 Virginia Street is perfectly situated for the guest who wants to enjoy Key West at its finest. Located just three blocks from Duval Street, home of world famous watering holes, shopping, and dining, this Old Town jewel is just steps away from Fausto’s Food Palace, Sandy’s Café,... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    5 of 5 stars (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Genuine ‘old-world’ charm meets modern tropical luxury in this wonderful historic island home. Built of original glistening clear heart pine from floor to 12 foot ceiling, the immaculate interior rooms radiate a warm and magical feel that would be nearly impossible to replicate by modern builders.... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    4.5 of 5 stars (7) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach.<BR>This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (16) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere... View all property information
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    Key West, Florida Keys
    1 / 19
    5 of 5 stars (14) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is just past the... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    4.5 of 5 stars (49) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway .The bungalow features an one level open space living/dining area, full kitchen and a spacious bedroom with a king size bed. There is a... View all property information
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    Key West, Florida Keys 33040
    1 / 33
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    1800 Atlantic Condominiums Unit C232 2 Bedroom. Ocean View. Unit C232 is one of the premium rental Condo's in the 1800 Atlantic Complex. Beautifully decorated with higher end furnishings. Top of the line full size fully equipped eat in Kitchen. Dining room area and spacious living room. Both... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Everyone and everything in Key West goes at its own speed, a wonderfully decelerated, human-friendly pace. Locals call it "island time." It's no accident that this beautifully restored 19th century home with four bedrooms and two full baths is named "Island Time" in honor of that low-key feeling.... View all property information
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    Key West, Florida Keys
    1 / 21
    5 of 5 stars (9) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    About this property
    Chick-A-Pea’s Cottage: Located in the gallery district of Key West. The house is steps off of Duval St. near Hemmingway’s house, the Southernmost Point, the Butterfly Museum and great shops, restaurants and bars . The location is quiet & private… yet in the heart of key west The house is a... 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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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Fairwinds at the Foundry is a gorgeous 3 story end unit townhouse in the Foundry section of the Truman Annex. Walking distance to ALL that Key West has to offer! This light and airy end unit is immaculate! Classic and beautiful coastal two bedroom, two and a half bath 3 story townhouse. Enter... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    5 of 5 stars (17) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Private Outdoor...
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    • Outdoor Dining Area
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Historic Old Town Location - Private Pool - Steps from World Famous Duval Street and the Ernest Hemingway Home! Debating between the comfort of a chic hotel and the thrill of more authentic accommodations? You will get the best of both worlds with this cozy 2 bedroom home, currently available for... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Why stay in one room in a hotel when you can have a whole home? This home has 2 bedrooms, large living room/dining room combination that opens to a deck, and it's own reserved parking space. There is a great community pool that has lots of tropical landscaping and an exercise room in the... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (24) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Porch
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket... View all property information
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    Key West, Florida Keys
    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Porch
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    New owners invite you to enjoy this vacation rental aptly named "Seas the Day!" This newly updated 2 bedroom 1 bath first floor condo is located in the Shipyard section of the Truman Annex. If you are looking for a great location central to all that Key West has to offer, look no further! Park... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Outdoor Dining Area
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    • Terrace
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    • Secure Parking
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This delightful sunny, quiet apartment is located across the street from Smathers beach and just a ten minute drive to Old Town. The apartment is set in a large lush tropical garden with two Olympic size swimming tools, tennis court, shuffle board court and outdoor lounging and dining areas, It is... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway's Library, the residence maintains the mystique of the island's most famous author by way of books, pictures, and... 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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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    4.5 of 5 stars (13) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
    • Balcony
    • Waterfront
    • Satellite TV
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    • Patio
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Come stay aboard our FABULOUS houseboat Libra! Docked in one of Key West's most exclusive yacht club marinas, our guests have free access to a host of "members only" amenities including a swimming pool, private beach, tiki bar, fitness facility, sauna, clubhouse, onsite restaurant, free parking and... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Washer
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    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to our unit at Coconut Beach Resort Come stay at a private tropical paradise, completely renovated the last few years yet reminiscent of days gone by, sitting quietly and serenely right on the ocean on the Atlantic side of Key West. Here you will find a blend of old island architecture,... View all property information
    Location Information
    Key West, Florida Keys 33040