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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 rental today, and have the perfect trip.
    1 / 15
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 47
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 20 | Quick View
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    1 / 38
    4 of 5 bubbles (16) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** a passport tucked away off of mile marker 15. While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Around the back of the... View all property information
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    Key West, Florida Keys
    1 / 53
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    4.5 of 5 bubbles (9) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention 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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    About this property
    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
    Location Information
    Key West, Florida Keys 33040
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    1 / 31
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • DVD Player
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    Looking for that unique, one-of-a-kind vacation rental that fits all your accommodation needs? Check out Lucy, our beautiful 42 ft. catamaran docked in Stock Island Marina Village. Just a short drive from downtown Key West, she's the perfect alternative to a hotel room! Bright, airy and spacious,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    4.5 of 5 bubbles (40) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Great, popular, quiet townhouse in the well-liked Duval Square complex in the heart of Old Town. One off-street parking space per unit. Easy walking distance to all downtown attractions. Bank, convenience store, health club, hair salon and fine restaurants in the complex. Families are... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (17) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The M/V Coconuts is a completely unique home with 360 degree water views. It also happens to be an exceedingly rare 50-foot Florida Bay Coaster Trawler permanently docked at the Key West Harbour Yacht Club, featuring a restaurant, infinity pool and a private beach! This is more than a boat. It... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    4 of 5 bubbles (22) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's brick, tree lined courtyard that includes shops and restaurants. These units offer well equipped kitchens and living rooms that open to a patio, or porch, two bedrooms and two baths. There is a shared... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
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    • Balcony
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    • x
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    • x
    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 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 / 25
    4.5 of 5 bubbles (7) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get that sense that you’ve been there before? When I first visited this vacation rental house, it happened to me. My mind sparked, the place seemed wonderfully familiar, and I felt an... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Save 3% off final rate if you pay by check. To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially... 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
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (24) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Porch
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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
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    1 / 35
    5 of 5 bubbles (6) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    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 hideaway is just moments away from Duval Street and the most exciting spots the southernmost... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • 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
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    5 of 5 bubbles (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
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    Key West, Florida Keys 33040
    1 / 38
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Hot Tub
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    • x
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Shark Key Chateau is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. Shark Key Chateau is... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    4.5 of 5 bubbles (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Pineapple Cottage is a two bedroom, two bathroom home with a private pool in Old Town Key West. There is total privacy and charm throughout this island home and the proximity to all things Key West is unbeatable (one block from Duval Street). Behind an enclosed, white wooden gate there is tropical... View all property information
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    Key West, Florida Keys 33040
    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Garden
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    • x
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    • x
    About this property
    Garden Oasis is a first floor condo in the Shipyard Condos in Truman Annex. We are ideally located 2 blocks from the action (restaurants, shops, clubs) of Duval St., and very short walks to sunsets at Mallory Sq, and the beaches of Ft. Zachary Tayler Park. The Shipyard is a lushly landscaped... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 bubbles (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one... View all property information
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    Key West, Florida Keys 33040
    1 / 34
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area... View all property information
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    Key West, Florida Keys 33040
    1 / 49
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    2 Bedroom 2 bath Island View King in the master bedroom, king in the the guest bedroom and a queen sleeper sofa in the living room. Plush new leather living room furniture with a queen sleeper sofa for your extra guests. 1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to... View all property information
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    Key West, Florida Keys 33040
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Hot Tub
    • Children's Pool
    • Waterfront
    • Ocean Views
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    • Pet-friendly
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    • x
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    • x
    About this property
    I rent starting the first of the month till the end of the month, or longer. Once you pay the monthly rate, you have the option of using the property for as many, or as few days as you would like during that calendar month. You have total flexibility with your arrival dates and departure dates, as... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    3.5 of 5 bubbles (9) Average
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    "In-the-know" travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    About this property
    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    About this property
    While relaxing in the free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Upon entering the 3200+ square foot home, the spacious nature of the home is evident providing ample room for large groups. Around the back of the home, the large deck with... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    4.5 of 5 bubbles (38) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | 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
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    Key West, Florida Keys 33040
    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    President’s Walk is perfectly located in the Truman Annex. A quick stroll to Duval Street and minutes from Fort Zachary Taylor State Park and its beach, this gated community offers lush gardens and a beautiful community pool at your doorstep. For Key West history buffs, Truman's Little White House... View all property information
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    Key West, Florida Keys
    1 / 16
    4 of 5 bubbles (10) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    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 / 12
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
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    About this property
    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys... 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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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    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 / 21
    4 of 5 bubbles (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    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 / 29
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This genuine Key West combo of our Private Pool Garden Villa plus a classy private studio cottage that adjoins the property next door, can be your very own get-away for a week or more. When rented together, we call the property the Lazy Iguana, and it's available to rent together from May 2016... View all property information
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    Key West, Florida Keys 33040
    1 / 19
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Hot Tub
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is... 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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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** 2 Bedrooms with king size beds, 2 Bathrooms, and a third guest room/office/ with gym equipment. Charming 2 story conch house on a quiet street in Old Town, right between Duval and Higgs Beach! Easy access to... View all property information
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    Key West, Florida Keys 33040
    1 / 58
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Sauna
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    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    1st floor garden-view unit, King in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room. This unit has high speed wireless and will accommodate up to 6 people. Just a short walk to the pool and Jacuzzi. For the Sports enthusiast there are 3 lighted Tennis... 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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    • ?
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    • x
    About this property
    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 / 14
    4.5 of 5 bubbles (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    5 of 5 bubbles (1) Excellent
    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 / 14
    2 Bedrooms, 5 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
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    • Porch
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    MONTHLY RENTAL ONLY <BR><BR>Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4 of 5 bubbles (20) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Terrace
    • Internet Access
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
    • 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. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4 of 5 bubbles (19) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Satellite TV
    • Balcony
    • Internet Access
    • Shared Outdoor Pool...
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • 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. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040