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Vacation 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.
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    3 BedroomsSleeps 6Quick 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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Reviews
    1 BedroomSleeps 4Quick View
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    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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 BedroomsSleeps 8Quick View
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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....
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 BedroomsSleeps 6Quick View
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    • Balcony
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    About this property
    Amazing sweeping views of the Atlantic from Mojito;s in Paradise. Watch the sun rise over the Atlantic from the comfort of your King size bed in both bedrooms, access to the private balcony from both bedrooms and living room. Full kitchen. Just a stones throw from the beautiful pool and Jacuzzi....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Reviews
    3 BedroomsSleeps 8Quick View
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    • Hot Tub
    • Children's Pool
    • Waterfront
    • Ocean Views
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    Pet friendly
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    About this property
    One of the very few & one of the largest Ocean Front Suites in Key West. 2200 sq. ft living area. This place is really incredible! it's one of the largest oceanfront suites in Key West. 3 bedroom, 2 bath, 2200 square ft .You are literally 20 yards from the oceans edge. The wrap around balcony...
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    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Review
    1 BedroomSleeps 6Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    OVERVIEW The Cigar 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 four (4) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (1) queen...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Review
    2 BedroomsSleeps 4Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    For those of you who want to stay as close to Key West as possible without paying those outrageous Key West prices, stay with us between mile marker 10 and 11 in this waterfront condominium. This small, yet efficient penthouse condominium, 672 sq. ft., stands alone as a roof unit on building 3 of...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 BedroomsSleeps 6Quick View
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    Located in the heart of Key West, hidden within lush and tropical surroundings, is the breathtaking Carriage Courtyard! 3 separate cottages with 3 bedrooms and 2.5 bathrooms total, private pool, hot tub, grill, off street parking and breathtaking interi Additional amenities include: outdoor...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Reviews
    2 BedroomsSleeps 4Quick View
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    About this property
    CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have been looking for in a vacation rental home. Plenty of space, beautifully furnished...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    9 Reviews
    1 BedroomSleeps 4Quick View
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    • Grill
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    Pet friendly
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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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • Grill
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Second to none is the Big Bahama House. In this 3 bedroom home, you will enjoy private outdoor space and brand new features throughout. Downstairs, you can take in the pool and outdoor views from every window. The kitchen, has brand new appliances, plenty of counter space and bar seating. You...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 BedroomsSleeps 6Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overlooking the beautiful tropical courtyard area, This property is totally renovated and tiled throughout. Both bedrooms feature a King size bed for your comfort and a flat screen TV. The unit is colorful and tropical giving you a feel of the Islands. You are just steps away from the fabulous pool...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    30 Reviews
    2 BedroomsSleeps 4Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Review
    7 BedroomsSleeps 18Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Our unique property consists of 3 suites (a total of 7 bedrooms and 6 baths) with 2 sparkling lagoon style dipping pools in one compound in the luxurious Casa Marina area of Old Town Key West. We can accommodate groups up to 18 guests. The breakdown of the 3 suites which are being rented...
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    Key West, Florida Keys 33040
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 18
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    2 Reviews
    StudioSleeps 6Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bathrooms, Sleeps 6
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    • Waterfront
    • Satellite TV
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    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bathrooms, Sleeps 6
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    21 Reviews
    2 BedroomsSleeps 6Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    21 Reviews
    1 BedroomSleeps 2Quick View
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    • Shared Garden
    • Hot Tub
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    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Romantic, Private, Boutique Guesthouse with only 2 suites in Key West, Florida steps away from the Beach and Ocean and the Key West Wildlife Center. Reserve 1 room for a couple or both rooms to accommodate up to 4. The owners Capt. Steve and Kayla offer Snorkeling, Sunset trips, eco-adventure...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 BedroomsSleeps 6Quick View
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    Smoking allowed
    About this property
    Steps to the Beach and Sunrise Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnished with all of the comforts of home. Large flat screen tv, ensuite bath, full laundry center, fully stocked kitchen, assigned parking bay and...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Reviews
    5 BedroomsSleeps 12Quick View
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    About this property
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re craving a Key West beach accommodation with a bone fide front-line view to the sea, you know they’re not easy to come by. But in this pretty vacation rental condominium, By The Beautiful Sea, you can instantly gratify this need for sensational vistas from your own vacation rental terrace...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bathrooms, Sleeps 6
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    • Air Conditioning
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    About this property
    Nicely decorated two bedroom 1st floor condominium with an excellent location very close to the pool. This unit has an extra large floor plan with an extensive private balcony. Both bedrooms and the living room feature sliding glass doors that open on to the private balcony overlooking the lush...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Reviews
    3 BedroomsSleeps 8Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 10 days please contact us for reduced rates! Cruises can be added on for additional fee. Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    About this property
    This property is quite the hidden gem! Located on the second story of one of the most famous streets in the world, you will find Duval Dreamin'. The home over looks Duval Street and features TWO living areas, TWO bedrooms and TWO bathrooms. This is the perfect pad for couples, friends or family...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    15 Reviews
    1 BedroomSleeps 2Quick View
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    About this property
    Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a "cozy condo hideaway in the heart of historic Key West." The historic significance is close to home. It starts with the white stucco building that houses this suite and other...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pet friendly
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    About this property
    Constructed in 2001 this home has loads of Key West charm. There are two bedrooms upstairs each with their own bath and private porch. The main floor is filled with natural light and perfect for entertain with an open concept. French doors lead to the rear deck and saline pool with waterfall. Many...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    38 Reviews
    3 BedroomsSleeps 6Quick 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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    3 BedroomsSleeps 8Quick View
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    About this property
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Review
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    • Private Garden
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    About this property
    <BR> KEY WEST VACATION CONDO RENTAL DESCRIPTION<BR><BR> Our beautiful deluxe one bedroom condo in Key West Florida on<BR>Southard Street is just blocks from the ocean and Duval street.<BR>Located in historic old town, the condo is enclosed in a beautiful<BR>garden on the ground floor. It is...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
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    About this property
    Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Reviews
    1 BedroomSleeps 2Quick 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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Reviews
    2 BedroomsSleeps 5Quick View
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    • Balcony
    • Terrace
    • Air Conditioning
    • Washer
    • Secure Parking
    • Satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    49 Reviews
    1 BedroomSleeps 4Quick View
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Internet Access
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • Internet Access
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***Due to licensing restrictions, this home requires a minimum stay of 28 nights Say hello to Key West livin' at its finest. Paradise On Pearl is tucked away and offers ultimate privacy but is close enough to all of the downtown action. Come home to this newly renovated 2 bedroom, 2 bathroom...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    8 Reviews
    StudioSleeps 10Quick View
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    • Wi-Fi
    • Patio
    • Satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bathrooms, Sleeps 10
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    2 Reviews
    4 BedroomsSleeps 7Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Internet Access
    • Satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    • Satellite TV
    • Private Outdoor Pool (Unheated)
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The shell of a Nautilus provides a home for this ocean animal, making Nautilus House your home away from home. So leave your worries behind and lounge by the private pool or swing in the hammock. The 3 bedrooms and 2 bathrooms comfortably accommodates all that stay. A well stocked kitchen allows...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    47 Reviews
    StudioSleeps 2Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Internet Access
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Reviews
    2 BedroomsSleeps 6Quick View
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    • Grill
    • Washer
    • Internet Access
    • Satellite TV
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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! The Foundry is a non-smoking community within the Truman Annex. Classic and beautiful...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    47 Reviews
    1 BedroomSleeps 2Quick View
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    • Patio
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 BedroomsSleeps 6Quick View
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    • Sauna
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our paradise please enjoy our modern 1400 square foot 2 bedroom 2 bathroom totally renovated condo. This condo is one of the nicest you will find in the complex. There is music available in every room even the master bathroom. We have thought of everything there is even a flat screen tv...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    3 BedroomsSleeps 8Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Reviews
    3 BedroomsSleeps 6Quick View
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    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Waterfront
    • Hot Tub
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Children's Pool
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bathrooms, Sleeps 12
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