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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 12
    4 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 34
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 18
    4 of 5 stars (13) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in... View all property information
    Location Information
    Key West, Florida Keys
    1 / 28
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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
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    Key West, Florida Keys
    1 / 23
    3 of 5 stars (1) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Originally built in 1938, Amanda's Dream Suites vacation rental is a charming large wooden home offering two full stories with deep porches which overlook the garden and pool. An exterior stair case on one end of the building join the first and second floor. A renovation of the home in the early... View all property information
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    Key West, Florida Keys
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. Our condos' at La Brisa are two bedrooms with two full bathrooms on the third floor. The master bedroom has a king size bed with a walk... View all property information
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    Key West, Florida Keys
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    2 Bedroom 2 bathroom high ceilings spacious unit in Truman Annex. Bright and Airy floor plan with cathedral ceilings, balcony. Highly desirable and rare 2 bedroom, 2 bath unit. One assigned parking space, large community pool and short distance to Fort Taylor Beach. Short walk to Duval Street,... View all property information
    Location Information
    Key West, Florida Keys
    1 / 29
    5 of 5 stars (17) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Outdoor Dining Area
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    Beautiful Poolside Townhome - Perfect for family or Travel with Friends! The Best of Everything! 'Island Days' has it all: Large heated resort style pool with Tiki Hut right outside your French doors. Lush landscaping and off street parking steps to your door complete the resort feel all in a... View all property information
    Location Information
    Key West, Florida Keys
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    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
    1 / 17
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 17
    5 of 5 stars (20) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Plan your Fall getaway! Visit now through DECEMBER 15th 2016 and get a 15% DISCOUNT. Please see our Specials page for all terms and conditions. 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... View all property information
    Location Information
    Key West, Florida Keys
    1 / 29
    5 of 5 stars (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our... View all property information
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    Key West, Florida Keys
    1 / 18
    5 of 5 stars (6) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Key West, Florida Keys
    1 / 18
    2 of 5 stars (1) Poor
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    An exclusive island style brownstone perfectly nestled in Key West's most prominent gated waterfront neighborhood known as 'Truman Annex', this striking tri-level historic building has all the architectural allure of a 19th century urban brownstone with an unparalleled modern Caribbean... View all property information
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    Key West, Florida Keys
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. <BR><BR>Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and... View all property information
    Location Information
    Key West, Florida Keys
    1 / 10
    2.5 of 5 stars (3) Poor
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Perched just above the fun and frolic of Duval Street at the City Island View vacation rental suite, you're sure to capture the 'island beat' that stirs this tiny tropical island of Key West, Florida. This extraordinary Key West vacation rental features the original 2nd floor front porch that spans... View all property information
    Location Information
    Key West, Florida Keys
    1 / 30
    4 of 5 stars (39) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
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    Key West, Florida Keys
    1 / 50
    3.5 of 5 stars (2) Average
    11 Bedrooms, 11 Bathrooms, Sleeps 24 | Quick View
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    About this property
    The Meeting Point – Key West is by-far the most spacious and classically elegant vacation rental property on the island. Situated in the heart of Old Town, there is nothing else like it. If you’re looking for luxury and plenty of room, The Meeting Point is the grandest vacation rental in Key West,... View all property information
    Location Information
    Key West, Florida Keys
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    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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
    1 / 22
    4.5 of 5 stars (6) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Plan your Fall getaway! Visit now through OCTOBER 19th 2016 and get a 10% DISCOUNT. Please see our Specials page for all terms and conditions. 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... View all property information
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    Key West, Florida Keys
    1 / 20
    3 of 5 stars (8) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Key West, Florida Keys
    1 / 31
    4 of 5 stars (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.... View all property information
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    Key West, Florida Keys
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flair. Full kitchen with all... View all property information
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    Key West, Florida Keys
    1 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This 2 bedroom, 1 bath property is nestled on a quaint lane in Old Town, Key West. Not only is it 5 blocks from the beach and walking distance to the bars and restaurants, it has been recently renovated and has brand-new appliances and furniture. The location comes with a valuable (worth $500)... View all property information
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    Key West, Florida Keys
    1 / 25
    4.5 of 5 stars (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    New owners invite you to enjoy this vacation rental aptly named 'Seas the Day!' This newly updated 2 bedroom 1 bath first floor condo is located in the Shipyard section of the Truman Annex. If you are looking for a great location central to all that Key West has to offer, look no further! Park... View all property information
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    Key West, Florida Keys
    1 / 23
    4 of 5 stars (37) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    There's no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens leads to a... View all property information
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    Key West, Florida Keys
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    Key West, Florida Keys
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    MARCH STILL OPEN! 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... View all property information
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    Key West, Florida Keys
    1 / 38
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths. Enjoy breathtaking views of the... View all property information
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    Key West, Florida Keys
    1 / 25
    4.5 of 5 stars (6) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The Bella Vita is a 1 Bedroom, 1 bath, luxurious, steps from Duval Street. Bella Vita is the sister unit to the La Dolce Vita in the same building, listing 431504. Please check out our for availability, photos and video. Everything is brand new from floor ceilings! 14... 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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    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
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    Key West, Florida Keys
    1 / 9
    3.5 of 5 stars (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Key West cottage architecture has been thoroughly 'time-tested' in 'island life and culture' in this somewhat infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.' Since its original construction in the early 1900's this note-worthy Cockadoodle... View all property information
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    Key West, Florida Keys
    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Century old, two story charmer. Newly renovated throughout with elegant, high end finishes. OFF-STREET PARKING. Breezy, covered front porch and spacious fenced backyard with hot tub. Very desirable location near historic Key West Cemetery on White Street. 3 bedroom, 2.5 bath home with the perfect... View all property information
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    Key West, Florida Keys
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities... View all property information
    Location Information
    Key West, Florida Keys
    1 / 21
    5 of 5 stars (9) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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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
    Location Information
    Key West, Florida Keys
    1 / 29
    4.5 of 5 stars (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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
    1 / 25
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Plan your Fall getaway! Visit now through NOVEMBER 30th 2016 and get a 10% DISCOUNT. Please see our Specials page for all terms and conditions. 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... View all property information
    Location Information
    Key West, Florida Keys
    1 / 24
    5 of 5 stars (16) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Key West, Florida Keys
    1 / 22
    5 of 5 stars (20) Excellent
    Private Room, 3 Bathrooms, Sleeps 8 | Quick View
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    1 / 24
    4.5 of 5 stars (31) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Satellite TV
    • DVD Player
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    • Terrace
    • Washer
    • Parking
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    Location Information
    Key West, Florida Keys
    1 / 10
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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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
    1 / 31
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Balcony
    • Waterfront
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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
    1 / 21
    4.5 of 5 stars (26) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Shared Outdoor Pool...
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    • Terrace
    • Balcony
    • Air Conditioning
    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
    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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    • Balcony
    • Terrace
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    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • 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
    1 / 17
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    1 / 16
    4.5 of 5 stars (54) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Balcony
    • DVD Player
    • Internet Access
    • Satellite TV
    • Terrace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • 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
    1 / 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Stay in a beautifully restored Century Old Conch Home by the Southernmost Point, the beach and Duval Street. Enjoy the nightlife of what Key West has to offer without the need to drive or take a taxi. No detail was left undone through- out this home featuring lots of dade county pine and... View all property information
    Location Information
    Key West, Florida Keys