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Sugarloaf Key Pet Friendly Rentals

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    Travelers to Sugarloaf Key are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    138 Matching Rentals in Sugarloaf KeyView all 207 rentals
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    Family friendly condo w/ shared pool, hot tub, & complimentary shuttle! Dogs ok!1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Dog-friendly home w/ private pool - walk to the beach and restaurants!1 / 26
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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
    Rental Home - 2 Bedrooms, 3 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 January 1, 2015
    Three generations, nine people, stayed here over Christmas. We each had space to be by ourselves, and we all had space to get together. Nine of us sat around the table in the...
    Reviewed September 3, 2014
    I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
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    About this property
    A large group getaway to Key West starts with this pair of charming cottages, which feature a total five bedrooms, three-and-a-half bathrooms, and a max occupancy of 16. The property also includes a private heated swimming pool, a private hot tub, and dog-friendly accommodations. The cottages sit...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    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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    Sugarloaf Key, Florida Keys 33040
    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
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 26, 2016
    My boyfriend and I stayed here for 4 nights in October. The house was very clean and the check in process was very easy. The house has a small shared pool with the other condos...
    Reviewed July 31, 2014
    The Flamingo Hideaway is a ground floor unit in a small condo complex of renovated, period buildings. This unit is tucked away from the street and right next to the shared pool...
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    About this property
    Surround yourself with peace, tranquility, and seaside fun when you book your trip to this Key West cottage. Enjoy the bubbling hot tub, shared pool, and easy beach access. Nestled in the Palm Gardens condo community in Old Town Key West, this tropical home embraces you with island vibes and a...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Key West and unwind with this comfortable and inviting two-bedroom condo! A shared pool and a private balcony with scenic views of the marsh add to the feeling of relaxation. The family dog is also welcome to join you for an additional nightly fee. This colorful rental is part of the...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!1 / 25
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 27, 2017
    My friends and I have traveled to Key West for the past three years and we always rent through KWVR. Each year we have rented a different property however this property is...
    Reviewed August 18, 2016
    Stayed here with friends. The setup was perfect for our needs - one couple and two singles. My bed was very comfortable. The only thing missing in my room was a mirror! The...
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    About this property
    Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, private pool, furnished patio, and off-street parking for two...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    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
    Wake up every morning to the crisp smell of the ocean when you stay at this cute condo on the shores of Key West! Complete with upscale resort amenities like a shared pool and hot tub, tennis courts, and a private, covered parking space, this comfortable rental is sure to become your new favorite...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Breezy dog-friendly condo w/ private deck, shared pool/hot tub, & parking space1 / 32
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 5, 2015
    You can book this place if you do not mind occassional airplanes landing and taking off. This is a great place with very friendly staff. The main center of the Island is 5-10...
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    About this property
    Grab your sunglasses, pull up a lounge chair, and relax beside the lagoon-shaped community pool at this upscale Key West condo! From gorgeous tropical landscaping to a private balcony and a dog-friendly policy, this comfortable rental has everything you need for the ultimate Key West experience....
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated on the second floor of a historic home, this spacious dog-friendly condo welcomes guests with great amenities and a private hot tub! Soak after a long day in the sunshine, and fire up the gas grill to make full use of the back patio space. You're right around the corner from Duval...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok1 / 28
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 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 March 7, 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the ideal spot for your next large group getaway, then look no further than this grouping of three separate Key West condos. Boasting a shared heated pool and hot tub, and space for up to 12 guests, this home makes it easy for everyone to enjoy all of the local attractions....
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Internet Access
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    • Balcony
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caribbean comforts await at this lovely Key West condo just five miles from the island's historic downtown. With amenities like a private pool and hot tub, tennis courts, a private balcony, and a covered parking spot, this comfortable condo is perfect for anyone who plans to explore the island by...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    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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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Restored historic home w/ private pool & reserved off-street parking - Dogs OK!1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 21, 2017
    My family and 2 of our friends joined us on this trip. The property was clean and close to absolutely everything. We could not have asked for a better place to stay.
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    About this property
    Start planning your Key West vacation when you book this three-bedroom, two-bathroom home. Up to eight guests will spend their vacation days lounging by the private pool, strolling the streets of downtown, and soaking up the Florida sun on soft sand beaches. The family dog is also welcome to join...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    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
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    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
    Rental Home - 2 Bedrooms, 2 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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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the land of sea and sun for your next vacation with this fresh condo in Key West. Featuring one bedroom and one bathroom, entertainment, and an awesome location close to all the action on the waterfront, up to four guests will love it here! The family dog is also welcome to join you for...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Historic house w/ private pool & easy beach access - ideal for groups! Dogs OK!1 / 31
    (1)Very good
    7 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 26, 2016
    We stayed in one of the units at the property (Banana Split). This is a 1 bedroom / 1 bath apartment on the second floor. It has a full kitchen, small sitting area and two decks...
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    About this property
    Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large historic house on Key West. Featuring a private heated pool, four private parking spaces, and a communal area with plenty of room for everyone, this seven-bedroom, eight-and-a-half bathroom house...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 7 Bedrooms, 9 Bathrooms, Sleeps 18
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in the laid-back ambience of the Florida Keys with a stay at this colorful Key West condo! Complete with a shared pool and hot tub, tennis courts, dog-friendly policies, and a reserved parking spot, this comfortable vacation rental will have you relaxed in no time. This...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cute, dog-friendly condo w/ shared hot tub in the heart of historic Key West!1 / 25
    (2)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 5, 2014
    The room was a nice size for two friends. It was not fancy, but clean and well equipped. Another plus was the front porch where we sat and people watched while having coffee or...
    Reviewed July 25, 2014
    The Egret Studio is very close to the Southernmost Point and next door to a Cuban cafe, so I had coffee there every morning. The studio is very clean, well appointed and we...
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    About this property
    Settle in at this conveniently located four-person suite, where you'll have access to a shared hot tub and your own kitchenette! Egret Suite can be rented on its own, or as a part of the entire property for larger groups. The family dog is also welcome to join you for an additional nightly fee. At...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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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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    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.I did not stay in this particular cottage but our guests had rave...
    Reviewed October 7, 2014
    The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15...
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    About this property
    Treat the whole family to a seaside adventure when you book your getaway to this dog-friendly Key West cottage. Boasting a prime location close to beach activities and attractions, as well as a shared pool, this home welcomes up to six guests and a canine companion (for a small nightly fee). This...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
    • Patio
    • Grill
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    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2016
    We rented the entire complex for our wedding. While my husband and I did not stay in this particular cottage we did see the interior and this was used as my "bridal...
    Reviewed May 21, 2015
    We booked this rental through Flipkey. The pictures didn't really show how nice it is. It's not the Ritz, as the other review says, but really very nice. Good kitchen with...
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    About this property
    Treat your group to a tropical getaway at this dog-friendly Key West retreat. Featuring room for up to six guests and a cute canine companion (for a small nightly fee), street parking, a private hot tub, and a shared pool, your vacation promises to be one to remember. This home is nestled in a...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    • Internet Access
    • Patio
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your large group of up to 18 to Key West and stay in this spectacular five-bedroom, three-bath oceanfront home for an unforgettable Florida vacation. Amenities include a private pool, massive deck with seating, lush surrounding gardens, and two private docks, as well as ready access to the...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 18
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cozy, dog-friendly suite w/ shared hot tubs, grill, and patio space to relax1 / 27
    (3)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 23, 2016
    My Daughter and I stayed in Ibis Suite.We Loved the location and the secluded quietness of our suite.The Cuban coffee shop, the Sandwich shop, the Grocery store, the Trolley...
    Reviewed June 2, 2015
    My friends and I stayed at Ibis this past January (all in our mid 20's). I thought I reviewed this property then, but apparently I did not. It was our first trip to Key West and...
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    About this property
    Ibis Suite offers visitors a prime location in Old Town Key West, great amenities, and space to relax. Top off your visit with soaking time in one of the property's hot tubs, and you're well on your way to an optimal Key West experience. Here, you're a few blocks off of famous Duval Street, home...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Parking
    • Internet Access
    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    • Hot Tub
    • Washer
    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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy, dog-friendly retreat w/ shared hot tubs, patio, great location in Old Town1 / 29
    (2)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 25, 2015
    This place was perfect for our vacation needs. It was close to everything, and the places a bit further away totally doable by renting bikes for the week. We cooked some meals...
    Reviewed August 28, 2014
    This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin...
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    About this property
    Take a break from the ordinary with a visit to this tropical hideaway in the heart of Key West's historic district! Ideal for a romantic getaway, this suite promises comfort, space to relax, and a prime location in Old Town. The family dog is also welcome to join you for an additional nightly fee....
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Historic home in Old Town w/ private pool & detached cottage - dogs OK1 / 43
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 3, 2011
    We spent the month of March at Villa azul in 2008. It was amazing. We discovered Key West in a way I never thought possible...some of our best moments were spent in the oasis...
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    About this property
    Come experience Key West in all its glory when you stay in this dog-friendly historic home featuring a private pool and lush tropical gardens. Your group of up to six will be set for a comfortable and convenient stay, and the detached cottage is the perfect spot for the teenager or grandparent who...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Florida and stay in this private dog-friendly home for six for your Key West retreat and enjoy a private pool, wraparound deck, and patio. You'll be tucked away in a quiet Key West neighborhood, surrounded by lush foliage, and you'll be within walking distance of eateries, a market, and...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Cozy, dog-friendly condo with views - walk to beach, dining, & attractions1 / 32
    (6)Average
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 14, 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 July 14, 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
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 28, 2014
    Located right by the Southernmost Hotel and a block off Duval this was a great stepping off point for fun in Key West. Cuban market on the corner for café con leche each...
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    About this property
    Heron Suite's hot tubs access, back patio space, and proximity to the beach set the tone for a lovely stay in Key West's historic district! Well-outfitted for a couple's getaway, this suite offers an excellent location paired with the amenities of home. The family dog is also welcome to join you...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!1 / 27
    (12)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 4, 2016
    The location is awesome. The kitchen lay out is a train wreck! It was clean and daily towel and linen and linen service was good. Parking ....good luck. Overall it was a fair...
    Reviewed June 5, 2014
    Superb location, ideal for a few days in Key West. Only small but great outside space. Loads of character, only slight negative is the bathroom could do with a little tlc. But...
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    About this property
    Experience Key West in style with this dog-friendly vacation rental in the heart of Old Town! Up to six guests will enjoy a private hot tub and typical home comforts including a private washer/dryer, street parking, and free WiFi. Situated just one block from Duval Street, this cottage has no...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Cozy studio condo w/ shared pool & courtyard - easy beach access! Dogs OK!1 / 27
    (2)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Internet Access
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    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 30, 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 November 11, 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
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Kid friendly
    Smoking allowed
    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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Gorgeous home w/ private pool, porch & terrace - dogs OK, walk everywhere!1 / 30
    (32)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2016
    Beautiful home. We hated to leave. The property is well kept and the accommodations were beyond our expectations. We had our own private pool to lounge in and enjoy after...
    Reviewed November 11, 2014
    The house was great. Roofs are a little low upstairs but still good enough. Nice patio area and a pool in the backyard. Only a few minutes walking distance from Duval St.
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    About this property
    Find the ultimate in Key West charm at this sun-splashed, dog-friendly cottage with a private pool and garden, a classic wrap-around porch, and an enviable location on a beautiful, historic street. Designed in Key West's famous 'conch cottage' style, this picturesque home sits near the heart of...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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 February 4, 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 December 8, 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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    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
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Dog-friendly condo w/ balcony, shared pool - near shops & restaurants1 / 26
    (11)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
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    • Terrace
    • Air Conditioning
    • Balcony
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 3, 2016
    This was at the southern end of Duval so not quite as noisy, which was nice. The restaurant below did play music in the morning which was annoying at times and the rooster would...
    Reviewed March 14, 2015
    The apartment was very comfortable and spacious. It is centrally located and although it's a little noisy at meal times, it is not a problem at night. It does need some minor...
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    About this property
    Experience the beachy retreat you've been searching for at this dog-friendly Key West condo, where you'll enjoy a private balcony, a shared swimming pool, and a wonderful location for exploring. Beautifully positioned to overlook the gardens of Duval Square, this condo offers guests unbeatable...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Breezy condo w/ shared pool & hot tub, private parking & great location - dog OK1 / 24
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Terrace
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 19, 2015
    When we got into the condo we had ants on the counter. The next day went to the office to let them know, they had someone come and spray. The sofa bed's mattress needed to be...
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    About this property
    Treat your family to an unforgettable stay in Key West with this dog-friendly condo. Modern conveniences combine with a great location and first-class resort amenities - you'll love this adventure so much, you'll never want to head back home! Courtesy Shuttle available to condo from airport and...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dog-friendly condo w/ private hot tub & shared pool - close to shops & beaches1 / 25
    (16)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 12, 2017
    We couldn't have been happier with Casa Havana for our first trip to Key West! The 2bdr/2bth set up was perfect for 2 couples, and the location couldn't be beat! Easy to walk...
    Reviewed December 10, 2014
    Amazing condo ! Great Staff ! Beautiful place with comfy beds and all the comforts of home and then some ! Hot Tub !!! Full kitchen w/washer and dryer. Gated parking and 2 pools...
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    About this property
    Find a cool, comfortable retreat at this dog-friendly Key West condo, a well-equipped getaway with a private deck and balcony, access to a community swimming pool, and a wonderful location near the heart of the old town. This condo sits among tropical gardens in Duval Square, a location with...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Island condo w/ balcony & great central location - beach nearby! Dogs OK!1 / 25
    (42)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Cable/satellite TV
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    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 17, 2016
    Not even a block off Duval near the Southernmost end of the island (i.e., the quiet end of Duval), this efficiency was a great find. Located in a renovated old house with...
    Reviewed November 10, 2016
    The location is great. Right next to duval street. But it's definitely too small even for 4 persons.... we were walking in each other. One fan wasn't working and in the kitchen...
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    About this property
    This one-bedroom, one-bathroom condo in Key West, featuring entertainment, a wrap-around balcony, and beach access nearby! The family dog is also welcome to join you for an additional nightly fee. Located on the corner of Duval Street and Amelia Street, you'll be close to all the excitement while...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 22, 2017
    Great adult week 1 block away from Duval street. the house was very clean! we had the best time ever!!!
    Reviewed February 7, 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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Family friendly condo w/tennis, shared pool, hot tub, & private balcony- dogs ok1 / 24
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Air Conditioning
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    • Cable/satellite TV
    • Hot Tub
    • Internet Access
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 10, 2016
    The location is nice because it's quiet. The unit and kitchen supplies need updating. The view from the balcony is nice. The pool area is nice.
    Reviewed March 15, 2016
    This 2 bedroom condo in Key West was really great. The staff went out of their way to make us feel welcome. They checked to see if our room was ready and clean early and it...
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    About this property
    Leave your troubles behind and head for the beach with this delightful and dog-friendly Key West condo! Incredible amenities like a shared pool and hot tub, tennis courts, and a private balcony with views of the marsh ensure you'll have a vacation to remember. Located in the upscale Sunrise Suites...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tucked away in the trees, this Key West hideaway is a great choice for couples or small families. Shared hot tub access and patio space will have you feeling right at home in Pelican Suite! Take a walk a couple blocks down and you're at the beach, toes in the sand. Local staple Louie's Backyard...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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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
    • Parking
    • Balcony
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 13, 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 September 16, 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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    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
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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