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Holiday Rentals in Key West, FL

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 9
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Studio, Sleeps 2 | Quick View
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    1 / 24
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 stars (5) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on... View all property information
    Location Information
    Key West, Florida Keys
    1 / 12
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. Thoughtful details are luxuriously appointed to suit the vacation guest looking for privacy and high design. Walk up the brick drive and enter the gate to the palm tree lined... View all property information
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    Key West, Florida Keys
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Paradise Palms is decorated in a tropical motif, with a palm matelassé and herb-green pinstriped bed skirt. There are wood furnishings throughout, along with nautical prints and souvenirs. Double doors open onto our second story landing where you are only steps away from the upper sun deck of our... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
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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
    Location Information
    Key West, Florida Keys 33040
    1 / 18
    4.5 of 5 stars (32) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
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    1 / 24
    4.5 of 5 stars (16) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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 / 27
    2 of 5 stars (1) Poor
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Seaport Suite is available for daily or weekly vacation rentals and located on the second floor of 219 Simonton in Old Town Key West. The location is as close to perfect as you can get, being one block off Duval Street and within walking distance to every single thing you could possibly want to do.... View all property information
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    Key West, Florida Keys 33040
    1 / 32
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This nightly group rental consists of 3 separate units Porchside Paradise, Orange Blossom Suite, Deckside Suite. Three separate bedrooms with queen sized beds. Two sleeper sofas and two private hot tubs! Located at 510 Petronia St, literally steps from Duval St! Take advantage of the vivid... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    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, even your canine family members (for a small nightly fee), for a memorable tropical retreat. Situated in the premiere gated community of Truman Annex, this home is just... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 stars (38) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming 1 & 1/2 story... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Havana Oasis is comprised of two of our most popular homes! Island Oasis The beaches of the Atlantic Ocean are less than a 7 minute blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    3 of 5 stars (1) Average
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    As the name suggests, the Garden House's "Waterfall" rooms are tucked behind the tropical lagoon's waterfall... Just steps away from the breakfast and sitting area. Considering the location and price, you will not find a better deal in all of Key West This cozy bedroom shares a bathroom with... View all property information
    Location Information
    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
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Garden
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    • x
    About this property
    This 2 bedroom, 1 bath property is nestled on a quaint lane in Old Town, Key West. Not only is it 5 blocks from the beach and walking distance to the bars and restaurants, it has been recently renovated and has brand-new appliances and furniture. The location comes with a valuable (worth $500)... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Children's Pool
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    About this property
    Spacious residential-style 2-bedroom/2-bath villa features private balcony, Master suite with king bed and connecting master bathroom and spa tub; Guest queen bedroom & guest bathroom; Fully equipped kitchen with separate dining ares; Living room with sofa bed; TV/DVD Blu-Ray. Exclusive amenities... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 21
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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
    4.5 of 5 stars (39) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-styled complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... 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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    • Grill
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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 / 16
    4 of 5 stars (10) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    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 comfortable 2 bedroom unit features a huge oceanfront balcony... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    5 of 5 stars (4) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Book this property at or call our office to avoid unnecessary 3rd party service fees! Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene... View all property information
    Location Information
    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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    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 / 41
    5 of 5 stars (52) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Two Queen bedrooms upstairs (each with a private bath) and two Queen bedrooms downstairs (each with a private bath) gives sleeping privacy and convenience for up to 8. Each bedroom has flat screen TVs, air-conditioning and ceiling fan. The two upstairs bedrooms have showers, the two downstairs... View all property information
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    Key West, Florida Keys 33040
    1 / 38
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths. Enjoy breathtaking views of the... View all property information
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    Key West, Florida Keys
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome home. Literally. This secluded two bedroom home will feel like your very own! Conveniently located off of Catherine Street is your front gate to the entirely fenced in property. Enjoy a morning coffee (or mimosa) on your front porch, while the island breeze blows in your hair. When you... View all property information
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    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-style complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 24
    4 of 5 stars (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    28 DAY MINIMUM STAY IS MANDATED BY COUNTY LAW. PLEASE DO NOT SEND ENQUIRIES FOR SHORTER PERIODS!! Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush foliage, and a sparkling lagoon... View all property information
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    Key West, Florida Keys 33040
    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
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Duval Hideaway features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. Each of the queen bedrooms has a 24' LCD TV, spacious closets... View all property information
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    Key West, Florida Keys 33040
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    MINIMUM RENTAL REQUIREMENTS due to licensing restrictions; Prefer 10 day to 2 week stays; month long stays welcome; rates go down the longer you stay; deals and specials offered. Quiet end unit located in the Truman Annex. Just steps away from Fort Zachary State park/beach; two blocks from Duval... View all property information
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    Key West, Florida Keys 33040
    1 / 19
    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
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    Key West, Florida Keys 33040
    1 / 22
    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Perhaps the best value in the Curry House, Room four is simply stunning. The walls have remained unpainted, revealing the solid construction of native, Dade County pine which is naturally resistant to the adverse effects of the local environment. Room Four shares a bathroom with Room 3. The... View all property information
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    Key West, Florida Keys 33040
    1 / 38
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
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    Fantastic 1800 Atlantic Penthouse 2 bedroom 2 bath top floor ocean-view condo at 1800 Atlantic. This unit has been totally renovated and no attention to detail spared. The Master Bedroom has king bed, The guest bedroom has a queen and the living room has a queen pull-out sleeper sofa. High speed... View all property information
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    Key West, Florida Keys 33040
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Whether you want to connect or reconnect with the island paradise of Key West, this residence, aptly named The Sanctuary, is a dream destination. Its L-shaped architectural design centers around a temperature-controlled pool, built-in hydro massage spa, graceful waterfall, and outdoor rain shower.... View all property information
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    Key West, Florida Keys
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 21
    5 of 5 stars (9) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    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 / 34
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 37
    4 of 5 stars (11) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    **Recently Renovated!! Located in Duval Square (between Duval St and Simonton St) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe), This development extends from Duval Street to Simonton Street and is in the heart of historic Old Town. It is... View all property information
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    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Location, location, location!<BR><BR>Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this monthly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided.<BR><BR>This property will meet all of the... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
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    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 as few do in Key West. The breathtaking view can be seen as soon as you enter this spacious 2 bedroom condo. It has just been purchased and... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Balcony
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    • x
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    About this property
    THE HARRY SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each suite... View all property information
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    Key West, Florida Keys 33040
    1 / 52
    5 of 5 stars (14) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    Almost Southernmost Retreat is made up of Part of ALMOST SOUTHERNMOST and Part of ALMOST SOUTHERNMOST TOOon the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker... 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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    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 / 14
    4 of 5 stars (15) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040