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Holiday Homes in Sugarloaf

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    All 212 Rentals in Sugarloaf
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    Sugarloaf
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sugarloaf
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Sugarloaf
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sugarloaf
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Bow Channel Manor and step back in time to Old Florida! You'll find this plantation style home remeniscent of Florida past! Enjoy family-style vacationing on a private 4 acre parcel of land on Upper Sugarloaf Key. The grounds are like a playground. There is a full-size heated pool with...
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    33042, Sugarloaf, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sugarloaf
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Balcony
    • Waterfront
    • Terrace
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This pet-friendly home completed in 2012 has 5 rooms, 3 king size beds, and 4 twins plus a twin sofa bed and three full bathrooms. The home has a huge kitchen with custom made wood cabinets and top of the line stainless steel appliances including an indoor gas grill and a standing freezer: to keep...
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    33042, Sugarloaf, Florida Keys
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    The following rentals are within 10 kilometres of Sugarloaf.
    Family friendly condo w/ shared pool, hot tub, & complimentary shuttle! Dogs ok!1 / 27
    (1)Excellent
    Sugarloaf Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the sunshine and soft sands of the Florida Keys with this amazing dog-friendly home in Sunrise Suites Resort in Key West with a shared pool and a complimentary shuttle. With the resort's complimentary shuttle, it's easy to get to the airport and the ferry terminal. Enjoy bird watching...
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    33040, Sugarloaf Key, Florida Keys
    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
    Sugarloaf Key
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Dog-friendly home w/ private pool - walk to the beach and restaurants!1 / 26
    (2)Excellent
    Sugarloaf Key
    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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    • Balcony
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sugarloaf Key
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this gorgeous Sugarloaf Key vacation home, you'll have five spacious bedrooms (including two master suites)! Enjoy beautiful Gulf views set over three acres, offering privacy for a memorable Florida escape. It's even dog-friendly! Just 18 miles from Key West, this location offers easy access to...
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    33042, Sugarloaf Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!1 / 25
    (17)Very good
    Sugarloaf Key
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 January 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 18 August 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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Comfortable condo w/ shared pool, private balcony, and beach access1 / 26
    (7)Very good
    Sugarloaf Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
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    • Terrace
    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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sugarloaf Key
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sugarloaf Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Hot Tub
    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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sugarloaf Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sugarloaf Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
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    • Terrace
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    • Cable/satellite TV
    • Hot Tub
    • Washer
    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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    33040, Sugarloaf Key, Florida Keys
    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
    Sugarloaf Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Patio
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    • Parking
    Suitability
    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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sugarloaf Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Internet Access
    • Hot Tub
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
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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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sugarloaf Key
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Patio
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    • 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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Dog-friendly, colorful cottages w/ pool & hot tub in a fabulous location!1 / 47
    (14)Excellent
    Sugarloaf Key
    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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    Beautiful condo with a deck/patio & shared pool - walk to beaches, Duval & more!1 / 23
    (4)Very good
    Sugarloaf Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sugarloaf Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sugarloaf Key
    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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Four condos w/ entertainment, private parking & beach nearby - great for groups!1 / 24
    (2)Very good
    Sugarloaf Key
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Balcony
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    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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Sugarloaf Key
    Studio, 1 Bathroom, Sleeps 2 Quick View
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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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    33040, Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Historic house w/ private pool & easy beach access - ideal for groups! Dogs OK!1 / 31
    (1)Very good
    Sugarloaf Key
    7 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 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
    Sugarloaf Key
    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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sugarloaf Key
    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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    33040, Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Dog-friendly, tropical escape with central location, hot tub, and shared pool1 / 25
    (3)Very good
    Sugarloaf Key
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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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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    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sugarloaf Key
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Internet Access
    • Parking
    • Washer
    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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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    Sugarloaf Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Parking
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • 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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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sugarloaf Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Hot Tub
    • Cable/satellite TV
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    • Internet Access
    Suitability
    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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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Restored historic home w/ private pool & reserved off-street parking - Dogs OK!1 / 24
    (1)Excellent
    Sugarloaf Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
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    • Cable/satellite TV
    Suitability
    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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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 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
    Sugarloaf Key
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Terrace
    • Internet Access
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    • Balcony
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    Suitability
    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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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sugarloaf Key
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    • Cable/satellite TV
    Suitability
    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
    33040, Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Dog-friendly home w/ detached cottage, private pool, & walk to beach!1 / 24
    (1)Excellent
    Sugarloaf Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Cable/satellite TV
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    • Patio
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2014
    The place was really nice and the staff was very easy to work with. It was a very good vacation and would definitely like to stay there again.
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    About this property
    Come to Key West and stay in this dog-friendly accommodation with two separate living quarters, a private pool, walking distance to the beach, and close proximity to all the major attractions. This home is within walking distance to famous Duval Street and its shops, restaurants, and bars. Higgs...
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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sugarloaf Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Cable/satellite TV
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    • Patio
    • Washer
    Suitability
    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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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sugarloaf Key
    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Terrace
    • Air Conditioning
    • Internet Access
    • Balcony
    • Cable/satellite TV
    Suitability
    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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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    Sugarloaf Key
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • 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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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Cozy, dog-friendly retreat w/ shared hot tubs, patio, great location in Old Town1 / 29
    (2)Excellent
    Sugarloaf Key
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
    • Patio
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 June 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 28 August 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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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Cozy studio condo w/ shared pool & courtyard - easy beach access! Dogs OK!1 / 27
    (2)Very good
    Sugarloaf Key
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2016
    Loved the stay here. Close to Duvall. Could walk to anywhere on the island including historical sites, any restaurant. Centrally located. Rooms very clean and spacious. Only...
    Reviewed 11 November 2014
    This place was perfect for what we were looking for:Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
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    About this property
    Let time wash over you in gentle waves while you relax in the sunny paradise of Key West at this cozy studio condo, offering access to a shared pool, courtyard, and an easy walk to the soft sandy beach. Located in the heart of downtown Key West as part of the larger Banana Foster's Guest House,...
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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok1 / 34
    (50)Very good
    Sugarloaf Key
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Grill
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 December 2014
    The rental is great and in an excellent location. We had a group of 6 and had no issues. Note: unlike some rentals there is nothing in the house if you plan to cook. You...
    Reviewed 24 July 2014
    Everything was easy and perfect check in wise. Rooms were clean. Will stay here again. Walked to all bars and loved the tall ceilings.
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    About this property
    Immerse yourself in the island lifestyle when you book this Key West accommodation, comprised of a two-bedroom house and a separate one-bedroom pool house. Featuring a private heated pool, a private parking spot, and an outdoor shower, this home gives you the chance to unwind. Four dogs are...
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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Cozy, dog-friendly condo with views - walk to beach, dining, & attractions1 / 32
    (6)Average
    Sugarloaf Key
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Internet Access
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 December 2016
    Walking distance to restaurants and attractions. The room was clean and well appointed. Location was very private. Check in and out was easy and within walking distance. 4...
    Reviewed 14 July 2014
    Coral Cove was a great place to stay for 2 people. We only stayed for one night, which was just enough. It was a little cramped, but was a safe and comfortable place to sleep...
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    About this property
    Escape to Key West for a romantic getaway for two and walk to the beach, dining, and other attractions when you make this cozy, efficiency studio yours. You'll be located in a quiet neighborhood and surrounded by tropical vegetation and decking for great views. You'll be within walking distance to...
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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Sugarloaf Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Parking
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Leave your worries behind with a relaxing trip to the Florida Keys courtesy of this lovely vacation home! This traditional home in Key West features modern amenities and a location perfect for sightseeing. Nestled in Key West's old town, this home for four puts you only a few blocks from both...
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    Location Information
    33040, Sugarloaf Key, Florida Keys
    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
    Sugarloaf Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Parking
    • Cable/satellite TV
    • Hot Tub
    • Terrace
    • Internet Access
    • Air Conditioning
    • Washer
    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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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Historic, dog-friendly cottage in the heart of Key West w/ private hot tub1 / 27
    (16)Very good
    Sugarloaf Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Internet Access
    • Parking
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2016
    This house had a wonderful location. It was very easy to walk to Duval Street and the Southernmost Point. The beds were comfortable, but the house inside and out needs...
    Reviewed 1 July 2014
    Our first visit to the Keys celebrating our 28th anniversary with our adult children, (3 couples) this historic cottage slept all 6 of us very comfortably; in fact, the most...
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    About this property
    If you're looking for a convenient home base for your Key West adventure, consider this two-bedroom, one-bathroom vacation rental. Up to six guests will enjoy the convenient location, a private hot tub, a fully equipped kitchen, and more! The family dog is also welcome to join you for an additional...
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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sugarloaf Key
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Hot Tub
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This colorful dog-friendly Florida home has everything you need for an unforgettable vacation, with a private swimming pool and hot tub and walking distance from the beach. Your home sits only a few blocks away from the soft sands and warm waters of Higgs Beach. If you'd prefer some shopping and...
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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Sugarloaf Key
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amenities like a shared pool, dog-friendly accommodations, and a fantastic location all make this home perfect for your next trip to the Florida Keys! Your new getaway of choice is only a block away from Duval Street, right near Key West's Old Town. Shops and restaurants are easily accessible - as...
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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Sugarloaf Key
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Air Conditioning
    • Washer
    • Grill
    • Cable/satellite TV
    • Internet Access
    Suitability
    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
    33040, Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Centrally located home w/ private pool 3 blocks to Duval St - dogs OK!1 / 25
    (9)Very good
    Sugarloaf Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • Grill
    • DVD Player
    • Patio
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2016
    We spent January and February at Casa 625 and loved it. There were definitely some issues with the house when we arrived, but once Rick, the rental property manager, got...
    Reviewed 23 December 2013
    The house is my perfect idea of what a Key West Conce Cottage should be. With Dade County pine walls, heated pool, all modern conveniences and perfect location for quite and...
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    About this property
    Swim in the private pool, head to downtown Key West to soak up the sights, or relax in a breezy dog-friendly home - with this amazing cottage, everything is possible! Your new home away from home sits on a hill only a few blocks from the beating heart of Key West. Shopping, dining, and more can be...
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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Romantic & elegant studio-style cottage w/ private hot tub - dog-friendly!1 / 26
    (3)Very good
    Sugarloaf Key
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Internet Access
    • Hot Tub
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    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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    Location Information
    33040, Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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