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Sugarloaf Key Vacation Rentals

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    Travelers to Sugarloaf Key are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    All 207 Rentals in Sugarloaf Key
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    Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok1 / 28
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Family friendly condo w/ shared pool, hot tub, & complimentary shuttle! Dogs ok!1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Dog-friendly home w/ private pool - walk to the beach and restaurants!1 / 26
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 28, 2018
    Had a great surprise birthday weekend in Key West. The house was fantastic! Very clean and bigger than the pictures make it seem. Loved the heated pool, and close walk to Duval...
    Reviewed January 23, 2017
    3 levels of beautifully decorated accommodations! Walking distance to famous Duval St, bars, restaurants and shopping. Loved it!
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    About this property
    Escape to the Florida Keys for a relaxing vacation in this three-bedroom, two-and-a-half bath home for eight (six comfortably) with a private pool and walking distance to the beach and Duval Street. And your favorite canine friend is also welcome for a small nightly fee. This rental is mere blocks...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Comfortable condo w/ shared pool, private balcony, and beach access1 / 26
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 9, 2015
    This was not as I expected. The place is very clean. Here are my things that I as not expecting. U can not go right to the beach in front of this place all rocks. Smothers beach...
    Reviewed November 16, 2014
    The condo was a very nice rental on the south side of Key West. The decor was modern and the condo had a classy feel. The large balcony patio was wonderful to sit out on in the...
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    About this property
    Escape to Key West's beaches during a stay at Atlantic Ocean View, where you'll enjoy prime island location and access to a shared pool. This condo accommodates up to six, so it's a great choice for the whole family! The condo backs up to a stretch of Higgs Beach, so you're never far from the...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dog-friendly, tropical escape with central location, hot tub, and shared pool1 / 25
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 26, 2016
    My boyfriend and I stayed here for 4 nights in October. The house was very clean and the check in process was very easy. The house has a small shared pool with the other condos...
    Reviewed July 31, 2014
    The Flamingo Hideaway is a ground floor unit in a small condo complex of renovated, period buildings. This unit is tucked away from the street and right next to the shared pool...
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    About this property
    Surround yourself with peace, tranquility, and seaside fun when you book your trip to this Key West cottage. Enjoy the bubbling hot tub, shared pool, and easy beach access. Nestled in the Palm Gardens condo community in Old Town Key West, this tropical home embraces you with island vibes and a...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!1 / 25
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 27, 2017
    My friends and I have traveled to Key West for the past three years and we always rent through KWVR. Each year we have rented a different property however this property is...
    Reviewed August 18, 2016
    Stayed here with friends. The setup was perfect for our needs - one couple and two singles. My bed was very comfortable. The only thing missing in my room was a mirror! The...
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    About this property
    Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, private pool, furnished patio, and off-street parking for two...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Dog-friendly, colorful cottages w/ pool & hot tub in a fabulous location!1 / 47
    (14)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 1, 2015
    Three generations, nine people, stayed here over Christmas. We each had space to be by ourselves, and we all had space to get together. Nine of us sat around the table in the...
    Reviewed September 3, 2014
    I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
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    About this property
    A large group getaway to Key West starts with this pair of charming cottages, which feature a total five bedrooms, three-and-a-half bathrooms, and a max occupancy of 16. The property also includes a private heated swimming pool, a private hot tub, and dog-friendly accommodations. The cottages sit...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your Key West vacation in style here at this high-end house with a private hot tub! There's plenty of room for everybody in this house's eight bedrooms, and you're steps away from the ocean. Key West's most popular attractions surround this home - walk down to Mallory Square a few blocks...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take your romantic getaway at this bright studio condo in the heart of Key West's historic Old Town! Free WiFi, a deck, and a kitchenette will have you feeling right at home less than a mile from the beach. Visit Fort Zachary Taylor State Park & Beach, about a mile away, where you'll find white...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Dog-friendly home in a quiet neighborhood w/ shared pool & private hot tub!1 / 26
    (7)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2016
    We rented the entire complex for our wedding. While my husband and I did not stay in this particular cottage we did see the interior and this was used as my "bridal...
    Reviewed May 21, 2015
    We booked this rental through Flipkey. The pictures didn't really show how nice it is. It's not the Ritz, as the other review says, but really very nice. Good kitchen with...
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    About this property
    Treat your group to a tropical getaway at this dog-friendly Key West retreat. Featuring room for up to six guests and a cute canine companion (for a small nightly fee), street parking, a private hot tub, and a shared pool, your vacation promises to be one to remember. This home is nestled in a...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the tropical surroundings of Key West in style from the comfort of this dog-friendly condo! A shared pool, ocean views, and more await you. Nestled on the northern side of Key West, you have easy access to the shops and restaurants of Old Town, as well as a dock and the fresh ocean air of...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Key West and unwind with this comfortable and inviting two-bedroom condo! A shared pool and a private balcony with scenic views of the marsh add to the feeling of relaxation. The family dog is also welcome to join you for an additional nightly fee. This colorful rental is part of the...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Four condos w/ entertainment, private parking & beach nearby - great for groups!1 / 24
    (2)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Balcony
    • Air Conditioning
    • Patio
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2014
    Lovely we'll maintained, self catering, semi-detached apartments which allows privacy yet accommodates large extended family barbecues and mingling. We hired 3 of the apartments...
    Reviewed July 28, 2014
    Pictures online are great and the property was perfect for 3 families traveling together. We tried not to be in rooms during the day since we were busy with excursions but the...
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    About this property
    Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificing privacy? This complex of four condos is your ticket - featuring entertainment, private parking, and beach access nearby, you'll have everything you could hope for on a tropical...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Patio
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
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    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the ideal spot for your next large group getaway, then look no further than this grouping of three separate Key West condos. Boasting a shared heated pool and hot tub, and space for up to 12 guests, this home makes it easy for everyone to enjoy all of the local attractions....
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Searching for an affordable long-term vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Tune into the Windchime! This lovely studio for two comes with all the comforts you need for an extended stay away from home, along with a...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wake up every morning to the crisp smell of the ocean when you stay at this cute condo on the shores of Key West! Complete with upscale resort amenities like a shared pool and hot tub, tennis courts, and a private, covered parking space, this comfortable rental is sure to become your new favorite...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key West condo! A community pool and hot tub, tennis courts, a parking space, and pool views from your private balcony add to an atmosphere of luxury and total relaxation. This...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful condo with a deck/patio & shared pool - walk to beaches, Duval & more!1 / 23
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 12, 2015
    We visited the Annex for Fantasy Fest a few years back. The location is perfect! Close enough to the action of the main streets, but private enough for some peace when you're...
    Reviewed January 19, 2015
    Great location; we loved having the back gate for direct access out to Angela Street and the close proximity to the Green Parrot and Blue Heaven - two of our Key West favorites...
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    About this property
    Find the best of Key West at your doorstep with this beautiful two-bedroom condo, a lovely South Florida escape with a private deck and patio, a shared swimming pool, and a wonderful location close to restaurants, beaches, and more! Perfectly located between Truman Annex and Bahama Village, this...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Restored historic home w/ private pool & reserved off-street parking - Dogs OK!1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 21, 2017
    My family and 2 of our friends joined us on this trip. The property was clean and close to absolutely everything. We could not have asked for a better place to stay.
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    About this property
    Start planning your Key West vacation when you book this three-bedroom, two-bathroom home. Up to eight guests will spend their vacation days lounging by the private pool, strolling the streets of downtown, and soaking up the Florida sun on soft sand beaches. The family dog is also welcome to join...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunny condo w/ entertainment, balcony, & great location near the beach! Dogs OK!1 / 26
    (1)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the land of sea and sun for your next vacation with this fresh condo in Key West. Featuring one bedroom and one bathroom, entertainment, and an awesome location close to all the action on the waterfront, up to four guests will love it here! The family dog is also welcome to join you for...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in the laid-back ambience of the Florida Keys with a stay at this colorful Key West condo! Complete with a shared pool and hot tub, tennis courts, dog-friendly policies, and a reserved parking spot, this comfortable vacation rental will have you relaxed in no time. This...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Historic house w/ private pool & easy beach access - ideal for groups! Dogs OK!1 / 31
    (1)Very good
    7 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 26, 2016
    We stayed in one of the units at the property (Banana Split). This is a 1 bedroom / 1 bath apartment on the second floor. It has a full kitchen, small sitting area and two decks...
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    About this property
    Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large historic house on Key West. Featuring a private heated pool, four private parking spaces, and a communal area with plenty of room for everyone, this seven-bedroom, eight-and-a-half bathroom house...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 7 Bedrooms, 9 Bathrooms, Sleeps 18
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    Peaceful, dog-friendly home in a residential neighborhood w/ a shared pool1 / 26
    (3)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.I did not stay in this particular cottage but our guests had rave...
    Reviewed October 7, 2014
    The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15...
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    About this property
    Treat the whole family to a seaside adventure when you book your getaway to this dog-friendly Key West cottage. Boasting a prime location close to beach activities and attractions, as well as a shared pool, this home welcomes up to six guests and a canine companion (for a small nightly fee). This...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caribbean comforts await at this lovely Key West condo just five miles from the island's historic downtown. With amenities like a private pool and hot tub, tennis courts, a private balcony, and a covered parking spot, this comfortable condo is perfect for anyone who plans to explore the island by...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cheery beach getaway near local attractions, w/shared pool & easy beach access1 / 56
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 18, 2014
    Highly recommend this facility to anyone who is looking for a conveniently located, quiet, easily acessable 2 bedroom / 2 bath condo. Our week stay was everything we could...
    Reviewed May 12, 2014
    Three friends that I have known since first grade and I traveled to Key West for a week to celebrate the year we all turn 60. Stayed at Shipyard Perch. it was perfect. The 2...
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    About this property
    Treat yourself to a stress-free vacation filled with sun-soaked days when you book your trip to this Key West condo. With room for up to four guests to a shared pool and beach lifestyle, this home will make it easy to slip into vacation mode! Located in the Truman Annex, a quick five minute walk...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    • Internet Access
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your large group of up to 18 to Key West and stay in this spectacular five-bedroom, three-bath oceanfront home for an unforgettable Florida vacation. Amenities include a private pool, massive deck with seating, lush surrounding gardens, and two private docks, as well as ready access to the...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 18
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Give your family and friends the trip to the Florida Keys they deserve thanks to this condo in Key West! A great location, along with amenities like a shared pool and private parking, ensure everyone can enjoy themselves. A dog is even welcome for a small nightly fee. Courtesy Shuttle available to...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Patio
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated on the second floor of a historic home, this spacious dog-friendly condo welcomes guests with great amenities and a private hot tub! Soak after a long day in the sunshine, and fire up the gas grill to make full use of the back patio space. You're right around the corner from Duval...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Balcony
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best of the Keys during a stay in this oceanfront home with dog-friendly accommodations (for a nightly pet fee) and a private pool and hot tub! Shark Key Chateau offers room to bring the whole family along. While you'll feel like you're on your own private island, mainland amenities...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Florida and stay in this private dog-friendly home for six for your Key West retreat and enjoy a private pool, wraparound deck, and patio. You'll be tucked away in a quiet Key West neighborhood, surrounded by lush foliage, and you'll be within walking distance of eateries, a market, and...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fresh ocean air, soft sands, and bright sunshine await you at this home in the Florida Keys! You and your loved ones can take in the tropics in peace and comfort, while still being only a short distance from plenty of fun things to do. Tucked away in a quiet neighborhood in the Saddlebunch Keys,...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Small families and close groups of friends will love this dog-friendly home for four in Key West! A shared swimming pool and nearby beach access provide everything you need for a great vacation. Your new home away from home rests comfortably by the city's Old Town, where lots of shops and...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for a budget-friendly home base and plan to spend most of your time enjoying the waves and exploring, this efficient studio is just the ticket. You and one other traveling companion will be in a prime location, within walking distance to the beach and Key West major attractions....
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Terrace
    • Private Outdoor Pool (Unheated)
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Affectionately known as the Captain’s Quarters, this two-story custom-built 3BR/3BA is located on a quiet lane in Bahama Village. This lovely neighborhood exudes a charming old Key West vibe. Please inquire for options. Step out to your back yard for a dip in the private pool, set amid lush...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your island escape will be worth dreaming about when you stay at this affordable studio in central Key West. With a shared balcony for relaxing among the palm trees, dog-friendly accommodations, and beach access nearby, you'll be basking in paradise every second you're here! Located on Duval...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for the perfect Key West vacation rental to host your family reunion or corporate retreat? Your search stops with Curry House Bed & Breakfast, a nine-bedroom, nine-bathroom getaway with historic charm, modern comforts, a private swimming pool, and room for up to 18 guests. Curry House is...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    Sunny condo w/ shared pool & entertainment - central location!1 / 26
    (30)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 1, 2014
    Wonderful location, quiet. In desperate need of upgrades, 2 burner stovetop not fixed but portable one available, ac in bedroom starts and stops every 5 minutes...several...
    Reviewed November 17, 2014
    Nice,good location but no parking onsite 95% of time. Had to park 2 blocks away. Cooktop did not work so had to use portable 110 volt spare.
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    About this property
    Take a remarkable retreat to Key West with this one-bedroom, one-bathroom cottage with a shared pool, and a great central location on the island! Sitting in a quiet location just off Truman Avenue and a few blocks down from Duval Street, you'll be within walking distance of any number of delicious...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cozy, dog-friendly retreat w/ shared hot tubs, patio, great location in Old Town1 / 29
    (2)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 25, 2015
    This place was perfect for our vacation needs. It was close to everything, and the places a bit further away totally doable by renting bikes for the week. We cooked some meals...
    Reviewed August 28, 2014
    This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin...
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    About this property
    Take a break from the ordinary with a visit to this tropical hideaway in the heart of Key West's historic district! Ideal for a romantic getaway, this suite promises comfort, space to relax, and a prime location in Old Town. The family dog is also welcome to join you for an additional nightly fee....
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Dog-friendly condo w/ balcony, shared pool - near shops & restaurants1 / 26
    (11)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Parking
    • Terrace
    • Air Conditioning
    • Balcony
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 3, 2016
    This was at the southern end of Duval so not quite as noisy, which was nice. The restaurant below did play music in the morning which was annoying at times and the rooster would...
    Reviewed March 14, 2015
    The apartment was very comfortable and spacious. It is centrally located and although it's a little noisy at meal times, it is not a problem at night. It does need some minor...
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    About this property
    Experience the beachy retreat you've been searching for at this dog-friendly Key West condo, where you'll enjoy a private balcony, a shared swimming pool, and a wonderful location for exploring. Beautifully positioned to overlook the gardens of Duval Square, this condo offers guests unbeatable...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Slip into vacation mode as you explore Duval Street and dive into the beach scene when you book your trip to this dog-friendly Key West cottage. Featuring street parking, a relaxing shared pool, and a location that puts you right in the heart of the action, up to six guests and a canine companion...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Breezy dog-friendly condo w/ private deck, shared pool/hot tub, & parking space1 / 32
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 5, 2015
    You can book this place if you do not mind occassional airplanes landing and taking off. This is a great place with very friendly staff. The main center of the Island is 5-10...
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    About this property
    Grab your sunglasses, pull up a lounge chair, and relax beside the lagoon-shaped community pool at this upscale Key West condo! From gorgeous tropical landscaping to a private balcony and a dog-friendly policy, this comfortable rental has everything you need for the ultimate Key West experience....
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a piece of Key West's past when you book a stay at this charming ground-floor suite in the historic Curry House Bed & Breakfast! Up to two guests will enjoy a shared on-site pool, home comforts, and a convenient location in the heart of the city. Curry House sits three blocks off of...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience life at the top - the top floor of Curry House Bed & Breakfast, that is! Up to two guests will love staying in this cozy room, which offers a birds-eye view of Key West, access to a shared backyard pool, air conditioning, and more! Curry House sits just three blocks from both bustling...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Gorgeous home w/ private pool, porch & terrace - dogs OK, walk everywhere!1 / 30
    (32)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2016
    Beautiful home. We hated to leave. The property is well kept and the accommodations were beyond our expectations. We had our own private pool to lounge in and enjoy after...
    Reviewed November 11, 2014
    The house was great. Roofs are a little low upstairs but still good enough. Nice patio area and a pool in the backyard. Only a few minutes walking distance from Duval St.
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    About this property
    Find the ultimate in Key West charm at this sun-splashed, dog-friendly cottage with a private pool and garden, a classic wrap-around porch, and an enviable location on a beautiful, historic street. Designed in Key West's famous 'conch cottage' style, this picturesque home sits near the heart of...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
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    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best of Key West's historic district from the comfort of this condo! An upstairs balcony gives you a bird's eye view of the town, and you'll be steps away from shopping, dining, and the beach. Guests staying at this suite will experience historic Duval Street up close, from fine...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Commodore's Cove offers the best of Key West: a prime location and the amenities of home. Up to 12 can stay at this welcoming condo, so bring the whole family along! The family dog is also welcome to join you for an additional nightly fee. Stroll down to historic Duval Street a block away, where...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Historic home in Old Town w/ private pool & detached cottage - dogs OK1 / 43
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 3, 2011
    We spent the month of March at Villa azul in 2008. It was amazing. We discovered Key West in a way I never thought possible...some of our best moments were spent in the oasis...
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    About this property
    Come experience Key West in all its glory when you stay in this dog-friendly historic home featuring a private pool and lush tropical gardens. Your group of up to six will be set for a comfortable and convenient stay, and the detached cottage is the perfect spot for the teenager or grandparent who...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
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    • Internet Access
    • Grill
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If Key West is on your travel itinerary, make this lovely rental for six your home away from home and spend your time lounging by your private pool and spa. Located in Historic Bahama Village, this home is one block away from the world-famous Duval Street, where you can enjoy galleries, shops,...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!1 / 27
    (12)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 4, 2016
    The location is awesome. The kitchen lay out is a train wreck! It was clean and daily towel and linen and linen service was good. Parking ....good luck. Overall it was a fair...
    Reviewed June 5, 2014
    Superb location, ideal for a few days in Key West. Only small but great outside space. Loads of character, only slight negative is the bathroom could do with a little tlc. But...
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    About this property
    Experience Key West in style with this dog-friendly vacation rental in the heart of Old Town! Up to six guests will enjoy a private hot tub and typical home comforts including a private washer/dryer, street parking, and free WiFi. Situated just one block from Duval Street, this cottage has no...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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