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Sugarloaf Key Apartment Rentals

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    Travellers to Sugarloaf Key are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    49 Matching Rentals in Sugarloaf KeyView all 207 rentals
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    Cozy, dog-friendly cottage w/ patio - walk to shops, restaurants, and more!1 / 26
    (29)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Romantic & elegant studio-style cottage w/ private hot tub - dog-friendly!1 / 26
    (3)Very good
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    Reviewed 16 May 2016
    As far as the accommodation is concerned, the location is unsurpassed. The cottage is clean, comfortable and well appointed. Sadly what let's the place down are the...
    Reviewed 11 November 2015
    This is the second time we've stayed in this rental complex. The first time upstairs and now this time in the back. The location off of Whitehead is perfect for everything we...
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    About this property
    Experience the best of Key West from the comfort of this charming studio-style cottage. A private hot tub, dog-friendly accommodations, and modern conveniences including free WiFi and a shared washer/dryer make this vacation rental perfect for everything from a laid-back retreat to an...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio condo w/ entertainment, full kitchen & private parking - central location1 / 21
    (27)Very good
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    Pet friendly
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    Reviewed 13 October 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 19 August 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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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Pet friendly
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    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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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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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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    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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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Pet friendly
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    Smoking allowed
    About this property
    Plan your romantic getaway to this beach condo steps away from Key West's famous beaches, restaurants, and landmarks! The Salvador Dali Suite offers a central location and dog-friendly accommodations. You're situated in the heart of town, so local eateries like Banana Cafe, about a quarter-mile...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Upper-floor suite in historic home w/ shared on-site pool & semi-private veranda1 / 24
    (1)Excellent
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    • Air Conditioning
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    Arrived and all paperwork was ready, easy to communicate thru emails and even phone calls, great customer service. Place was quaint and cute, felt comfortable and safe. Room...
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    About this property
    If you're planning a romantic Key West vacation for you and your sweetheart, this charming Curry House suite might be just what you're looking for! Up to two guests will enjoy lounging by the shared on-site pool, people-watching on the semi-private veranda, and relaxing in the shared sitting rooms...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    About this property
    This beautiful main-floor suite is the largest room in the historic Garden House Bed & Breakfast and features a semi-private porch, access to the shared pool, and a desk, making it ideal for a traveling couple or a writer's retreat. The Garden House sits just a few blocks away from both Duval...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Cozy studio condo w/ shared pool & courtyard - easy beach access! Dogs OK!1 / 27
    (2)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2016
    Loved the stay here. Close to Duvall. Could walk to anywhere on the island including historical sites, any restaurant. Centrally located. Rooms very clean and spacious. Only...
    Reviewed 11 November 2014
    This place was perfect for what we were looking for:Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
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    About this property
    Let time wash over you in gentle waves while you relax in the sunny paradise of Key West at this cozy studio condo, offering access to a shared pool, courtyard, and an easy walk to the soft sandy beach. Located in the heart of downtown Key West as part of the larger Banana Foster's Guest House,...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Tropical Key West studio w/ shared pool - near beaches & Duval St.1 / 24
    (8)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2015
    Clean, quiet, beautiful garden pool, well managed, prompt shuttle, fun to watch the iguanas marching thru and sun bathing in the palm trees. Locations is great, close to Duval...
    Reviewed 30 July 2014
    Papa's Hideaway is located on a quiet side street, a block away fromKey West's main drag, Duval Street, and a two-block walk from the"Southernmost Point" landmark: a...
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    About this property
    Plan a romantic getaway for two to Key West at this quaint studio rental complete with a well-equipped kitchenette, furnished patio, and access to a shared swimming pool, well-maintained tropical courtyard, and sundeck. This complex is located in a quiet, residential neighborhood and there is...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Cozy tropical suite w/ patio and half a mile from the beach - dog OK1 / 23
    (8)Average
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 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 7 October 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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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    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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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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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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    About this property
    Experience a piece of Key West's past when you book a stay at this charming ground-floor suite in the historic Curry House Bed & Breakfast! Up to two guests will enjoy a shared on-site pool, home comforts, and a convenient location in the heart of the city. Curry House sits three blocks off of...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Welcoming, budget-friendly studio w/ shared heated pool & home comforts1 / 25
    (1)Average
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    Pet friendly
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    Smoking allowed
    Reviewed 23 June 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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    Cozy, dog-friendly suite w/ shared hot tubs, grill, and patio space to relax1 / 27
    (3)Excellent
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 March 2016
    My Daughter and I stayed in Ibis Suite.We Loved the location and the secluded quietness of our suite.The Cuban coffee shop, the Sandwich shop, the Grocery store, the Trolley...
    Reviewed 2 June 2015
    My friends and I stayed at Ibis this past January (all in our mid 20's). I thought I reviewed this property then, but apparently I did not. It was our first trip to Key West and...
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    About this property
    Ibis Suite offers visitors a prime location in Old Town Key West, great amenities, and space to relax. Top off your visit with soaking time in one of the property's hot tubs, and you're well on your way to an optimal Key West experience. Here, you're a few blocks off of famous Duval Street, home...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Pet friendly
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    Smoking allowed
    About this property
    Kick your shoes off and relax in paradise at the farthest end of Key West at this adorable upper-level studio rental, complete with a plush bed and writing desk as well as a well-maintained courtyard with a shared swimming pool, outdoor seating and dining areas, and a sun deck. This second-floor...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Cozy, dog-friendly retreat w/ shared hot tubs, patio, great location in Old Town1 / 29
    (2)Excellent
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    Pet friendly
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    Smoking allowed
    Reviewed 25 June 2015
    This place was perfect for our vacation needs. It was close to everything, and the places a bit further away totally doable by renting bikes for the week. We cooked some meals...
    Reviewed 28 August 2014
    This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin...
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    About this property
    Take a break from the ordinary with a visit to this tropical hideaway in the heart of Key West's historic district! Ideal for a romantic getaway, this suite promises comfort, space to relax, and a prime location in Old Town. The family dog is also welcome to join you for an additional nightly fee....
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Dog-friendly studio w/ private deck & hot tub - 1 block to Duval St!1 / 27
    (4)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2014
    We rented three units for 5 nites. We had a great week. The staff was very friendy. Everything was clean, Couldn't have ask for a better place to spend our vacation. Cant wait...
    Reviewed 29 July 2014
    From the minute we stepped off the plane, we were extremely impressed by Key West Vacation Rentals. We flew in on a Saturday morning, and they do not typically do airport...
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    About this property
    Spend your Key West vacation days relaxing in your private hot tub and strolling along Duval Street when you stay at this lovely second-floor studio with dog-friendly accommodations. This vacation rental's location is perfect for taking in Key West culture. Located just one block away from Duval...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Deluxe, ground-floor studio w/ view of the courtyard and pool - close to shops1 / 23
    (14)Very good
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    Pet friendly
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    Smoking allowed
    Reviewed 19 September 2015
    The setting is very secluded yet only two blocks from Duval Street. The main house is very nice with 2 bedrooms, 2 baths, kitchen, dining and living room. A porch surrounds 3...
    Reviewed 4 June 2015
    By far the best part about our stay was the pool. It was so great to have somewhere to relax while we were in Key West. That's the whole point in going! The pool was the perfect...
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    About this property
    Enjoy that next romantic getaway in Key West at this adorable and colorful ground-floor studio complete with a well-equipped kitchenette and view of the well-maintained courtyard and shared heated pool. Please note that off-street parking is available at this address. Take a short stroll over to...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Cute, dog-friendly condo w/ shared hot tub in the heart of historic Key West!1 / 25
    (2)Very good
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2014
    The room was a nice size for two friends. It was not fancy, but clean and well equipped. Another plus was the front porch where we sat and people watched while having coffee or...
    Reviewed 25 July 2014
    The Egret Studio is very close to the Southernmost Point and next door to a Cuban cafe, so I had coffee there every morning. The studio is very clean, well appointed and we...
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    About this property
    Settle in at this conveniently located four-person suite, where you'll have access to a shared hot tub and your own kitchenette! Egret Suite can be rented on its own, or as a part of the entire property for larger groups. The family dog is also welcome to join you for an additional nightly fee. At...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    About this property
    Your island escape will be worth dreaming about when you stay at this affordable studio in central Key West. With a shared balcony for relaxing among the palm trees, dog-friendly accommodations, and beach access nearby, you'll be basking in paradise every second you're here! Located on Duval...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience life at the top - the top floor of Curry House Bed & Breakfast, that is! Up to two guests will love staying in this cozy room, which offers a birds-eye view of Key West, access to a shared backyard pool, air conditioning, and more! Curry House sits just three blocks from both bustling...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Charming studio w/ shared pool, covered patio - a block from shopping and dining1 / 27
    (8)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 January 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 23 December 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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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Pet friendly
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    Smoking allowed
    About this property
    Looking for a budget-friendly Key West getaway? Consider this cozy room in the Garden House Bed & Breakfast! Great for a couple's retreat or a solo adventure, guests of this room will enjoy a great location, a shared pool, and modern home conveniences. The Garden House Bed & Breakfast sits in the...
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    Sugarloaf Key, Florida Keys 33040
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    About this property
    If you're looking for a budget-friendly home base and plan to spend most of your time enjoying the waves and exploring, this efficient studio is just the ticket. You and one other traveling companion will be in a prime location, within walking distance to the beach and Key West major attractions....
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    About this property
    Tucked away in the trees, this Key West hideaway is a great choice for couples or small families. Shared hot tub access and patio space will have you feeling right at home in Pelican Suite! Take a walk a couple blocks down and you're at the beach, toes in the sand. Local staple Louie's Backyard...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 2014
    Located right by the Southernmost Hotel and a block off Duval this was a great stepping off point for fun in Key West. Cuban market on the corner for café con leche each...
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    About this property
    Heron Suite's hot tubs access, back patio space, and proximity to the beach set the tone for a lovely stay in Key West's historic district! Well-outfitted for a couple's getaway, this suite offers an excellent location paired with the amenities of home. The family dog is also welcome to join you...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Quaint studio comfort with shared pool and sun deck - walk into town1 / 31
    (2)Very good
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    Pet friendly
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    Smoking allowed
    Reviewed 28 July 2014
    Our stay at Paradise Palms was truly a month in paradise. The house was just the right size with new interior and appliances. The location is in a nice neighborhood that was a...
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    About this property
    Experience the southernmost point of Key West at this absolutely charming, nautical-themed studio rental for two with access to a shared pool, well-maintained courtyard, and sun deck. Private parking is available for a small fee. This home is just a couple blocks away from Duval Street, perhaps...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Pet friendly
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    Smoking allowed
    About this property
    Spend your vacation days in comfort when you stay at the charming Garden House Bed & Breakfast. This ground-floor suite is perfect for one or two travelers and includes access to the shared heated pool as well as plenty of home comforts. Garden House is just a few minutes away from Duval Street,...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Dog-friendly beach suite w/ shared hot tubs, kitchenette, patio space, and more!1 / 29
    (6)Average
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 April 2017
    We stayed from Monday through Thursday so we expected lower crowds but were we surprised. Check in was easy but at a different location. It was a surprise to have to park our...
    Reviewed 12 December 2015
    First impression was that room smelled clean. Very secluded and minutes from Duval Street. Second night, noticed a lot of critter activity. Small bugs and roaches. Management...
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    About this property
    Look no further than this homey suite for your next couple's weekend! Take a dip in the property's shared hot tubs, or simply enjoy the fresh air on the patio space outside your doorstep. Seagull Suite situates you walking distance from historic Duval Street's attractions, from dining like Blue...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Spacious main-floor suite w/ private patio & easy access to shared heated pool!1 / 9
    (1)Very good
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    • Patio
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    Pet friendly
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    Smoking allowed
    Reviewed 14 September 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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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    • Internet Access
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    • Terrace
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the glorious waves and sunshine of Key West at this second-floor studio, featuring a shared pool, one private parking spot, and close proximity to the beach, restaurants, and more! This studio is part of Banana's Foster Guest House, which can accommodate a much larger group. Located on the...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    • Air Conditioning
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a piece of Key West history when you rent this charming Curry House suite, which features a private en suite bathroom, a semi-private balcony, a shared pool, and room for up to two guests! Located in a quiet neighborhood three blocks from Duval Street, Curry House is peaceful and...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Cozy, dog-friendly condo with views - walk to beach, dining, & attractions1 / 33
    (6)Average
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 December 2016
    Walking distance to restaurants and attractions. The room was clean and well appointed. Location was very private. Check in and out was easy and within walking distance. 4...
    Reviewed 14 July 2014
    Coral Cove was a great place to stay for 2 people. We only stayed for one night, which was just enough. It was a little cramped, but was a safe and comfortable place to sleep...
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    About this property
    Escape to Key West for a romantic getaway for two and walk to the beach, dining, and other attractions when you make this cozy, efficiency studio yours. You'll be located in a quiet neighborhood and surrounded by tropical vegetation and decking for great views. You'll be within walking distance to...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Ground-floor studio w/ shared heated pool - walking distance to everything!1 / 25
    (1)Very good
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 June 2016
    Although the room I stayed in (The Gecko Grotto-Garden House) was a tad bit small it was quite cozy and welcoming. The description said that there would be a microwave and...
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    About this property
    You and your loved one will be close to the action when you stay at this charming two-person suite in the historic Garden House Bed & Breakfast. Whether you're strolling the streets of Key West, relaxing in the comfort of your spacious room, or lounging by the shared heated pool, you're sure to...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    • Internet Access
    • Terrace
    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Planning a romantic getaway to Key West? Consider this spacious main-floor suite! Part of the historic Curry House Bed & Breakfast, the suite includes access to a shared pool and home conveniences. Curry House sits in a quiet neighborhood but is just a few blocks away from the shops, restaurants,...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Charming tropical getaway w/ shared pool, sundeck, and bar - near Duval Street1 / 24
    (4)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Balcony
    • Parking
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    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 November 2014
    Papa's Hideaway is a hidden paradise! It is beautiful and comfortable and close to everything. The bed was extremely comfortable and furnished with everything we needed for a...
    Reviewed 18 March 2014
    Loved the location to everything,walking distance and even had parking included in the cost of rental...made me feel relaxed instantly,loved hanging out at the pool and meeting...
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    About this property
    This second-floor studio has a private outdoor seating area and plenty of space for up to four guests. Spend time at home splashing in the shared pool or catch some rays on the sundeck. Located in a residential neighborhood, this rental is just a short walk from Duval Street for the area's best...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Enjoy a shared pool & a great location at this main-floor bed & breakfast suite!1 / 30
    (1)Excellent
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    Reviewed 11 May 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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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Spacious room in historic Curry House - shared pool & semi-private front balcony1 / 28
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 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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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Searching for an affordable long-term vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Tune into the Windchime! This lovely studio for two comes with all the comforts you need for an extended stay away from home, along with a...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Lovely room in historic bed & breakfast w/ shared pool & a semi-private balcony1 / 24
    (1)Very good
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 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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    Cute, dog-friendly cottage w/ patio - walk to shops, restaurants & nightlife!1 / 30
    (31)Very good
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2015
    This rental company is one of the best - I've had numerous occasion to use their services. We arrived very early, but were allowed to park our car at the rental location and...
    Reviewed 17 November 2014
    We had a great stay and will for sure be staying in one of these cottages again. Great location close to nice restaurants approx midway Duval and North 2 blocks. Stayed for a...
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    About this property
    Enjoy one of the most desirable locations in Key West at this studio-style cottage, where you'll have an outdoor patio, dog-friendly accommodations, and wonderful access to beaches, restaurants, and shops! This cottage is part of the Simonton Court complex, which is within walking distance of the...
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    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    other traveller has booked this property
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    Pet friendly
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    About this property
    Pack your bags and leave your worries behind for an exciting trip to Key West! This studio has everything you need to have a great time, including access to a shared pool, an outdoor dining area, and nearby beach access for endless sunny days. Part of the larger Banana's Foster Guest House, this...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    • Balcony
    • Terrace
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best of Key West is at your fingertips with this charming two-person suite, which includes a shared backyard pool, a semi-private veranda with rooftop views of the city, and typical home conveniences, making it perfect for a traveling couple or a solo adventurer. This room is part of the...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio condo w/ shared courtyard & pool - walk to everything - dogs welcome!1 / 29
    (1)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2016
    If you're looking for an affordable place to crash at the end of a few crazy Key West days and nights, this is perfect. Terrific location, right at the intersection of Simonton...
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    About this property
    Bask in tropical sunshine and waves in the paradise of Key West for your next vacation with this cozy studio. Featuring a kitchenette, shared pool, and courtyard in an awesome central location, two guests will feel right at home here. The family dog is also welcome here for an additional nightly...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Charming, dog-friendly home in a residential neighborhood w/ shared pool1 / 29
    (8)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.This is what my (now) husband and I used during our stay.It was...
    Reviewed 3 April 2016
    This place was very private, tropical, had a very nice pool with about 5 or 6 apartment/houses surrounding the pool that you hardly knew were there. They were hidden with...
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    About this property
    If you're looking for the perfect romantic escape for your next getaway, then look no further than this romantic Key West cottage. Featuring room for two guests to enjoy a shared pool and a location that puts you within easy reach of all of the local attractions, this is the perfect spot for a...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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