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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 31
    5 of 5 bubbles (2) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 27
    4 of 5 bubbles (25) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of... View all property information
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    Key West, Florida Keys 33040
    1 / 41
    4.5 of 5 bubbles (23) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Located inside the Villas known as Old Town Garden Villas With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your... View all property information
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    Key West, Florida Keys 33040
    1 / 33
    4.5 of 5 bubbles (4) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Part of Southernmost Sanctuary Suites People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the back... View all property information
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    Key West, Florida Keys 33040
    1 / 33
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    The Beach Boys on one of their many trips to Key West (they are Mojito buds with Jimmy Buffett) stayed at our vacation rental called Havana Hideaway, where they wrote the song Kokomo - according to a very reliable source at the Pink Cab Company. This vacation rental is a modern two-story, built in... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4 of 5 bubbles (1) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    This lovely accommodation, with French doors that lead to the private patio, gives you a bit more privacy at Garden House. With a comfortable queen bed and private shower (located just a few steps from our lagoon-style pool), you may find that time disappears. Many guests choose to stay in the... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    2 of 5 bubbles (1) Poor
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    ***There will be maintenance scheduled in the apartment underneath this rental starting in November 2016 and lasting throughout approximately through March 2017. Moderate noise can be expected Seaport Suite is available for daily vacation rentals and located on the second floor of an historic Key... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 24
    4.5 of 5 bubbles (16) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Part of ALMOST SOUTHERNMOST RETREAT This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St. The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features a... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Part of TROPICAL VILLAGE Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 bubbles (14) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Part of the Nightly Group PALM GARDENS Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Stroll out your door and enjoy cafe con leche and the best Cuban Sandwiches at Sandy's Cafe, pulled pork... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 bubbles (23) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (21) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    The beaches of the Atlantic Ocean are less than a 7 minute walk away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    4.5 of 5 bubbles (12) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    About this property
    Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best... View all property information
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    Key West, Florida Keys 33040
    1 / 99
    4 of 5 bubbles (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in... View all property information
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    Key West, Florida Keys 33040
    1 / 35
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
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    Key West, Florida Keys 33040
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    1 / 34
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
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    Key West, Florida Keys 33040
    1 / 6
    4 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
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    Key West, Florida Keys 33040
    1 / 52
    5 of 5 bubbles (14) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    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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    Key West, Florida Keys 33040
    1 / 20
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Affordable studio w/ private bathroom and kitchenette located in The Galleria condominium complex in the heart of "Old Town" Key West. Walking distance to Ft Zachary Taylor State Park & Beach, Blue Heaven, The Earnest Hemingway House, and much more! Free WiFi, cable TV, & daily housekeeping... View all property information
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    Key West, Florida Keys 33040
    1 / 34
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (31) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    The Monroe Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    4 of 5 bubbles (27) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top bed with light weight down comforter, the... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (15) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 bubbles (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** Granite counter tops are in the well outfitted kitchen. The bath has travertine on the floors and walls- its small but very attractive with a bath/ shower combination. This great location, together with... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 bubbles (32) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    With its rich wood flooring and triple windows, this selection is truly fit for a king. Wood and cane furnishings and metal sculpted palm lamps with intricate shell shades make the guest feel welcome and relaxed. Double nightstands and a writer's desk add to the atmosphere without compromising... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool<BR><BR>Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table... View all property information
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    Key West, Florida Keys 33040
    1 / 36
    3.5 of 5 bubbles (3) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ***Both bathrooms and kitchen completely renovated as of September, 2015*** Part of Southern Palms COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 bubbles (49) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage. Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (48) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Part of the Nightly Group PALM GARDENS Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details. Osprey's Nest is an upstairs spacious unit at 905 White Street. The original Dade County pine walls have been... View all property information
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    Key West, Florida Keys 33040
    1 / 37
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    4 of 5 bubbles (8) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    Located at Papa's Hideaway is a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval Street. The perfect mix of location, atmosphere and value. Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds... View all property information
    Location Information
    Key West, Florida Keys
    1 / 27
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights***<BR><BR>MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS<BR><BR>Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    5 of 5 bubbles (3) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
    • Smoking allowed
    • x
    About this property
    Part of Southernmost Sanctuary Suites The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need... View all property information
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    Key West, Florida Keys 33040
    1 / 36
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located overlooking the tropical courtyard and garden area. Nicely decorated two bedroom two bath unit. Newly renovated bathrooms. Master bathroom has a tub and walk in shower. There is a queen in the master bedroom, two twins in the guest bedroom and a queen sleeper sofa in the living room. Both... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    4 of 5 bubbles (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    New King-sized bed w/ pillow top mattress installed June 2015 Outside the front of the complex are the tennis courts. If you choose to stay inside the complex you can enjoy the lush landscape on the inside of the courtyard. Just a short stroll takes you to the relaxing hot tub and then to the... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    About this property
    Room 6 is conveniently located on the main floor. It has a door that opens onto the side deck with a secluded sitting area. The front porch sitting area is only a few steps away. People that stay in Room six often comment on how pleasant it is to wake up to the smell of breakfast cooking nearby in... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Balcony
    • Satellite TV
    • Terrace
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    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    (Recently updated!) Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    5 of 5 bubbles (25) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
    • Patio
    • Air Conditioning
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    • DVD Player
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (4) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Welcome to Artist House: a 2 bedroom 2.5 bath rooftop townhome located within the gated community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located so that you can park your car in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 bubbles (21) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Terrace
    • Air Conditioning
    • Balcony
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    • Shared Outdoor Pool...
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Short walk to Fort Zachary State Park and South Beach! This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
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    • Internet Access
    • Grill
    • Terrace
    • Air Conditioning
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Part of TROPICAL VILLAGE Tropical Village Retreat - Lush gardens surround this lovingly restored two-story vacation house. This upstairs suite has two bedrooms each featuring a queen bed. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ grill in a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Terrace
    • Balcony
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 bubbles (27) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    • Terrace
    • Balcony
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and... View all property information
    Location Information
    Key West, Florida Keys 33040