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Vacation Rentals nearby The Ernest Hemingway Home and Museum

907 Whitehead Street, Key West, Florida 33040-7473
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    Travellers to Key West are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Shelleys Rooftop Hideaway1 / 15
    (7)Excellent
    0.2 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH1 / 61
    (8)Excellent
    0.3 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!1 / 25
    (17)Very good
    0.1 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok1 / 28
    (2)Very good
    0.1 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 15, 2018
    We were very pleased to locate this little home with a shared pool in the heart of the historic district. We were a group of 4 so we were looking for a clean, comfortable, and...
    Reviewed March 7, 2017
    Clean, quaint, and comfortable. The office help was great, and cleaning service was good. This is close to all of the action while maintaining a peaceful night's sleep.
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    About this property
    Up to four guests can enjoy all the fun of Key West at this updated home complete with a shared pool with waterfall, and lush, outdoor seating area. As an added bonus, this home comes with private, off-street parking for one vehicle - a real luxury in the Keys! Dogs are allowed for a small nightly...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.1 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this beautifully remodeled home with quaint charm and colorful front and back porches. Take in the lush landscaping that surrounds the one-of-a-kind lazy river heated pool, or relax in the well-designed interior. This home features Key West flair, two workstations, two bicycles, ceiling fans,...
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    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool1 / 29
    (5)Very good
    0.3 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Private Garden
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 1, 2018
    Just one building off of Duval so you are literally steps from the action and all the conveniences that Duval offers. Yet, the house it located on a short dead-end alley...
    Reviewed October 13, 2014
    The Bahama House looked just like the pictures and the location was just as advertised-convenient!! The staff at Key West Rentals were quick to respond to issues with pool and...
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    About this property
    Privacy meets convenience at this beautiful Key West vacation rental, which features a two-bedroom, two-bathroom home, a separate studio cottage, a private pool, and room for up to eight guests. The family dog is also welcome to join you for an additional nightly fee. This recently renovated...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Couple's dog-friendly getaway with central location and access to a shared pool1 / 26
    (39)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 4, 2015
    I cannot say enough great things about this place. There are 6 duplexes totaling 12 2 story cottages. In the center of all the cottages is a communal area considering of a...
    Reviewed February 28, 2015
    The pictures of the Bermuda Suite are better than the reality, but it is not bad. It is in a gated courtyard complex and the location is ideal. We were able to walk everywhere...
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    About this property
    Book your romantic escape to this dog-friendly Key West home. With access to a shared pool and a great location on Duval Street, you'll be able to slip into vacation mode in no time. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am This home is just a block from the...
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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Two-level dog-friendly cottage w/shared pool, outdoor shower - near the beach1 / 33
    (20)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2015
    This is our second year at this location. This year we chose the Havana Suite. The unit was extremely clean and pleasantly decorated. Very nice kitchen. TVs in the bedroom and...
    Reviewed April 27, 2015
    We chose Little Havana initially because of the location. It is a smidgen off the beaten path from the hustle and bustle of the Duval action, yet within walking distance to a...
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    About this property
    Slip into vacation mode at this dog-friendly Key West cottage. Featuring room for up to four people, two levels, a shared pool, and easy access to all of the seaside action, this home promises to make your next vacation fun-filled and hassle-free! Notice: This is in a residential area, Quiet...
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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Dog-friendly, colorful cottages w/ pool & hot tub in a fabulous location!1 / 44
    (14)Excellent
    0.0 kilometres from The Ernest Hemingway Home and Museum
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Washer
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 1, 2015
    Three generations, nine people, stayed here over Christmas. We each had space to be by ourselves, and we all had space to get together. Nine of us sat around the table in the...
    Reviewed September 3, 2014
    I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
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    About this property
    A large group getaway to Key West starts with this pair of charming cottages, which feature a total five bedrooms, three-and-a-half bathrooms, and a max occupancy of 16. The property also includes a private heated swimming pool, a private hot tub, and dog-friendly accommodations. The cottages...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    0.2 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take your romantic getaway at this bright studio condo in the heart of Key West's historic Old Town! Free WiFi, a deck, and a kitchenette will have you feeling right at home less than a mile from the beach. Visit Fort Zachary Taylor State Park & Beach, about a mile away, where you'll find white...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Comfortable condo living w/ shared pool & lush gardens - in Old Town, dogs ok1 / 25
    (21)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Terrace
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 29, 2015
    The location is perfect, almost in the middle of it all. Downstairs are nice restaurants. If you don’t want to cook, go to NY Pasta Garden down stairs. They serve a fantastic...
    Reviewed September 13, 2015
    The check in process for KWVR was fast and easy. The office staff is very friendly and helpful. We found Casa Bonita spacious for the four of us and our dog. The kitchen is...
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    About this property
    Experience all that Old Town Key West has to offer at this beautiful, roomy condo located right off Duval Street. Featuring a large, shared swimming pool, lush, tropical gardens, private, covered parking, and space for up to six lucky guests, this vacation rental is ready-made for a fun, family...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.3 kilometres from The Ernest Hemingway Home and Museum
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in style in the heart of Key West's historic downtown, where you're steps from the beach and all Duval Street has to offer! Your back patio houses a private hot tub, dog-friendly accommodations, and grill, perfect for lounging with the group after a long day of play. You're located on...
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    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Deluxe, ground-floor studio w/ view of the courtyard and pool - close to shops1 / 23
    (14)Very good
    0.3 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 19, 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 June 4, 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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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    0.3 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    Suitability
    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...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    0.2 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the unbeatable location of this Key West studio. A ceiling fan and window unit A/C helps keep the Florida heat at bay, while the shared courtyard and covered porches are a great place to enjoy the evenings. What's nearby: This cozy studio apartment is located in a quiet neighborhood with...
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    Location Information
    Stock Island, Florida Keys
    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
    0.3 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.1 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If Key West is on your travel itinerary, make this lovely rental for six your home away from home and spend your time lounging by your private pool and spa. Located in Historic Bahama Village, this home is one block away from the world-famous Duval Street, where you can enjoy galleries, shops,...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Romantic & elegant studio-style cottage w/ private hot tub - dog-friendly!1 / 26
    (3)Very good
    0.1 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 16, 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 November 11, 2015
    This is the second time we've stayed in this rental complex. The first time upstairs and now this time in the back. The location off of Whitehead is perfect for everything we...
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    About this property
    Experience the best of Key West from the comfort of this charming studio-style cottage. A private hot tub, dog-friendly accommodations, and modern conveniences including free WiFi and a shared washer/dryer make this vacation rental perfect for everything from a laid-back retreat to an...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.3 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Balcony
    • Washer
    • Terrace
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to paradise at this family-friendly, three-bedroom Key West townhouse with a full, modern kitchen, furnished deck, and a shared on-site pool - all close to shops, beaches, and local attractions. This townhouse is within walking distance of many of Key West's most popular destinations,...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Stunning home near beach and town with private hot tub and shared pool - dogs OK1 / 21
    (5)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 12, 2014
    We were at Tobago House for the month of February 2014. It is absolutely wonderful !! I will say that I would have preferred if everything had been tested out before we got...
    Reviewed January 23, 2014
    Tobago House is very nice, close to Duval - quiet street.Nice amenities, pool, hot tub, great outdoor area. Would recommend to anyone. Close walk to everything.Wonderful!
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    About this property
    Make your next stay in the Florida Keys one to remember with this amazing home in Key West! Two bedrooms, two bathrooms, dog-friendly accommodations, and a shared pool ensure your next trip to the tropics will be one you'll always remember. Your home is only a block away from the famous shops...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.1 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to Key West for a sun-filled getaway and stay in this lovely two-bedroom retreat with a private pool for an unforgettable reprieve from life's hectic pace. Bring the dog along for a small nightly fee and revel in your close proximity to famous Duval Street and more! You'll be situated in...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok1 / 33
    (50)Very good
    0.3 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 16, 2014
    The rental is great and in an excellent location. We had a group of 6 and had no issues. Note: unlike some rentals there is nothing in the house if you plan to cook. You...
    Reviewed July 24, 2014
    Everything was easy and perfect check in wise. Rooms were clean. Will stay here again. Walked to all bars and loved the tall ceilings.
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    About this property
    Immerse yourself in the island lifestyle when you book this Key West accommodation, comprised of a two-bedroom house and a separate one-bedroom pool house. Featuring a private heated pool, a private parking spot, and an outdoor shower, this home gives you the chance to unwind. Four dogs are...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Cozy, dog-friendly cottage w/ patio - walk to shops, restaurants, and more!1 / 25
    (29)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 14, 2016
    Beautiful room, stocked kitchen, comfortable bed, private front porch. Loved everything about it! We only stayed one night but we could have stayed a month!
    Reviewed July 13, 2015
    Can't say enough about this place. Will never stay at another location in Key West. Staff was kind and helpful. Felt like this place was my own home, very cozy. Highly recommend.
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    About this property
    Enjoy the tropical ambience of this studio-style Key West cottage, where you'll find a private patio, dog-friendly accommodations, and a perfect location for dining, shopping, and exploring the local beaches and nightlife. This sweet yellow cottage is located in a small complex that sits within...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    A Key West gem w/ a private pool - close to shops & restaurants, dog-friendly1 / 26
    (13)Very good
    0.3 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 11, 2017
    We visit Key West every couple years and stay in a different rental house each trip. This time we chose Helen's Hideaway, because A) it is a minute walk to Duval Street and B...
    Reviewed June 6, 2016
    Absolutely loved the place. We were a group of 5 girls and we found the villa really comfortable, spacious, clean and well stocked with towels, toiletries and kitchen...
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    About this property
    Escape to Key West with the family at this charming Floridian home on a quiet street with a furnished patio, private, heated swimming pool, and space for up to six guests and a dog for a small nightly fee. This home also offers off-street, private parking for one vehicle. Located alongside...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Colorful, dog-friendly cottage w/ private pool & all the comforts of home1 / 30
    (8)Very good
    0.0 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Private Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2016
    The management staff were very friendly. The house is right on Truman st. A couple of feet from Duval St. House as pictured in ad. We were a total of 8 people 5 adults and 3...
    Reviewed July 25, 2014
    This is our second time staying in this property. We stayed here again because the property manager & his team were fantastic, the property was very clean and it was a...
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    About this property
    Experience a quintessential Key West vacation when you stay at this historic three-bedroom, two-and-a-half-bathroom cottage. With a private heated pool, home comforts including free WiFi and cable TV, and room for up to eight guests, this home is perfect for a large family or a group of close...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Historic vacation rental with a private pool - dog-friendly!1 / 25
    (3)Average
    0.1 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 15, 2015
    My husband and I stayed here with 2 other couples. The location was absolutely perfect for walking or biking to anywhere on the island. The pool and outdoor area were also...
    Reviewed July 29, 2014
    This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management...
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    About this property
    A sun-soaked getaway in the Florida Keys awaits you when you stay at this beautiful dog-friendly vacation rental! Lounge in comfort by the private pool or stay inside and enjoy the air conditioning while you browse the cable channels on the flatscreen TV. However you spend your vacation days,...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Island condo w/ balcony & great central location - beach nearby! Dogs OK!1 / 25
    (42)Very good
    0.3 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 17, 2016
    Not even a block off Duval near the Southernmost end of the island (i.e., the quiet end of Duval), this efficiency was a great find. Located in a renovated old house with...
    Reviewed November 10, 2016
    The location is great. Right next to duval street. But it's definitely too small even for 4 persons.... we were walking in each other. One fan wasn't working and in the kitchen...
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    About this property
    This one-bedroom, one-bathroom condo in Key West, featuring entertainment, a wrap-around balcony, and beach access nearby! The family dog is also welcome to join you for an additional nightly fee. Located on the corner of Duval Street and Amelia Street, you'll be close to all the excitement...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.1 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Suprise your special someone with a stay at this charming and colorful Key West retreat! Set right in the heart of downtown, this home offers the perfect opportunity to enjoy a sun-kissed vacation you'll never forget. Located steps from the intersection of Truman Avenue and Whitehead Street,...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.1 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the tropics of Key West at this dog-friendly cottage with a private heated pool and a lush backyard garden. This lovely cottage is located in Old Town near Duval Street, minutes from restaurants, museums, and the daily sunset celebration at Mallory Square. Stay cool with air...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Dog-friendly studio w/ private deck & hot tub - 1 block to Duval St!1 / 27
    (4)Very good
    0.1 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 12, 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 July 29, 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...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    0.0 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Grill
    • Patio
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This turn-of-the-century Key West vacation rental is ready and waiting to be your home away from home for your next family getaway. Spacious enough for up to eight guests and a dog (for a small nightly fee), this home comes with a tropically-landscaped back yard and a private, outdoor hot tub. This...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.2 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in style during your visit to Key West - this home offers a private parking spot, an upstairs deck, dog-friendly accommodations, and plenty of space for your group to relax. Enjoy a full kitchen, free WiFi, and a pull-out bed at Duval Delight. At this home, you're on the end of historic...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Classic Key West cottage featuring shared pool, courtyard, covered front porch1 / 27
    (17)Very good
    0.3 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 27, 2017
    We stayed here after having a rough go of it in Miami and we fell in love. My kids said "Mom we should have stayed here the whole time, this place is awesome." The pool...
    Reviewed September 10, 2015
    Beautifully decorated Old Key West home. Our kids (12, 5) loved seeing the Iguana in the courtyard. The pool was nice to relax in after a day of sightseeing. Beds were...
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    About this property
    Part of the Papa's Hideaway complex, this charming, old Key West cottage is an ideal home away from home for that next vacation to the Southernmost Point. Up to six guests can enjoy this recently updated home complete with a high-end kitchen, loads of modern amenities, a shared swimming pool,...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Historic, dog-friendly cottage in the heart of Key West w/ private hot tub1 / 27
    (16)Very good
    0.0 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 28, 2016
    This house had a wonderful location. It was very easy to walk to Duval Street and the Southernmost Point. The beds were comfortable, but the house inside and out needs...
    Reviewed July 1, 2014
    Our first visit to the Keys celebrating our 28th anniversary with our adult children, (3 couples) this historic cottage slept all 6 of us very comfortably; in fact, the most...
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    About this property
    If you're looking for a convenient home base for your Key West adventure, consider this two-bedroom, one-bathroom vacation rental. Up to six guests will enjoy the convenient location, a private hot tub, a fully equipped kitchen, and more! The family dog is also welcome to join you for an additional...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Dog-friendly condo w/ porch & Old Town location - walk to beaches & restaurants!1 / 26
    (25)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 22, 2017
    Great adult week 1 block away from Duval street. the house was very clean! we had the best time ever!!!
    Reviewed February 7, 2015
    For $1700 for 5 nights, I expected a little more. First, I considered doing laundry on the last day, but the dryer door doesn't close (as evidenced by the tape marks all over it...
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    About this property
    Enjoy one of the most enviable locations in Key West when you escape to this two-bedroom condo, where you'll have a dog-friendly interior, a private covered porch, and wonderful access to beaches, restaurants, and the Old Town. This gated property sits in the heart of Old Town Key West, just one...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.0 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    • Air Conditioning
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring some sunshine and fresh ocean air into your next romantic getaway with this cozy Key West home. You'll enjoy a great location right at the center of the action, with a uniquely decorated and vibrant atmosphere awaiting you back at home! Right off Truman Avenue, this condo for two lies...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.3 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this stylish, three-bedroom, two-and-a-half bath home for six yours when you come to Key West, and revel in amenities like a private pool and an ideal location. Located in downtown Key West, this home is a mere one block from Duval Street. Southernmost Point and Beach and the Hemingway...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cozy, dog-friendly condo with views - walk to beach, dining, & attractions1 / 32
    (6)Average
    0.2 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.2 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for a budget-friendly home base and plan to spend most of your time enjoying the waves and exploring, this efficient studio is just the ticket. You and one other traveling companion will be in a prime location, within walking distance to the beach and Key West major attractions....
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!1 / 27
    (12)Very good
    0.1 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 4, 2016
    The location is awesome. The kitchen lay out is a train wreck! It was clean and daily towel and linen and linen service was good. Parking ....good luck. Overall it was a fair...
    Reviewed June 5, 2014
    Superb location, ideal for a few days in Key West. Only small but great outside space. Loads of character, only slight negative is the bathroom could do with a little tlc. But...
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    About this property
    Experience Key West in style with this dog-friendly vacation rental in the heart of Old Town! Up to six guests will enjoy a private hot tub and typical home comforts including a private washer/dryer, street parking, and free WiFi. Situated just one block from Duval Street, this cottage has no...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.0 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two-bedroom, one-bathroom house is the perfect place for your next family vacation to the palm-tree paradise of Key West! With a great location downtown, a private parking space, and easy access to a sandy beach nearby, you'll be all set for fun in the sun. Located a half block from...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Renovated home w/ shared pool & furnished patio - near Duval Street, dogs ok1 / 27
    (11)Very good
    0.1 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 2016
    Close to where we want to be. Have booked this place twice in two years. And plan to rent again for our annual trip.
    Reviewed May 15, 2015
    I stayed here with four of my friends and the location was wonderful close to restaurants close to clubs and only a half a block off of Duval. this is a wonderful place and I...
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    About this property
    This cozy Key West rental comes with a shared pool (complete with a cascading waterfall), a furnished patio area, and space for up to six guests. It's perfect for that next family vacation or tropical getaway with a few friends. Please note that this home also comes with one private, off-street...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Tropical Key West studio w/ shared pool - near beaches & Duval St.1 / 24
    (8)Very good
    0.3 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 25, 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 July 30, 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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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Two rustic cottages w/ private hot tubs & private parking - dogs OK1 / 44
    (3)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Hot Tub
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 2014
    Tradewinds was the perfect place for 6 cousins to stay as we gathered in KW to send my sister's ashes off into her beloved warm ocean. The accommodations were perfect for the 6...
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    About this property
    Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub in the back...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Dog-friendly Key West cottage with a private hot tub & an unbeatable location!1 / 26
    (10)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 13, 2015
    Great location! 1/2 a block off the main street (Duval) and convenient to everything, but in a quiet dead end street. Private parking! (Hard to park anywhere in the Keys...
    Reviewed January 12, 2015
    Its just a few steps away from where all the actions is. Considering the location, it is actually quiet at night. We got ourselves lock out while drinking and partying at the...
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    About this property
    Spend your vacation days snorkeling in the clear coastal waters and strolling the streets of downtown Key West when you stay at this three-bedroom, two-bathroom cottage, which also features a private hot tub and one reserved off-street parking space. The family dog is also welcome to join you for...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Charming studio w/ shared pool, covered patio - a block from shopping and dining1 / 26
    (8)Very good
    0.3 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
    • Washer
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • 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
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Historic, dog-friendly home w/ pool & three hot tubs in an unbeatable location!1 / 50
    (1)Very good
    0.1 kilometres from The Ernest Hemingway Home and Museum
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • Hot Tub
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 11, 2015
    We took over the whole compound with three generations of our family - my family and 4 month old twins in the attic suite, my sister's family and the grandparents on the first...
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    About this property
    Privacy, luxury, and convenience combine in this charming Key West vacation rental. Your large group will enjoy top-shelf amenities including a private, seasonally heated pool and three hot tubs, in addition to home comforts such as a private washer/dryer, cable, and free WiFi. This historic...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    0.3 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dive into the thick of it with this dog-friendly home in downtown Key West. One of Florida's most amazing island towns awaits, right outside your door. Your home is set right on Duval Street. You're never more than a few minutes from any shopping or dining you might need. Higgs Beach is less...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.2 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    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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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Cozy cottage w/ private hot tub, tranquil garden & parking - dogs OK!1 / 32
    (37)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 15, 2015
    We stayed in this property for two days. We had a good time. Staff is friendly. They have everything what we need there. I read reviews about this property and some one...
    Reviewed December 11, 2015
    Nice location. Hot tub, patio nice, porch fun to watch traffic a passerbys with morning coffee. Houe is cute but needs a little TLC. Fingerprints on walls and doors, missing...
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    About this property
    Bask in the peaceful sunshine of Key West and feel all your stress melt away when you stay at this cozy dog-friendly cottage right in town. With a private hot tub in the garden area out back plus all the conveniences of home, what's not to love? Sitting only half a block from all the fun and...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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