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Key West House Rentals

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    5 of 5 stars (9) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    4.5 of 5 stars (36) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shopping. Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval & South Streets). The house can comfortably... View all property information
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    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. Outdoor grill on deck. Please note that I have a licensed real estate broker in Key West who... View all property information
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    4.5 of 5 stars (6) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    Part of ALMOST SOUTHERNMOST RETREAT Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of... View all property information
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    1 / 11
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    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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    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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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... View all property information
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    5 of 5 stars (3) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 7
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    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    About this property
    Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your... View all property information
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    1 / 25
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    ***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... View all property information
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    5 of 5 stars (14) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 16
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    About this property
    Almost Southernmost Retreat is made up of Part of ALMOST SOUTHERNMOST and Part of ALMOST SOUTHERNMOST TOOon the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker... View all property information
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    4.5 of 5 stars (13) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Located at Papa's Hideaway , the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best... View all property information
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    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • x
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    • x
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    About this property
    Private Luxury Home surrounded by lush tropical landscaping. The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district of Key West. Walking distance to all Old Town has to offer, as well as a... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    Part of Conch Republic Cottages 'Porchside Paradise' is located in the front section of the 'Conch Republic Cottages'. This beautiful 'home away from home' features an inviting and spacious front porch - great for people watching - as well as a private two person hot tub. The unit is gated off... View all property information
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    4.5 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    1 / 23
    4 of 5 stars (2) Very good
    6 Bedrooms / 6 Bathrooms / Sleeps 16
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    • x
    • x
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    • Elder access
    • x
    About this property
    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual... View all property information
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    1 / 14
    5 of 5 stars (8) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    • x
    About this property
    THIS PROPERTY IS A MONTHLY ONLY RENTAL Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining, you are steps away from... View all property information
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    1 / 19
    4 of 5 stars (42) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
    • x
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    About this property
    Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West. Hidden behind the most photographed 'prohibition fence' in Key West, this three bedroom, two bathroom home includes a large sunny pool and patio as well as off street parking (1... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 6
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Nestled in tropical, flowering gardens, the Providence Suite is perfectly located, 1/2 block from Duval Street Downstairs is the living room with Queen sleeper sofa, dining room and fully equipped... View all property information
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    1 / 46
    5 of 5 stars (1) Excellent
    5 Bedrooms / 7 Bathrooms / Sleeps 20
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    • x
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    About this property
    The location is set on Center Street, which is located ½ block off Duval Street. These Villas are a favorite of our guests who like to relax in the quiet, beautiful garden area. Your party can book 1 to 5 of these Villas for a relaxing vacation. Old Town Garden Villas is comprised of the... View all property information
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    5 of 5 stars (35) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Pets allowed
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    • x
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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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    4.5 of 5 stars (4) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • x
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors,... View all property information
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    4 of 5 stars (2) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • x
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    About this property
    SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Main House is a (2) story 100+ year old, recently completely renovated Conch house. The design of this property lends itself perfectly to small gatherings of families and friends. The house can comfortably accommodate a maximum of eight (8) guests - (1)... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Absolutely Paradise! That's what you will think the moment that you arrive at this luxurious, tropical retreat. Located in the heart of Old Town Key West, this beautiful home will entice, entertain, and excite even the most discriminating traveler. This spacious (almost 2000 sq ft) three story, 3... View all property information
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    4.5 of 5 stars (12) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Waterfront
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    • Pets allowed
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    • Suitable for children
    • x
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    • ?
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    About this property
    Come stay aboard our FABULOUS houseboat Libra! Docked in one of Key West's most exclusive yacht club marinas, our guests have free access to a host of 'members only' amenities including a swimming pool, private beach, tiki bar, fitness facility, sauna, clubhouse, onsite restaurant, free parking and... View all property information
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    5 of 5 stars (15) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Suitable for children
    • ?
    • x
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    • x
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    About this property
    Very private gated compound right in the heart of Key West's Old Town. Enjoy the beat of Key West's nightlife, the romance of sunset at Mallory Square, or the excitement of deep sea fishing or water sports all less than a two-minute walk from our tropical paradise. Standing outside the gate, on... View all property information
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    4.5 of 5 stars (39) Very good
    10 Bedrooms / 6 Bathrooms / Sleeps 20
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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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    5 of 5 stars (4) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 7
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    • x
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    • x
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    About this property
    Chick-A-Pea’s Cottage: Located in the gallery district of Key West. The house is steps off of Duval St. near Hemmingway’s house, the Southernmost Point, the Butterfly Museum and great shops, restaurants and bars . The location is quiet & private… yet in the heart of key west The house is a... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Duval Hideaway features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. Each of the queen bedrooms has a 24' LCD TV, spacious closets... View all property information
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    4.5 of 5 stars (3) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    28 NIGHT MINIMUM STAY REQUIREMENT - SOUTH STREET SERENITY Beautiful Vacation Home just steps from the Beach! This light and airy 3 bedroom, 2.5 bath home has a wraparound Bahamian Style deck and expansive French doors that lead from every ground floor room to an outdoor space. Enter the private... View all property information
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    1 / 38
    5 of 5 stars (34) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 4
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    • Pets allowed
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    • x
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    About this property
    Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga... View all property information
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    5 of 5 stars (20) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    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... View all property information
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    4.5 of 5 stars (12) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Water Views
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    • x
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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 a 50-foot trawler, permanently docked at the Key West Harbor Marina. This is more than a boat. It really is a very comfortable home, with proper living area, bedrooms and large sundecks. There is over... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 10
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Cayo Hueso: As you approach the front door to 1120 Curry Lane the transformation starts to happen. The small lush tropical lane, the two wonderfully inviting porches... your journey to the tropics and... View all property information
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    5 of 5 stars (10) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • x
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    About this property
    You'll know you've found island heaven--the term heaven meaning transcendence or going beyond the ordinary--when you enter Casa Camilla. This two-bedroom, two-bathroom home located in the lovely Meadows neighborhood of Old Key West is extraordinary inside and out. The outside rear half of the... View all property information
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    4.5 of 5 stars (5) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Water Views
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    • Suitable for children
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    This is for the guest that would like to experience the yachting lifestyle without ever leaving the dock. Staying at the dock allows you to come and go as you please whether it be scootering around town or shopping, eating and drinking your way down the famous Duval St. You may just want to stay... View all property information
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    5 of 5 stars (3) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 6
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    • x
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    The Bonaire Suite is a bi-level suite decorated in a rich contemporary Palm Tree motif with two queen beds separated by a privacy curtain in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door. Downstairs is a living room with sofa which converts to a... View all property information
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    4 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • x
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    • x
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    About this property
    There's no better way to experience 'Island Time'-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with... View all property information
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    4 of 5 stars (6) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • x
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    About this property
    Resort style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amidst lush tropical landscaping, sits Island Style, the sister cottage of Hidden Treasure. One of our most popular properties, it was renovated by two fabulously funky sisters who share... View all property information
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 6 Bathrooms / Sleeps 7
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    • Safe
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    • x
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    • x
    About this property
    NEWLY LISTED WITH AVAILABILITY IN JANUARY FEBRUARY AND MARCH!!! Key West Vacation Rental 'SECRET VILLA II' A Hidden Jewel in Historic Old Town Key West Our property 'SECRET VILLA' is so popular and in such high demand, the owner has purchased and remodeled the mirror image of it to create... View all property information
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    5 of 5 stars (5) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two... View all property information
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    4 of 5 stars (9) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    If any residence deserves the location-location-location mantra, it's this two-bedroom, two-bath townhouse in Truman Annex. The first 'location' is the island of Key West, a world-class vacation destination. The second is Truman Annex, a premiere gated waterfront community named for President Harry... View all property information
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    5 Bedrooms / 5 Bathrooms / Sleeps 14
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    ***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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    5 of 5 stars (6) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Relax in paradise amongst all the comforts of home in the Sailor House, a proud member of Andrews Inn & Garden Cottages. Just a half a block off the world famous Duval Street, the Sailor House offers the ultimate in privacy and luxurious island living. Families and couples traveling together rave... View all property information
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    5 of 5 stars (21) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
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    4.5 of 5 stars (9) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Pets allowed
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    • x
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    • x
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    About this property
    The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located... View all property information
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    4.5 of 5 stars (20) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the exclusive use of compound residents. La Prive has... View all property information
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    Studio / 1 Bathroom / Sleeps 2
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    About this property
    Part of Banana's Foster Guest House This comfortable 2nd floor studio right on the corner of Caroline and Simonton, just a block off Duval, is a great spot for 2 guests wanting to be in the thick of things! After entering the compound from the shared off street parking into the courtyard with... View all property information
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