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Holiday Rentals in Key West, FL

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    5 of 5 stars (20) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    5 of 5 stars (64) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (28) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Key West Vacation Rentals 2 Bed 2 Bath Condos On The Ocean with ocean and partial ocean views - rent weekly or nightly. To see both my condos on my website with active availability calendars and virtual tours - Scroll down to "About the owner" and in that box click on the "See more" button -... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    3 of 5 stars (5) Average
    7 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once authentic and magnificent. If you have ever had the opportunity to stroll the residential streets of the Historic Seaport of Old Town of Key West, you have... 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
    This is a House Boat that is 45 feet long and 18 feet wide two story. The Boat House is located Sunset Marina over looking the Gulf Of Mexico. Fisherman paradise and couples paradise. You are just minutes for all of Key West excitement. The marina is very quite and the water is crystal clear. You... View all property information
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    Key West, Florida Keys KEY WEST FL 33040
    1 / 16
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 / 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
    Location Information
    Key West, Florida Keys
    1 / 24
    4.5 of 5 stars (30) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • ?
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    • x
    About this property
    Everybody knows it's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. From your private and... View all property information
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    Key West, Florida Keys
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 29
    5 of 5 stars (5) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick 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.... View all property information
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    Key West, Florida Keys
    1 / 12
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
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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 / 21
    4 of 5 stars (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
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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
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Big Coppitt Key near Key West, Florida Big Coppitt Key is located just ten miles from historic Key West. This three bedroom, two bathroom waterfront home is in a pristine location and available for monthly rental of $3,250.00 from May to December 2016. Upscale furnishings. Quiet neighborhood. Dock... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    5 of 5 stars (20) Excellent
    Private Room, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • ?
    • ?
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    • x
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
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    About this property
    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 / 20
    4.5 of 5 stars (9) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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
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    1 / 32
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Washer
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    • x
    About this property
    Why stay in a cramped hotel when you can relax in a private, quiet, and peaceful 2-acre estate! We are now running an special discounted offer for the Fall of 2016 LOCATED ONLY A 15 MINUTE DRIVE FROM KEY WEST OR THE WORLD-FAMOUS BAHIA HONDA BEACH. Welcome to a 6 bedroom (2 houses) deluxe... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Internet Access
    • Balcony
    • Satellite TV
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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. Eaton Manor sits on the north side of LaBrisa and provides easy access to... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 10
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
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    • Private Garden
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    • Pet-friendly
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    • Smoking allowed
    About this property
    Beautiful home in the desirable canal front community of Key Haven. At the end of a quiet street this 3/2 home features a 2010 renovated kitchen, gorgeous enclosed back porch for relaxing, 2 boat lifts on the canal. The home is set deeply off the street for privacy, and has a long driveway for 2+... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    The "SeaJay" at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 stars (54) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. 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, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Olivia's Flower Unique architecture, a rich history, and a classic Key West neighborhood are just part of the special appeal of Olivia's Flower. This one time flower shop is now a 2 bedroom, one bath, open concept home featuring vaulted ceilings, light drenching storefront windows, a secluded... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 stars (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    Stay on our fabulous 3 bedroom houseboat and you'll have a vacation that will challenge your imagination! This spacious vacation rental on the water comfortably sleeps up to 8 guests and is completely air-conditioned and heated to keep you comfortable even on the hottest days! Your full kitchen... View all property information
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    Key West, Florida Keys 33140
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Pet-friendly
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    • x
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    • x
    About this property
    Plan your Thanksgiving getaway at this spacious residential-style 2-bedroom/2-bath villa features private balcony, Master suite with king bed and connecting master bathroom and spa tub; Guest queen bedroom & guest bathroom; Fully equipped kitchen with separate dining ares; Living room with sofa... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    En Plein Air is a property that was purchased by the owners for its heritage and natural light. An artist lives here in this former general store. Recently renovated, it remains sympathetic to its 1880s roots. All the rooms have ceiling fans and air conditioners. Modern conveniences include a new... View all property information
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    Key West, Florida Keys
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 12
    4 of 5 stars (16) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
    • ?
    • 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
    4.5 of 5 stars (69) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    SPECIAL DISCOUNTS FOR AUGUST & SEPTEMBER. INQUIRE!!! 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 equipped kitchen that looks... View all property information
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    Key West, Florida Keys 33040
    1 / 6
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    Perfect for two families wanting to vacation together or large groups. This is a large duplex home with a total of 5 bdrms and 3.5 bathrooms: One side has 3 bdrms (two rooms with queen, one room with 2 twins) + 2 baths. The other side has 2 bdrms (one room with queen, one room with 2 twins) + 1.5... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    6 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    About this property
    Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES consist of four Luxury Vacation Rentals that can be rented together or separately. LOCATED ONE HALF BLOCK FROM DUVAL STREET, this location is perfect for a multi generation family... View all property information
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    Key West, Florida Keys 33040
    1 / 7
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The Treetop Studio is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 41
    4.5 of 5 stars (46) Very good
    10 Bedrooms, 7 Bathrooms, Sleeps 20 | Quick View
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    About this property
    THIS ISN'T JUST A HOUSE, THIS IS YOUR OWN PRIVATE MINI RESORT IN KEY WEST, FLORIDA. THIS IS THE PROPERTY USED BY MTV TO FILM THE 2006 REAL WORLD KEY WEST. 500 FEET OF OCEANFRONT, 8 to 10 BEDROOMS are available (sleeps up to 20) , 5 1/2 baths, 11 plasma TVs, pool table (and Ping Pong), tennis... View all property information
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    Key West, Florida Keys 33040
    1 / 18
    4.5 of 5 stars (24) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    CALL AND ASK ABOUT OUR WEEKLY SPECIAL WITH 1 NIGHT FREE! You will love staying in this great Key West historic old town location where 90% of the residents are local. They each have an interesting Key West tale to tell and are a very warm,friendly and diverse group. Here you will absorb the... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view of the... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Spacious, tranquil Old Town Key West home. Two bedrooms, 2.5 bathrooms, sleeps up to 7. NOTE: On this page, TripAdvisor is showing our summer price. The price changes seasonally. NEW PRICE FOR APRIL. We are booking monthly renters for April, September, and November, 2016, and April, and... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    30 DAY MINIMUM Two charming Conch houses are joined together at Eliza’s Jewel, an elegant three-bedroom home in Old Town Key West. Located in a quaint neighborhood just steps from the restaurants, shops and art galleries of White Street, Eliza’s Jewel combines beautifully preserved historical... View all property information
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    Key West, Florida Keys
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    30 DAY MINIMUM RENTAL .... NO PETS ACCEPTED Break away from it all at Escape on Fleming. This comfortable and fresh two bedroom one bathroom apartment is located in the heart of Old Town. Conveniently located near charming Old Town restaurants such as Azur and Cafe Sole, yet off the beaten path,... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (11) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Truman Annex Best Location in Town!! 2 Bedroom 1 Bath ground floor Shipyard Condo. This beautiful condo sits on a private quiet walking lane and is just a 5 minute walk to downtown where you will find Key West's famous bars and shopping. Also a 10 minute walk to Ft. Zachary Taylor, our beautiful... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    30 DAY MINIMUM RENTAL: 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 elegant 2 bedroom unit features a huge... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
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    Let year-round warm breezes transport you to deep relaxation at this three-bedroom, three-bathroom Key West vacation rental. The home's great amenities include a shared pool, a gym, and plenty of space for up to six guests! This home is located on Stock Island, which is between Key West and Boca... View all property information
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    Key West, Florida Keys 33040
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    30 DAY MINIMUM RENTAL This stately home, located in the center of historic downtown Key West, offers up a perfect combination of location, charm, space and privacy. The entrance hallway and staircase are bright and airy, decorated in cool blue tones and exposed Dade county pine. The downstairs... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    30 DAY MINIMUM RENTAL Thompson's Court is the quintessential south Florida home: a sprawling, peach-colored, ranch-style design with large doors and windows that let in the natural sunshine. The large living area is decorated in charming vintage wallpaper and bright, tropical colors. To the left... View all property information
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    Key West, Florida Keys 33040
    1 / 70
    3 of 5 stars (3) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    This popular island destination is the site of the only living coral reef in the coastal regions of the US. In addition to the marine life and water activities other features of Key West include natural preserves and unique land animals. Coconut Mallory Resort and Marina is located in Key West,... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
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    This 2 bedroom, 1 and ½ bath end unit town home is located on President's walk ( Ivory Coast) in the prettiest section of the Truman Annex. The home is decorated in exceptional taste; including a King size bed in the master bedroom with ample closet space and its own private covered deck for your... View all property information
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    Key West, Florida Keys 33040
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Waterfront
    • Balcony
    • Air Conditioning
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    ATTENTION; July 5 thru Aug 28_ $214.99 - [6-7ntstay] $229.99 [4-5nt stay] For your expediency -- BASE RATES are right here in this paragraph- RATE INFO - See base rates below -over cede RATE SECTION as site has a glitch---not correct in rate section –Read our info here before calling and... View all property information
    Location Information
    Key West, Florida Keys 33040