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Key West Cottages

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    Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.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! Downstairs is a...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Cozy Condo in Prime Location! Right off of Duval Street! Located just steps off of world famous Duval Street, Duval Canopy is the perfect blend of comfort, location and value. Just a few blocks from The Southernmost Beach, the Southernmost Point, and other favorites like The Butterfly Conservatory...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Rosie is at anchor in harbor just off the bustling downtown life of Key West. She has a very comfortable queen size V berth bed, a cozy saloon (living room) great for curling up, amazing sunset views, and in a very friendly neighborhood of boats! Rosie is a 33ft Pearson Sloop anchored only a...
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    Key West, Florida Keys 33040
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    4 of 5 bubbles
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    Fishtail Hideaway will make you feel like you may never want to return home with its intimate, private garden from all the fun and beauty Key West has to offer. Your living area offers a brand new, large, comfortable couch; which also serves as a sleeper sofa. Unique art hangings and decorative...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    4.5 of 5 bubbles
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    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! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with Caribbean colors and wood floors. Key West Vacation Rentals...
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    Key West, Florida Keys 33040
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    4.5 of 5 bubbles
    17 Reviews
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    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 of 5 bubbles
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    BAHAMA DREAMING: A beautifully renovated Conch cottage in Key West, conveniently located in the center of Old Town, one block behind celebrated Duval Street, quiet and private. Only a short walk to the many attractions, Key West activities, world-renowned Key West restaurants and nightclubs,...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4.5 of 5 bubbles
    14 Reviews
    1 Bedroom, Sleeps 4Quick View
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    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 sandwiches and homemade ice-cream at the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    About this property
    Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4.5 of 5 bubbles
    48 Reviews
    1 Bedroom, Sleeps 2Quick View
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    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 saved to create that unique historic feel...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4.5 of 5 bubbles
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    Brand New to the Rental Market! Part of Banana's Foster Guest House This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4 of 5 bubbles
    25 Reviews
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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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 of 5 bubbles
    8 Reviews
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    About this property
    Located at Papa's Hideaway an 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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    4.5 of 5 bubbles
    22 Reviews
    1 Bedroom, Sleeps 4Quick View
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    AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA! The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more! The spacious, beautifully furnished great room features a living...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    4 of 5 bubbles
    16 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    2 Reviews
    Studio, Sleeps 4Quick View
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    Part of Southernmost Sanctuary Suites The Osprey Suite - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a Queen Bed as well as a sofa for...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    4.5 of 5 bubbles
    29 Reviews
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    The Truman 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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4.5 of 5 bubbles
    8 Reviews
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    About this property
    Papa's Hideaway was 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 rustling...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Pet friendly
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    About this property
    Part of Banana's Foster Guesthouse. This cute and colorful studio is perfect for anyone who is excited to explore Key West on a budget. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at...
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    Key West, Florida Keys 33040
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    5 of 5 bubbles
    3 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach.<BR>This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Gorgeous monthly rental next to the golf course on stock island in Key West! This spacious condo is located next to the best dining and water activities the island has to offer! When you walk into the condo, you will be fall in love with the island feel of the home. The breeze hits the palm trees...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 of 5 bubbles
    5 Reviews
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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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    About this property
    This private ground floor waterfront home is located in the Key Haven subdivision of fine homes. Beautifully decorated with all new furniture, new flat screen televisions, new beds that includes two king size for extra comfort, large open living room with french doors invites in the tropical...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Stay in a beautifully restored Century Old Conch Home by the Southernmost Point, the beach and Duval Street. Enjoy the nightlife of what Key West has to offer without the need to drive or take a taxi. No detail was left undone through- out this home featuring lots of dade county pine and...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 of 5 bubbles
    1 Review
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    This cute and colorful studio is perfect for anyone who is excited to explore Key West. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at Mallory Square and a bite to eat on the harbor....
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** This 2 bed 1 bath unit is located in the quiet and desirable Truman Annex neighborhood. You will be just a short walk from both the liveliness of Duval St and the serenity of the Gulf at Ft Zachary Taylor...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 of 5 bubbles
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    About this property
    Papa's Hideaway was an 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. This studio is located on the second floor and offers a king-size bed, queen-size sleeper sofa,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    4.5 of 5 bubbles
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    2 Bedrooms, Sleeps 7Quick View
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    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,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hello prospective guests! Our great little spot is only a monthly rental but I am sure you will find our rate for a month is less expensive than most for a week. Please consider a longer stay on our island while saving some money by doing so. In a great location,nestled underneath a Spanish...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
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    ************************************************************************************************************************ NOTE: We are currently accepting only monthly rentals (28 days or longer). Please inquire for a quote....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    In one of the most desirable locations in Key West, you will find the exquisite 2CoolFish. Located in Truman Annex. Just walking into this pristine home will take your breath away. Featuring two bedrooms and one and a half bathrooms, this home is perfect for a family or small group of friends...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4.5 of 5 bubbles
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    Part of Southernmost Sanctuary Suites Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An adorable front porch to watch the people biking, walking or scooting along. Start your mornings on the porch with your Cuban coffee and a good book before...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    4 of 5 bubbles
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    2 Bedrooms, Sleeps 6Quick View
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    Tropical Hideaway - Lush gardens surround this lovingly renovated vacation home. This one-story, 2 bedroom 1 bathroom condo features a living room with queen sized pull out sleeper sofa, cable TV, DVD, stereo with CD player, and FREE wireless internet. Each bedroom has a queen sized bed and flat...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    This newly renovated, one bedroom, one bathroom unit comfortably sleeps four guests. From the moment you walk in, you will be amazed by the detail, decor and furnishings. The perfect rental home for those who wish to be just above all the action! You and your guests will enjoy the spacious...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
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    3 Bedrooms, Sleeps 6Quick View
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    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 a tub and full vanity, and an open, spacious living room with beautiful furnishings....
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    1 Review
    1 Bedroom, Sleeps 4Quick View
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    This 1 bedroom, 1 bathroom unit is right downtown and features everything you will need for your Key West getaway! Located next door to other vacation rentals such as Mary's Backyard Too and Banana's Foster Guesthouse and across the street from Seaport Suite. The location itself could not be...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4.5 of 5 bubbles
    2 Reviews
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    About this property
    Located in the middle of Duval St, you are a 15 minute walk in one direction to the Atlantic Ocean and the Southernmost Point, and the same distance to the Gulf of Mexico and Mallory Square. Shopping, nightlife and the best restaurants are outside your front door. Hemingway House is 2 blocks away!...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    • Balcony
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    About this property
    Why stay in one room in a hotel when you can have a whole home? This home has 2 bedrooms, large living room/dining room combination that opens to a deck, and it's own reserved parking space. There is a great community pool that has lots of tropical landscaping and an exercise room in the...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4.5 of 5 bubbles
    23 Reviews
    1 Bedroom, Sleeps 4Quick View
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    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 door! Abaco Suite, is a bi-level suite with a very spacious...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • Wi-Fi
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    • Washer
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, Location, Location!! Sunrise off Southard is a cozy one bedroom condo located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval St....
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Room 1 is considered by many to be one of the nicest rooms the Curry House has to offer. The recently remodeled private bathroom is spacious and includes a stunning tiled, marble shower. A semi-private veranda overlooks the pool. The veranda provides an excellent place to sit, relax & enjoy the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    • Grill
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    Pet friendly
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    About this property
    This property has a 7 night minimum due to HOA rules :) Welcome to Truman Tranquility - the perfect vacation rental for family & friends alike. The living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private patio, which features...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4.5 of 5 bubbles
    30 Reviews
    1 Bedroom, Sleeps 4Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This immaculately clean and comfortable well air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen TV and stereo. The living room has tropical furniture and a new Queen Sleeper Sofa with gel memory foam mattress. The efficiency...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Welcome to your own private sanctuary among the lush landscape of Key West - envision old-fashioned screen-enclosed porches, gardens bursting with tropical flowers and crystal...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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