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Sugarloaf Key Vacation Rentals

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    Sugarloaf Key is popular with travelers just like you. Don’t let them get your perfect place first—book today!
    All 59 Rentals in Sugarloaf Key
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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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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    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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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the sunshine and soft sands of the Florida Keys with this amazing dog-friendly home in Sunrise Suites Resort in Key West with a shared pool and a complimentary shuttle. With the resort's complimentary shuttle, it's easy to get to the airport and the ferry terminal. Enjoy bird watching...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dog-friendly home w/ private pool - walk to the beach and restaurants!1 / 27
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 28, 2018
    Had a great surprise birthday weekend in Key West. The house was fantastic! Very clean and bigger than the pictures make it seem. Loved the heated pool, and close walk to Duval...
    Reviewed January 23, 2017
    3 levels of beautifully decorated accommodations! Walking distance to famous Duval St, bars, restaurants and shopping. Loved it!
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    About this property
    Escape to the Florida Keys for a relaxing vacation in this three-bedroom, two-and-a-half bath home for eight (six comfortably) with a private pool and walking distance to the beach and Duval Street. And your favorite canine friend is also welcome for a small nightly fee. This rental is mere blocks...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    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
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    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 cottage but our guests had rave reviews and I...
    Reviewed March 5, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Contemporary beachside escape with shared pool and close to local attractions1 / 25
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 31, 2014
    We had a wonderful time staying in Key West. The condo location was perfect. We walked everywhere. The beds were comfortable, and although the kitchen is very small, it was...
    Reviewed March 12, 2014
    This place is a very nice place to stay.Key West Vacation Rentals are very helpful and easy to reach.The location is perfect just 5 minutes walk to Duval Street and 15 min to...
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    About this property
    Grab your sunglasses, bathing suit, and sunscreen and get ready to dive into the beach lifestyle when you book this Key West condo. Boasting a shared pool to stay cool, this home gives you the chance to slip into vacation mode with ease. This condo is just two blocks from Fort Zachary Taylor...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 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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    • Cable/satellite TV
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    • Terrace
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 18, 2014
    Highly recommend this facility to anyone who is looking for a conveniently located, quiet, easily acessable 2 bedroom / 2 bath condo. Our week stay was everything we could...
    Reviewed May 12, 2014
    Three friends that I have known since first grade and I traveled to Key West for a week to celebrate the year we all turn 60. Stayed at Shipyard Perch. it was perfect. The 2...
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    About this property
    Treat yourself to a stress-free vacation filled with sun-soaked days when you book your trip to this Key West condo. With room for up to four guests to a shared pool and beach lifestyle, this home will make it easy to slip into vacation mode! Located in the Truman Annex, a quick five minute walk...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Paradise awaits when you book your next Florida vacation at this lovely two-bedroom condo on the sunny shores of Key West. With lush tropical landscaping and exclusive resort amenities like a pool, hot tub, and tennis courts, you'll never want to leave! This rental is located in the upscale resort...
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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
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2016
    We rented the entire complex for our wedding. While my husband and I did not stay in this particular cottage we did see the interior and this was used as my "bridal...
    Reviewed May 21, 2015
    We booked this rental through Flipkey. The pictures didn't really show how nice it is. It's not the Ritz, as the other review says, but really very nice. Good kitchen with...
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    About this property
    Treat your group to a tropical getaway at this dog-friendly Key West retreat. Featuring room for up to six guests and a cute canine companion (for a small nightly fee), street parking, a private hot tub, and a shared pool, your vacation promises to be one to remember. This home is nestled in a...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Cable/satellite TV
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tropical comfort abounds when you stay at this wonderful condo on the shores of Key West. Complete with a shared pool & hot tub, tennis courts, and a private, covered parking space, you'll have everything you need for an unforgettable Florida Keys escape. One dog is allowed for a small nightly fee....
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
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    • DVD Player
    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West home is waiting for you and your group of up to nine to come make yourselves at home and enjoy lazy days by your private pool. You'll be within easy reach of the beach, parks, and all the necessities. Walk to Higgs Beach and the pier, Indigenous Park, and dinner at Salute, then...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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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
    Sip a mug of coffee on the balcony as you take in views of the Florida sunrise at this superb Key West condo. Complete with luxurious amenities like a community pool and hot tub, a private parking space, and a dog-friendly policy, this wonderful vacation rental is sure to delight. The condo is...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cottage w/ shared pool, private hot tub, & street parking - Dogs OK!1 / 27
    (14)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 4, 2016
    This quaint villa was perfect for our party of 2 (might be a bit crowded for 4 adults, but for 2 kids it should be just fine!) The 1/1 was well appointed with everything we...
    Reviewed September 21, 2015
    We loved our stay here. It was decorated nicely, clean, and quiet. Housekeeping came in daily and did a good job. I liked the setup of the condo a lot; a nice, spacious...
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    About this property
    Treat yourself to a much-needed getaway filled with stress-free days and sun-soaked afternoons when you book your escape to this Key West retreat. Offering the chance to enjoy a private hot tub, street parking, a shared pool, and easy beach access, this home will make sure your stay is one to...
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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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    • Grill
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    • Hot Tub
    • Cable/satellite TV
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    • Parking
    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find the utmost in beauty and convenience at this two-bedroom Key West home, a light-filled escape with a private patio, a heated community pool, and an ideal location close to beaches, nightlife, restaurants, and historic sites. You'll find this elegant home in the Truman Annex neighborhood of...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Florida and stay in this private dog-friendly home for six for your Key West retreat and enjoy a private pool, wraparound deck, and patio. You'll be tucked away in a quiet Key West neighborhood, surrounded by lush foliage, and you'll be within walking distance of eateries, a market, and...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Ideal for a romantic getaway to Key West, this cozy, tropical-themed studio offers a shared swimming pool, outdoor seating and dining areas, a sun deck, and convenient access to exciting destinations like Duval Street, marinas, historic landmarks, and local beaches. The Garden House offers private,...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Charming, dog-friendly condo w/ balcony & full kitchen - great central location!1 / 27
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soak up the sun and kiss your stress away at this welcoming dog-friendly condo on Key West. The peace from the balcony will inspire your dreams for months to come! The central location makes for a convenient home base, whether your plans include a visit to the Butterfly Conservatory, The Hemingway...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 9, 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 January 19, 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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cute, dog-friendly condo w/ free shuttle, private patio, shared pool and hot tub1 / 24
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    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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    Lovely room in historic bed & breakfast w/ shared pool & a semi-private balcony1 / 24
    (1)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed February 3, 2016
    Clean, nice neighborhood. Lot's of Florida Key charm. Great location and close to Duvall street and far enough away to enjoy a quiet evening by the pool. Street parking can...
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    About this property
    Get the most out of your vacation days when you book this charming room at the historic Curry House Bed and Breakfast. With room for two and access to a shared pool, this vacation rental is perfect for a quick weekend getaway, a weeklong romantic retreat, and everything in between! When you stay...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Welcoming, budget-friendly studio w/ shared heated pool & home comforts1 / 25
    (1)Average
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed June 23, 2016
    If you stay here.. take your bags and lock the vehicle. I had my bag stolen from car as we took some bags to the room upon check in. Had to buy new clothes and lost cash and...
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    About this property
    See the best of Key West without breaking the bank when you book this cozy main-floor studio, which includes access to a shared heated pool and an unbeatable location in the heart of the city. Famous Duval Street - home to nightclubs, restaurants, stores, and more - is just two blocks away, as is...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore Key West with this conveniently located, dog-friendly condo as your home base! Duval Street's famous array of bars, shopping, and eateries is just outside your door. Explore the neighborhood's historic sights like the Ernest Hemingway House, about five blocks away. Stroll four blocks the...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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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
    Luxury and convenience combine in this recently renovated one-bedroom, one-bathroom condo in Key West. You'll love the shared pool, full kitchen, and various entertainment close to all the excitement of downtown! Sitting on the uppermost floor of a building surrounded by palm trees, you'll...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sunny tropical condo with a shared pool, close to all of the beachside action1 / 28
    (5)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • DVD Player
    • Cable/satellite TV
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    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 24, 2012
    Arrived with spouse and our 2 adult children. This condo was clean, had all the amenities that we could have hoped for. Nice quiet neighborhood, yet close to Duval St...
    Reviewed February 6, 2011
    Close to Duval St, and Mallory Square - within a 10 min walk with small kids. Amenities were great - kitchen, washer/dryer, family room. Access to pool. Looking forward to a...
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    About this property
    Boasting a great location in the Truman Annex, a shared pool, and easy beach access, you won't have to go far to dive into the beachside fun! Less than a mile to the picturesque Mallory Square and just under a mile to Fort Zachary Taylor Historic Park, there will be no shortage of attractions to...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue waters, warm winds, and the Florida sun await when you book a stay in this delightful two-bedroom condo with a private patio and heated community pool! Conveniently located just a few minutes from the Key West International Airport, this rental is part of the beautifully landscaped Sunset...
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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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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make those dreams of a beach getaway a reality and book your next Florida vacation at this luxurious Key West condo. With upscale resort amenities like a shared pool and hot tub, tennis courts, a fitness center, and a covered parking space, your vacation will be packed with tropical excitement from...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dog-friendly condo w/ scenic views, shared pool & hot tub, balcony & parking1 / 25
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 18, 2016
    My boyfriend and I checked in with another couple for a little under a week. The room was clean and was located within 5 miles of Duval Street. We all had a great time!
    Reviewed May 30, 2016
    We booked this with friends through trip advisor and really enjoyed our 1 night stay, rooms were spacious and comfortable with all mod cons and there was a great pool area.
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    About this property
    Pamper yourself with a stay in this luxurious and sunny Key West condo. Surrounded by beautiful tropical landscaping, and boasting resort amenities like a pool, hot tub, tennis courts and a private balcony with views of the Salt Ponds Preserve, this comfortable rental will have you relaxed and...
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    Location Information
    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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    • Parking
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
    • Grill
    • 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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    Spacious, dog-friendly rental w/ three hot tubs, near Duval Street and the beach1 / 49
    (2)Very good
    6 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    • Patio
    • Hot Tub
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 4, 2017
    This property is private and has the benefits of a kitchenette and a hot tub. Accommodations are very average--the room is no frills and could use updating and some new...
    Reviewed May 26, 2016
    Was a bit frustrated after arriving to realize the office that rents these was not on site but at 1075 duval suite 22..I had booked through booking. Com and at first they...
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    About this property
    Gather your group at this festive property, home to three private hot tubs, deck space, multiple kitchenettes, and six bedrooms for up to 24 people. The family dog is also welcome to join you for an additional nightly fee. You're about a block away from Southernmost Point, a photo-friendly...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 24
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    Studio condo w/ entertainment, full kitchen & private parking - central location1 / 21
    (27)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 13, 2015
    Loved this condo for our Keys getaway!! This place was perfect for our 5 day getaway and it's just 2 blocks from Duval. Very easy check in process took maybe 5 min at the most...
    Reviewed August 19, 2015
    We have stayed at Courtney's Place and another place farther down on Duval in the past. Hibiscus is closer to the "action" on Duval. Hibiscus is a unit for 2 people...
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    About this property
    Relaxation will come easy at this studio condo in Key West. With a calming interior, entertainment, and an awesome location with a private parking spot (with off-street parking) close to all the action, this getaway will be one to remember! Located in a historic building just one block from...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Grill
    • Patio
    • Air Conditioning
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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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    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Parking
    • Terrace
    • Patio
    • Internet Access
    • Grill
    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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Internet Access
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the tropical surroundings of Key West in style from the comfort of this dog-friendly condo! A shared pool, ocean views, and more await you. Nestled on the northern side of Key West, you have easy access to the shops and restaurants of Old Town, as well as a dock and the fresh ocean air of...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Family-friendly home w/ private pool, furnished patio, and parking - Dogs OK!1 / 24
    (14)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 9, 2014
    We were very happy with this house rental. The pictures only hold a small window into this gem. Walking distance to Duval (although a cab was only $6 if needed). Great living...
    Reviewed August 12, 2014
    Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking.Cons - across...
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    About this property
    Located right in the heart of Key West, this tastefully-appointed, tropical sanctuary comes with a private swimming pool, enclosed yard, and room for up to six guests. The family dog is also welcome to join you for an additional nightly fee. Take a stroll down to Duval Street and enjoy the many...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spacious main-floor suite w/ private patio & easy access to shared heated pool!1 / 9
    (1)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 2016
    Very private room with a nice patio, only steps away from the pool, which unfortunately we didn't get to use much as there was some kind of work being done in the pool area...
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    About this property
    One of the most in-demand rooms at the Garden House Bed & Breakfast, the Royal Poinciana feels secluded thanks to its private patio and its quiet location at the end of the house. It's perfect for a couple on a romantic retreat or a solo traveler hoping to enjoy some peace and solitude on their Key...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 11, 2016
    Depending on your agenda while on the Rock, this place should be perfect for you! I'll definitely stay here again!
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    About this property
    Vacation in the heart of Key West when you stay at the beautiful Garden House Bed & Breakfast. With room for two, a private bathroom, and access to a shared heated pool, this charming suite is a dream come true for a couple seeking a romantic retreat or a solo traveler who wants to see the best of...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Internet Access
    • Balcony
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your loved ones deserve to rest and relax under some Florida sunshine. Give them the vacation they deserve with this dog-friendly Key West condo with shared amenities like a pool and a hot tub. Courtesy Shuttle available to condo from airport and ferry terminal. A private parking spot is...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 16, 2016
    Sandy and her team at Curry House are friendly, helpful and welcome you to the B & B with a warm smile and they give you a hug when you leave. I went with my partner and our...
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    About this property
    A fun-filled Key West getaway for two starts with this lovely room in the historic Curry House Bed & Breakfast. Cozy and comfortable, the room includes access to a shared pool as well as a semi-private balcony, which faces the street toward the front of the home. Curry House is located in a quiet...
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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
    • Internet Access
    • Hot Tub
    • Grill
    • Cable/satellite TV
    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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Balcony
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy and compact, this recently renovated attic room in the historic Curry House Bed & Breakfast is perfect for two guests traveling on a budget. This room includes access to the shared backyard pool, air conditioning, and typical home comforts - everything you need for the vacation of a lifetime....
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Parking
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Affectionately known as the Captain’s Quarters, this two-story custom-built 3BR/3BA is located on a quiet lane in Bahama Village. This lovely neighborhood exudes a charming old Key West vibe. Please inquire for options. Step out to your back yard for a dip in the private pool, set amid lush...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Key West paradise with shared pool - close to shops, restaurants, and beaches1 / 30
    (1)Terrible
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Air Conditioning
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for a romantic getaway or a small family vacation for four, this adorable Key West studio with side-by-side beds offers a shared, heated pool, outdoor seating and dining areas, and a well-maintained courtyard. This home also offers private parking for an additional fee. Just a couple of...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Grill
    • Washer
    • Parking
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 13, 2015
    Well, talk about HIGH season. Prices are dear and the lines of cars down the highway get longer each day between Xmas and New Year's. But Key West is a special place, at least...
    Reviewed December 23, 2014
    Stayed for a week before Christmas 2014. I did a bit of research on different properties/hotels, and really wanted to get away from the traditional 'resort' style...
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    About this property
    Absolutely ideal for a romantic getaway for two, this cozy studio offers a well-equipped kitchenette, a furnished deck, and access to a shared swimming pool at the heart of a beautifully-maintained tropical courtyard. Located just a block from Duval Street, the hottest street in Key West,...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Parking
    • Washer
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 1, 2017
    Yes, it's located 2-3 blocks South of Duval Street, nearer the Southern-most point end, and it was walkable to everywhere for us, and better on bikes, but I just couldn't get...
    Reviewed October 7, 2014
    The place was pretty decent overall however it is not in the safest feeling part of town. We learned that it is right next to public housing and there are some loud neighbors...
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    About this property
    This dog-friendly Key West gem offers a palm-covered patio and grill area, a kitchenette, free WiFi, and street parking! Plus, you're walking distance from the beach, historic landmarks, and local dining. Walk a half mile to the beach and enjoy Key West's legendary white sand and turquoise water!...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're planning a Key West vacation for yourself or your sweetheart, you can't go wrong with this charming suite in the heart of the city. Whether you're lounging by the shared pool, soaking up the sun on the semi-secluded second-floor sun deck, or relaxing in your room, you're sure to enjoy...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience Key West from the comfort of this cozy beach suite, complete with a kitchenette, private bathroom, and sleeping space for two. Your convenient location in the heart of Old Town makes this a wonderful couple's getaway! Walk over to Zachary Taylor State Park and Beach for glimpses of...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Condo in historic district w/shared hot tub  - 2 blocks to ocean, dogs OK1 / 28
    (24)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Grill
    • Cable/satellite TV
    • Washer
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 22, 2015
    We just spent a week at SMR and really enjoyed our stay!Close to duval without the noise! We could hear some live music from la te da one night, but it was nice to sit on the...
    Reviewed November 23, 2014
    Location right on Duval was awesome! We were close to everything! The condo has a great layout. Fully functional kitchen. 2 bedrooms with TVs. Outdoor space with hot tub...
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    About this property
    Here in the heart of historic Key West, you'll have access to a shared hot tub, dog-friendly accommodations, and grill on your backyard patio area, as well as private parking! From here, you're only two blocks from the beach at Fort Zachary Taylor State Park. Duval Street's restaurants, bars, and...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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