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Sugarloaf Key Holiday Rentals

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    Travellers to Sugarloaf Key are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    All 207 Rentals in Sugarloaf Key
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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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    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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    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
    • Terrace
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    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 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 28 July 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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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 9 January 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 16 November 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 February 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 23 January 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Patio
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    Suitability
    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
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
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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
    Holiday Rental House - 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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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 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 19 January 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    • Balcony
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    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 1 January 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 3 September 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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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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
    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
    Holiday Rental House - 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
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 December 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 31 July 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
    Holiday Rental House - 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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    • Terrace
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    • Washer
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • Balcony
    • Cable/satellite TV
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    We were very pleased to locate this little home with a shared pool in the heart of the historic district. We were a group of 4 so we were looking for a clean, comfortable, and...
    Reviewed 7 March 2017
    Clean, quaint, and comfortable. The office help was great, and cleaning service was good. This is close to all of the action while maintaining a peaceful night's sleep.
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    About this property
    Up to four guests can enjoy all the fun of Key West at this updated home complete with a shared pool with waterfall, and lush, outdoor seating area. As an added bonus, this home comes with private, off-street parking for one vehicle - a real luxury in the Keys! Dogs are allowed for a small nightly...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 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
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 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 21 May 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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 26 May 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
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 18
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 21 April 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 7 October 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
    Holiday Rental House - 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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 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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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Penthouse w/ private hot tub & shared pool - close to beaches, dogs OK.1 / 33
    (28)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2017
    My weekend stay was fabulous. Condo location was perfect. Beautiful updated kitchen and living room. Bedrooms were perfect. I would 100% recommend.. Look forward to coming back.
    Reviewed 16 September 2015
    Very nice place in a great location. Close to everything and very convenient. Staff was excellent, place was clean and service by the concierge was top notch. I would stay...
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    About this property
    Surround yourself with the historic charms of Key West at this dog-friendly penthouse, a spacious South Florida escape with a private hot tub, a deck and balcony for evening cocktails, and access to a lovely community swimming pool. You'll find this comfortable condo in Duval Square, offering...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 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 18 September 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 12 May 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    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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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Bask in the tropics of Key West at this dog-friendly cottage with a private heated pool and a lush backyard garden. This lovely cottage is located in Old Town near Duval Street, minutes from restaurants, museums, and the daily sunset celebration at Mallory Square. Stay cool with air conditioning,...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Romantic & elegant studio-style cottage w/ private hot tub - dog-friendly!1 / 26
    (3)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2016
    As far as the accommodation is concerned, the location is unsurpassed. The cottage is clean, comfortable and well appointed. Sadly what let's the place down are the...
    Reviewed 11 November 2015
    This is the second time we've stayed in this rental complex. The first time upstairs and now this time in the back. The location off of Whitehead is perfect for everything we...
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    About this property
    Experience the best of Key West from the comfort of this charming studio-style cottage. A private hot tub, dog-friendly accommodations, and modern conveniences including free WiFi and a shared washer/dryer make this vacation rental perfect for everything from a laid-back retreat to an...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    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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    Dog-friendly condo w/ shared pool, full kitchen & parking - central location!1 / 27
    (2)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    The location was fantastic. We were there with a large group and rented out the entire house (including this 2BR/2.5BA main house plus all of the other 1BR guest suites). All of...
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    About this property
    The tranquil majesty of Key West will be at your fingertips when you stay at this homey two-bedroom, two-and-a-half-bathroom condo, with a shared pool and a great location near the beach! Part of Banana's Foster Guest House in the center of downtown, you'll be within easy walking distance from...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Upper-floor suite in historic home w/ shared on-site pool & semi-private veranda1 / 24
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    Arrived and all paperwork was ready, easy to communicate thru emails and even phone calls, great customer service. Place was quaint and cute, felt comfortable and safe. Room...
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    About this property
    If you're planning a romantic Key West vacation for you and your sweetheart, this charming Curry House suite might be just what you're looking for! Up to two guests will enjoy lounging by the shared on-site pool, people-watching on the semi-private veranda, and relaxing in the shared sitting rooms...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This beautiful main-floor suite is the largest room in the historic Garden House Bed & Breakfast and features a semi-private porch, access to the shared pool, and a desk, making it ideal for a traveling couple or a writer's retreat. The Garden House sits just a few blocks away from both Duval...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Charming tropical getaway w/ shared pool, sundeck, and bar - near Duval Street1 / 24
    (4)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 November 2014
    Papa's Hideaway is a hidden paradise! It is beautiful and comfortable and close to everything. The bed was extremely comfortable and furnished with everything we needed for a...
    Reviewed 18 March 2014
    Loved the location to everything,walking distance and even had parking included in the cost of rental...made me feel relaxed instantly,loved hanging out at the pool and meeting...
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    About this property
    This second-floor studio has a private outdoor seating area and plenty of space for up to four guests. Spend time at home splashing in the shared pool or catch some rays on the sundeck. Located in a residential neighborhood, this rental is just a short walk from Duval Street for the area's best...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Ground-floor studio w/ shared heated pool - walking distance to everything!1 / 24
    (1)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 June 2016
    Although the room I stayed in (The Gecko Grotto-Garden House) was a tad bit small it was quite cozy and welcoming. The description said that there would be a microwave and...
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    About this property
    You and your loved one will be close to the action when you stay at this charming two-person suite in the historic Garden House Bed & Breakfast. Whether you're strolling the streets of Key West, relaxing in the comfort of your spacious room, or lounging by the shared heated pool, you're sure to...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Dog-friendly condo w/ porch & Old Town location - walk to beaches & restaurants!1 / 26
    (25)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 May 2017
    Great adult week 1 block away from Duval street. the house was very clean! we had the best time ever!!!
    Reviewed 7 February 2015
    For $1700 for 5 nights, I expected a little more. First, I considered doing laundry on the last day, but the dryer door doesn't close (as evidenced by the tape marks all over it...
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    About this property
    Enjoy one of the most enviable locations in Key West when you escape to this two-bedroom condo, where you'll have a dog-friendly interior, a private covered porch, and wonderful access to beaches, restaurants, and the Old Town. This gated property sits in the heart of Old Town Key West, just one...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the tropical warmth of Key West at this two-bedroom condo, where you'll enjoy a beautiful community swimming pool, a private patio dining area, and an outstanding location close to beaches, shops, and restaurants. This condo is located in the lovely Truman Annex neighborhood, offering...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Great for families! Free shuttle service, private patio, shared pool & hot tub!1 / 24
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay cool on your next trip to Key West with a stay at this delightful condo with a private balcony, a shared pool, and a complimentary shuttle between the rental and many of Key West's popular attractions. Located just minutes away from beaches, marinas, scuba shops, and the Key West...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy cottage w/ porch & great walking location - close to beach, small dogs OK!1 / 29
    (22)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 February 2017
    We stayed at this cottage for a couple nights. It was cozy and well kept. The kitchen had everything you'd need to cook an average meal. The cottage definitely could have used a...
    Reviewed 8 December 2014
    The home was clean, centrally located. Also, safe. will be coming back and using you guys again on our next trip to key west!
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    About this property
    Enjoy your very own piece of Key West at this one-bedroom cottage, a lovely little home with dog-friendly accommodations, a charming front porch, and an ideal location close to restaurants, nightlife, and white sand beaches. You'll find this cheerful cottage in Simonton Court, a complex that sits...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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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
    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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all and head to Key West for a sun-filled vacation with this two-bedroom, two-bath condo for six and enjoy easy access to restaurants, attractions, and the beach. You can also bring your beloved dog along for a small nightly fee! You'll be located on the northeast corner of Key...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal for a romantic getaway to Key West, this cozy, tropical-themed studio offers a shared swimming pool, outdoor seating and dining areas, a sun deck, and convenient access to exciting destinations like Duval Street, marinas, historic landmarks, and local beaches. The Garden House offers private,...
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    Location Information
    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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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 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 11 November 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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 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 14 March 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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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