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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    6 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    The Poinciana Place Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The Garden at Poinciana Place is a cozy and... View all property information
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    Key West, Florida Keys 33040
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    28 Night Minimum - Monthly Rentals Only History buffs love to immerse themselves in the centuries old legends of Key West – and if they’re lucky, they’ll find room in Smuggler’s Den to celebrate the tall tales of smugglers, pirates and colorful outlaws whose stories are part of the fabric of the... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 bubbles (55) 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 33040
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This private ground floor waterfront home is located in the Key Haven subdivision of fine homes. Beautifully decorated with all new furniture, new flat screen televisions, new beds that includes two king size for extra comfort, large open living room with french doors invites in the tropical... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 bubbles (6) 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
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    Key West, Florida Keys
    1 / 23
    5 of 5 bubbles (4) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    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 / 16
    4.5 of 5 bubbles (6) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    THE MARGARET 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... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Strikingly set in the oft-missed Key West Beachside neighborhood, we find Island Elegance ~ Near the Beach, making a seriously smart curbside statement showing a tall white privacy wall topped with shimmering green louvers. Completely renovated in summer 2012, to modern luxury standards, this... View all property information
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    Key West, Florida Keys 33040
    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 33040
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Kali Zoi House – The Good Life in Old Town Key West Kali Zoi is Greek for “good life.” That's what you'll have when you book a stay in this large, classic conch style house in historical Old Town. This 1,960 square foot, 2 story house has all of the charm of a 19th century home but was... View all property information
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    Key West, Florida Keys 33040
    1 / 18
    2 of 5 bubbles (1) Poor
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    An exclusive island style brownstone perfectly nestled in Key West's most prominent gated waterfront neighborhood known as 'Truman Annex', this striking tri-level historic building has all the architectural allure of a 19th century urban brownstone with an unparalleled modern Caribbean... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Yard
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    This 2-bedroom 2-bath cottage is located in a small compound of 8 cottages behind its own privacy fence. French doors offer access from each bedroom, living room and kitchen onto a grand private deck with ample space for entertaining or relaxing with a book. Master bedroom has a queen bed with bath... View all property information
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    Key West, Florida Keys 33040
    1 / 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Stay in a beautifully restored Century Old Conch Home by the Southernmost Point, the beach and Duval Street. Enjoy the nightlife of what Key West has to offer without the need to drive or take a taxi. No detail was left undone through- out this home featuring lots of dade county pine and... View all property information
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    Key West, Florida Keys 33040
    1 / 12
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. <BR><BR>Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    4.5 of 5 bubbles (27) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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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. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 20
    4.5 of 5 bubbles (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
    1 / 17
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    In this case... 'Two is definitely better than One'! A rare set of early 1900's 'twin-cigar maker's cottages' perched on the southern end of famous Duval Street. The Twice As Nice  vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Without a doubt, this vacation-defining residence will become as much a part of your holiday memories as the island of Key West itself. Its two-story classic Conch architecture, centrally located in Old Town, includes two spacious master bedrooms, two full en-suite baths, one half bath, a large... 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 33040
    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Hyatt Sunset Harbour Residence Club. *2016 Certificate of Excellence Winner TripAdvisor* **1 WEEK RENTAL 5/28/17 to 6/04/17**. Location, Location, Location. Private Balcony. 2 bedroom 2 bath. Full kitchen, dining table and living room includes sofa bed. Can accommodate up to six people . TV's... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    4 of 5 bubbles (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites. Opposites attract... View all property information
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    Key West, Florida Keys 33040
    1 / 45
    4.5 of 5 bubbles (2) Very good
    9 Bedrooms, 7 Bathrooms, Sleeps 22 | Quick View
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    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 / 22
    5 of 5 bubbles (20) Excellent
    Private Room, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Very private gated compound right in the heart of Key West's Old Town. Enjoy the beat of Key West's nightlife, the romance of sunset at Mallory Square, or the excitement of deep sea fishing or water sports all less than a two-minute walk from our tropical paradise. Standing outside the gate, on... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    30- Night minimum stay: Private and quiet, this luxurious unit is an ideal place for relaxing away from the noise and partygoers of Duval Street, while still being only a few minutes away from the unique charm of Old Town Key West. Beautifully decorated with palm tree décor, leather sleeper sofa,... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 bubbles (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This tropically... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    3 of 5 bubbles (1) Average
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Lovely studio apartment on the first floor of the historic Sailmaker's House. This vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. You will be living the Key West Life to it's fullest in this highly desired walking neighborhood in Old Town Key... View all property information
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    Key West, Florida Keys 33040
    1 / 33
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    If you love the residential areas of Key West then the quiet, wide streets of The Meadows of Old Town is where you want to be! The “Lemonade Mermaid” is a newly renovated historic 2 bedroom 2 1/2 bath private cottage. Off street parking in the driveway PLUS additional street parking with no... View all property information
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    Key West, Florida Keys 33040
    1 / 34
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    New owners and wide open availability! It is not too late to come to Key West! Key West Casablanca is the perfect get-a-way vacation rental for two! Key West Casablanca is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a... View all property information
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    Key West, Florida Keys 33040
    1 / 12
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Located in the Old Town Meadows neighborhood of Key West, this spacious two-story, two-bedroom historic home has access to excellent amenities and will be a highlight of your relaxing vacation to Key West. Recently renovated with luxurious furnishings, "Casa Bianca 1411" captures the peace and... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    This gulf front and canal front home has spectacular views and water access to deep water. The front yard faces the blue green gulf and the backyard gives you access to clean wide boating canal. Main living is elevated and surrounded by private balconies. Just a few minutes to Key West. Additional... View all property information
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    Key West, Florida Keys 33040
    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 33040
    1 / 20
    3 of 5 bubbles (8) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 bubbles (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 33040
    1 / 10
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • x
    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Key West, Florida Keys
    1 / 14
    5 of 5 bubbles (73) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    SPECIAL DISCOUNTS: FANTASY FEST IS ABOUT TO BEGIN OCTOBER 21-26. JOIN THE FUN!!! 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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Secure Parking
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    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    MINIMUM RENTAL REQUIREMENTS due to licensing restrictions; 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 Street and one block from The Green Parrot. Walking... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (20) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • DVD Player
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    • Private Outdoor...
    • Hot Tub
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    • Patio
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    4 of 5 bubbles (16) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Balcony
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • 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. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    4.5 of 5 bubbles (10) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Porch
    • Outdoor Dining Area
    • Satellite TV
    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Newly available! The Historic Chavez House on Margaret Street! This 3 bedroom 2 bath two story eyebrow house was Built in 1870 and is in the National Register of Historic Places. Newly renovated and very well appointed! Fine linens, gorgeous furniture, ultra comfortable mattresses, and a cool... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The house is a traditional Key West cottage that has undergone a complete renovation in 2012. The charm and historic features have been retained, while all the luxuries of today have been added. There is a master bedroom, with king bed and full bath, on the first floor. Additionally, there is a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Porch
    • Grill
    • Internet Access
    • Air Conditioning
    • Washer
    • Satellite TV
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Inn Cogneato is a newly renovated beautiful 2 bedroom 2 bath home located in one of the oldest parts of Historic Key West. Surrounded by a white picket fence, this home is perfect for a couple that plans on entertaining visiting guests or family during their stay. Beautiful wood floors... View all property information
    Location Information
    Key West, Florida Keys 33040