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Sugarloaf Key Holiday Rentals

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    Travellers to Sugarloaf Key are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 207 Rentals in Sugarloaf Key
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    Comfortable condo w/ shared pool, private balcony, and beach access1 / 26
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Stylish, dog-friendly condo with shared pool, hot tub, and complimentary shuttle1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Dog-friendly home w/ private pool - walk to the beach and restaurants!1 / 26
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Terrace
    • Washer
    • Balcony
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 February 2018
    Had a great surprise birthday weekend in Key West. The house was fantastic! Very clean and bigger than the pictures make it seem. Loved the heated pool, and close walk to Duval...
    Reviewed 23 January 2017
    3 levels of beautifully decorated accommodations! Walking distance to famous Duval St, bars, restaurants and shopping. Loved it!
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    About this property
    Escape to the Florida Keys for a relaxing vacation in this three-bedroom, two-and-a-half bath home for eight (six comfortably) with a private pool and walking distance to the beach and Duval Street. And your favorite canine friend is also welcome for a small nightly fee. This rental is mere blocks...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    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
    • Internet Access
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    • Hot Tub
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    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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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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 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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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Dog-friendly, tropical escape with central location, hot tub, and shared pool1 / 26
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Hot Tub
    • Grill
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    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 December 2016
    My boyfriend and I stayed here for 4 nights in October. The house was very clean and the check in process was very easy. The house has a small shared pool with the other condos...
    Reviewed 31 July 2014
    The Flamingo Hideaway is a ground floor unit in a small condo complex of renovated, period buildings. This unit is tucked away from the street and right next to the shared pool...
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    About this property
    Surround yourself with peace, tranquility, and seaside fun when you book your trip to this Key West cottage. Enjoy the bubbling hot tub, shared pool, and easy beach access. Nestled in the Palm Gardens condo community in Old Town Key West, this tropical home embraces you with island vibes and a...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Parking
    • Terrace
    • Internet Access
    • 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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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Peaceful, dog-friendly home in a residential neighborhood w/ a shared pool1 / 26
    (3)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Washer
    • Air Conditioning
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    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.I did not stay in this particular cottage but our guests had rave...
    Reviewed 7 October 2014
    The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15...
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    About this property
    Treat the whole family to a seaside adventure when you book your getaway to this dog-friendly Key West cottage. Boasting a prime location close to beach activities and attractions, as well as a shared pool, this home welcomes up to six guests and a canine companion (for a small nightly fee). This...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your Key West vacation in style here at this high-end house with a private hot tub! There's plenty of room for everybody in this house's eight bedrooms, and you're steps away from the ocean. Key West's most popular attractions surround this home - walk down to Mallory Square a few blocks...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key West condo! A community pool and hot tub, tennis courts, a parking space, and pool views from your private balcony add to an atmosphere of luxury and total relaxation. This...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dog-friendly, colorful cottages w/ pool & hot tub in a fabulous location!1 / 47
    (14)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2015
    Three generations, nine people, stayed here over Christmas. We each had space to be by ourselves, and we all had space to get together. Nine of us sat around the table in the...
    Reviewed 3 September 2014
    I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
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    About this property
    A large group getaway to Key West starts with this pair of charming cottages, which feature a total five bedrooms, three-and-a-half bathrooms, and a max occupancy of 16. The property also includes a private heated swimming pool, a private hot tub, and dog-friendly accommodations. The cottages sit...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Slip into vacation mode as you explore Duval Street and dive into the beach scene when you book your trip to this dog-friendly Key West cottage. Featuring street parking, a relaxing shared pool, and a location that puts you right in the heart of the action, up to six guests and a canine companion...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 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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    • Cable/satellite TV
    • Terrace
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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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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    • Cable/satellite TV
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    • Air Conditioning
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2017
    Clean, quaint, and comfortable. The office help was great, and cleaning service was good. This is close to all of the action while maintaining a peaceful night's sleep.
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    About this property
    Up to four guests can enjoy all the fun of Key West at this updated home complete with a shared pool with waterfall, and lush, outdoor seating area. As an added bonus, this home comes with private, off-street parking for one vehicle - a real luxury in the Keys! Dogs are allowed for a small nightly...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Parking
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    • 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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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Hot Tub
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    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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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok1 / 34
    (50)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    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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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Dog-friendly condo w/private hot tub & shared pool - walk to Duval St!1 / 30
    (36)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 March 2016
    My husband and I stayed at this condo for 2 nights with another couple. The location was great. Although we were near the main street, this unit (R9) was quiet (except for the...
    Reviewed 19 January 2015
    We've been to Key West a number of times, but never in January. We're not party animals or lovers of noise, so I knew to avoid the Mallory Square end of things. This condo was...
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    About this property
    Bask in the allure of old town Key West at this dog-friendly condo, where you'll have a private hot tub and deck, a community swimming pool, and enviable access to beaches, shops, and wonderful restaurants. Located mere steps from Duval Street and verdant tropical gardens, this Duval Square condo...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    Wake up every morning to the crisp smell of the ocean when you stay at this cute condo on the shores of Key West! Complete with upscale resort amenities like a shared pool and hot tub, tennis courts, and a private, covered parking space, this comfortable rental is sure to become your new favorite...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Affectionately known as the Captain’s Quarters, this two-story custom-built 3BR/3BA is located on a quiet lane in Bahama Village. This lovely neighborhood exudes a charming old Key West vibe. Please inquire for options. Step out to your back yard for a dip in the private pool, set amid lush...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2017
    My weekend stay was fabulous. Condo location was perfect. Beautiful updated kitchen and living room. Bedrooms were perfect. I would 100% recommend.. Look forward to coming back.
    Reviewed 16 September 2015
    Very nice place in a great location. Close to everything and very convenient. Staff was excellent, place was clean and service by the concierge was top notch. I would stay...
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    About this property
    Surround yourself with the historic charms of Key West at this dog-friendly penthouse, a spacious South Florida escape with a private hot tub, a deck and balcony for evening cocktails, and access to a lovely community swimming pool. You'll find this comfortable condo in Duval Square, offering...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Slip away to the Florida Keys with a stay at this two-bedroom, two-bathroom condo with a private patio, beautiful tropical landscaping, and a shared pool for cooling off! This condo is part of the high-end Sunrise Suites Resort in Key West. With a fabulous location just three miles from the city...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the tropical warmth of Key West at this two-bedroom condo, where you'll enjoy a beautiful community swimming pool, a private patio dining area, and an outstanding location close to beaches, shops, and restaurants. This condo is located in the lovely Truman Annex neighborhood, offering...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cheery beach getaway near local attractions, w/shared pool & easy beach access1 / 56
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2014
    Highly recommend this facility to anyone who is looking for a conveniently located, quiet, easily acessable 2 bedroom / 2 bath condo. Our week stay was everything we could...
    Reviewed 12 May 2014
    Three friends that I have known since first grade and I traveled to Key West for a week to celebrate the year we all turn 60. Stayed at Shipyard Perch. it was perfect. The 2...
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    About this property
    Treat yourself to a stress-free vacation filled with sun-soaked days when you book your trip to this Key West condo. With room for up to four guests to a shared pool and beach lifestyle, this home will make it easy to slip into vacation mode! Located in the Truman Annex, a quick five minute walk...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Internet Access
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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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Island-themed, dog-friendly home in a residential neighborhood w/ a shared pool1 / 24
    (2)Very good
    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 22 August 2016
    Love the place! Location was good. There was an issue with ants in the kitchen. Also, I was issued 3 keys and 1 of the keys was not for our place. Changed the key with...
    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...
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    About this property
    Get away from the stress of the daily grind with a trip to this contemporary Key West home. Offering street parking, access to a shared pool, room for up to four guests, and a charming island-themed ambiance, this home will make it easy to slip into vacation mode. The family dog is also welcome to...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Quiet, dog-friendly getaway in a residential neighborhood with a shared pool1 / 25
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    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 cottage but our guests had rave reviews and I...
    Reviewed 5 March 2015
    My family and I stayed at Toon Hall the last week in February and had a blast. The home is located close to Higgs Beach, a few blocks away, and a few blocks from Duvall St. The...
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    About this property
    Grab your sunglasses, your beach towel, and charge your camera for a visit to this Key West home, once the winter home of Pulitzer Prize-winning cartoonist Jeff MacNelly. Offering a family-friendly atmosphere and a pristine shared pool, this home gives you the chance to experience the best of...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 2016
    This was at the southern end of Duval so not quite as noisy, which was nice. The restaurant below did play music in the morning which was annoying at times and the rooster would...
    Reviewed 14 March 2015
    The apartment was very comfortable and spacious. It is centrally located and although it's a little noisy at meal times, it is not a problem at night. It does need some minor...
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    About this property
    Experience the beachy retreat you've been searching for at this dog-friendly Key West condo, where you'll enjoy a private balcony, a shared swimming pool, and a wonderful location for exploring. Beautifully positioned to overlook the gardens of Duval Square, this condo offers guests unbeatable...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    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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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 2016
    We stayed in one of the units at the property (Banana Split). This is a 1 bedroom / 1 bath apartment on the second floor. It has a full kitchen, small sitting area and two decks...
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    About this property
    Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large historic house on Key West. Featuring a private heated pool, four private parking spaces, and a communal area with plenty of room for everyone, this seven-bedroom, eight-and-a-half bathroom house...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 18
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    Restored historic home w/ private pool & reserved off-street parking - Dogs OK!1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 2017
    My family and 2 of our friends joined us on this trip. The property was clean and close to absolutely everything. We could not have asked for a better place to stay.
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    About this property
    Start planning your Key West vacation when you book this three-bedroom, two-bathroom home. Up to eight guests will spend their vacation days lounging by the private pool, strolling the streets of downtown, and soaking up the Florida sun on soft sand beaches. The family dog is also welcome to join...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 February 2017
    We stayed at this cottage for a couple nights. It was cozy and well kept. The kitchen had everything you'd need to cook an average meal. The cottage definitely could have used a...
    Reviewed 8 December 2014
    The home was clean, centrally located. Also, safe. will be coming back and using you guys again on our next trip to key west!
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    About this property
    Enjoy your very own piece of Key West at this one-bedroom cottage, a lovely little home with dog-friendly accommodations, a charming front porch, and an ideal location close to restaurants, nightlife, and white sand beaches. You'll find this cheerful cottage in Simonton Court, a complex that sits...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 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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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Historic vacation rental with a private pool - dog-friendly!1 / 25
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2015
    My husband and I stayed here with 2 other couples. The location was absolutely perfect for walking or biking to anywhere on the island. The pool and outdoor area were also...
    Reviewed 29 July 2014
    This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management...
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    About this property
    A sun-soaked getaway in the Florida Keys awaits you when you stay at this beautiful dog-friendly vacation rental! Lounge in comfort by the private pool or stay inside and enjoy the air conditioning while you browse the cable channels on the flatscreen TV. However you spend your vacation days,...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • 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
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your family and friends (and a dog!) along for the ride to this home in Florida's sunny Key West! Between the great location and modern amenities, everyone in your group will find something to love. Courtesy Shuttle available to condo from airport and ferry terminal. If you'd like to spend...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ease into the pleasures of a tropical vacation with this one-bedroom, one-bathroom condo in Key West. With a charming atmosphere, entertainment, and four private parking spaces to save you any headaches, you'll speak nothing but praise during your stay in paradise! Located in the downstairs of a...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take the worry out of coordinating housing for your next big family reunion or holiday celebration and reserve this entire Key West property. Consisting of five separate rentals all sharing a large, outdoor gathering area, your very own swimming pool, sundeck, and even a bar, up to 22 people can...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 22
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    Comfortable condo living w/ shared pool & lush gardens - in Old Town, dogs ok1 / 25
    (21)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 October 2015
    The location is perfect, almost in the middle of it all. Downstairs are nice restaurants. If you don’t want to cook, go to NY Pasta Garden down stairs. They serve a fantastic...
    Reviewed 13 September 2015
    The check in process for KWVR was fast and easy. The office staff is very friendly and helpful. We found Casa Bonita spacious for the four of us and our dog. The kitchen is...
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    About this property
    Experience all that Old Town Key West has to offer at this beautiful, roomy condo located right off Duval Street. Featuring a large, shared swimming pool, lush, tropical gardens, private, covered parking, and space for up to six lucky guests, this vacation rental is ready-made for a fun, family...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Centrally located home w/ private pool 3 blocks to Duval St - dogs OK!1 / 25
    (9)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • Grill
    • DVD Player
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 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
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Classic Key West cottage featuring shared pool, courtyard, covered front porch1 / 27
    (17)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2017
    We stayed here after having a rough go of it in Miami and we fell in love. My kids said "Mom we should have stayed here the whole time, this place is awesome." The pool...
    Reviewed 10 September 2015
    Beautifully decorated Old Key West home. Our kids (12, 5) loved seeing the Iguana in the courtyard. The pool was nice to relax in after a day of sightseeing. Beds were...
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    About this property
    Part of the Papa's Hideaway complex, this charming, old Key West cottage is an ideal home away from home for that next vacation to the Southernmost Point. Up to six guests can enjoy this recently updated home complete with a high-end kitchen, loads of modern amenities, a shared swimming pool,...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dog-friendly condo with tennis, shared pool, hot tub, and private balcony1 / 24
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Hot Tub
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    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 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 15 March 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful views, resort amenities, and a dog-friendly policy await when you book your stay at this charming condo on the eastern shore of Key West! Located within the upscale Sunrise Suites Resort community, this excellent rental is perfectly situated for you to explore Key West by day and relax...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Terrace
    • Balcony
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Swap out the winter blues for the incredible blue of Key West's sky, and book a stay in this delightful condo! With resort amenities like tennis courts, a shared pool and hot tub, and lush tropical landscaping, you'll be back in summer mode in no time. One dog is allowed for a small nightly fee....
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful condo with a deck/patio & shared pool - walk to beaches, Duval & more!1 / 23
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • DVD Player
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    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 2015
    We visited the Annex for Fantasy Fest a few years back. The location is perfect! Close enough to the action of the main streets, but private enough for some peace when you're...
    Reviewed 19 January 2015
    Great location; we loved having the back gate for direct access out to Angela Street and the close proximity to the Green Parrot and Blue Heaven - two of our Key West favorites...
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    About this property
    Find the best of Key West at your doorstep with this beautiful two-bedroom condo, a lovely South Florida escape with a private deck and patio, a shared swimming pool, and a wonderful location close to restaurants, beaches, and more! Perfectly located between Truman Annex and Bahama Village, this...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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