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Holiday Rentals near The Ernest Hemingway Home and Museum

907 Whitehead Street, Key West, Florida 33040-7473
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    Travellers to Key West are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!1 / 25
    (18)Very good
    0.1 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH1 / 61
    (9)Excellent
    0.3 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 1 Bathroom, Sleeps 4 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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    Dog-friendly home w/ private pool - walk to the beach and restaurants!1 / 26
    (2)Excellent
    0.3 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Terrace
    • DVD Player
    • Washer
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2018
    Had a great surprise birthday weekend in Key West. The house was fantastic! Very clean and bigger than the pictures make it seem. Loved the heated pool, and close walk to Duval...
    Reviewed 23 January 2017
    3 levels of beautifully decorated accommodations! Walking distance to famous Duval St, bars, restaurants and shopping. Loved it!
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    About this property
    A Key Escape Escape to the Florida Keys for a relaxing vacation in this three-bedroom, two-and-a-half bath home for eight (six comfortably) with a private pool and walking distance to the beach and Duval Street. And your favorite canine friend is also welcome for a small nightly fee. This rental...
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    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool1 / 42
    (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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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Private Garden
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 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 13 October 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
    Bahama House 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...
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    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    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
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Galleria - Andy's Attic 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...
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    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Contemporary dog-friendly cottage with easy beach access and shared pool1 / 31
    (33)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2017
    We LOVED our stay at the Andros Suite! The condo itself was clean and comfortable. The courtyard was breathtaking! The couple that are the property managers are PHENOMENAL...
    Reviewed 20 May 2016
    We loved our stay at the Andros Suite. The unit was very comfortable. They even had daily service who came in and cleaned and provided fresh towels (which was unexpected...
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    About this property
    Old Town Garden Villas - Andros Suite Book your well-deserved getaway to this dog-friendly Key West home. With a prime central location near Duval Street and access to a shared pool, this home will let up to four guests and your happy puppy (for a small nightly fee) unwind in style. Notice:...
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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    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 4 March 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 1 March 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
    Old Town Garden Villas - Bermuda Suite 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...
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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    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 30 October 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 27 April 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
    Old Town Garden Villas - Little Havana Suite 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!...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    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
    Carriage Courtyard *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* If Key West is on your travel itinerary, make this lovely rental for six your home away from home and spend your time lounging...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Heart of Old Town getaway, perfect romantic retreat -near the action1 / 26
    (1)Excellent
    0.1 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2019
    It's not big, but it's plenty for two people. The a/c unit was sufficient, the bed a little squeaky but comfortable, bathroom small but sufficient. Everything was clean and...
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    About this property
    Truman * Duval - Studio A 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...
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    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Deluxe, ground-floor studio w/ view of the courtyard and pool - close to shops1 / 26
    (14)Very good
    0.3 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 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
    Papa's Hideaway #3 - For Whom the Bell Tolls 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...
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    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Romantic & elegant studio-style cottage w/ private hot tub - dog-friendly!1 / 45
    (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 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
    Royal Palm 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
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Colorful condo w/ deck, balcony & shared pool - near downtown & beaches1 / 39
    (23)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 April 2015
    Very well decorated an equipped with everything needed. Nice open area, the pictures do not do it justice. Larger living area and dining than the photos show. Two nice balconies...
    Reviewed 6 August 2014
    Excellently furnished, Immaculately clean. Completely up to date appliances and amenities. (Washer & dryer just off the kitchen!) Tip-Bring your own laundry...
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    About this property
    Casa Cubana * Duval Square R14 Find a colorful, comfortable escape in the heart of Key West at this two-bedroom condo, where you'll enjoy a private deck and balcony, a community swimming pool, and easy access to beaches and downtown. This well-appointed condo sits in the heart of historic Key...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    0.1 kilometres from The Ernest Hemingway Home and Museum
    Studio, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Truman * Duval - Unit B Enjoy this one bedroom apartment for your next getaway to Key West! Perfect for couples, this romantic spot is newly remodeled and will provide everything you need for a quick weekend escape! Beach towels are provided for your use. What's nearby: Located in the heart of...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bathrooms, Sleeps 4
    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
    Yellowfin Ledge On Duval 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...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Romantic dog-friendly cottage w/shared pool, tropical decor, & easy beach access1 / 19
    (25)Excellent
    0.2 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2014
    Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
    Reviewed 19 August 2014
    My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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    About this property
    Old Town Garden Villas - Caribbean Suite Book your romantic retreat to this dog-friendly Key West cottage. Enjoy the shared pool and a great location off of Duval Street. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am Located a few blocks from the Florida Keys...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    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 14 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 1 January 2015
    Three generations, nine people, stayed here over Christmas. We each had space to be by ourselves, and we all had space to get together. Nine of us sat around the table in the...
    Reviewed 3 September 2014
    I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
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    About this property
    Almost Southernmost Retreat 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...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
    0.1 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Hot Tub
    • Patio
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Colada *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. This charming home features a gorgeous, open floor plan, a heated, outdoor pool, beautiful landscaping, an adorable front porch for...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    0.2 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Cable/satellite TV
    • Private Garden
    • Balcony
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kate's Krawl Off Duval The sunny paradise of Key West beckons, and this dog-friendly home is the perfect place to stay, with a private patio ensuring relaxation is never far away. Located just steps from desirable Duval Street, this home makes it easy to experience all the best attractions in...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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 15 May 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 13 July 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
    Truman Suite 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...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    0.3 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Duval Hideaway Unwind in the heart of Key West's historic district with a dip in condo's hot tub ! The back patio here offers room to grill out and relax with your group after a long day enjoying all the island has to offer. This suite is located on historic Duval Street, where you'll find some...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Dog-friendly condo w/ balcony, shared pool - near shops & restaurants1 / 38
    (11)Very good
    0.1 kilometres from The Ernest Hemingway Home and Museum
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Balcony
    • Terrace
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 2016
    This was at the southern end of Duval so not quite as noisy, which was nice. The restaurant below did play music in the morning which was annoying at times and the rooster would...
    Reviewed 14 March 2015
    The apartment was very comfortable and spacious. It is centrally located and although it's a little noisy at meal times, it is not a problem at night. It does need some minor...
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    About this property
    Casa Key West * Duval Square R32 Experience the beachy retreat you've been searching for at this dog-friendly Key West condo, where you'll enjoy a private balcony, a shared swimming pool, and a wonderful location for exploring. Beautifully positioned to overlook the gardens of Duval Square, this...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Cute, dog-friendly cottage w/ patio - walk to shops, restaurants & nightlife!1 / 30
    (31)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    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
    Monroe Suite 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 which is within walking distance of the vibrant nightlife on...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    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
    Meaning of Paradise *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Escape to paradise at this family-friendly, three-bedroom Key West townhouse with a full, modern kitchen, furnished deck, and a...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Quaint romantic cottage with street parking, close to the beach & adventure!1 / 24
    (49)Very good
    0.1 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 2016
    My 8 friends and I stayed here this last week and had a great time. It's directly off duval and has three king beds with a pullout couch. The beds were very comfortable while...
    Reviewed 2 December 2015
    Right in the heart of Duval and nicely tucked away from the street. Rental was very clean and orderly however it did have a strong musty smell so we purchased multiple air...
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    About this property
    Hemingway's Shadow *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* Whisk your special someone away for a tranquil retreat when you book your next vacation at this Key West cottage. Putting you...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.2 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Duval Delight 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...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    0.2 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Galleria - Carey's Corner 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...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Historic, dog-friendly cottage in the heart of Key West w/ private hot tub1 / 45
    (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 28 June 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 1 July 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
    Almost Southernmost 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...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Dog-friendly studio w/ private deck & hot tub - 1 block to Duval St!1 / 29
    (4)Very good
    0.1 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
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    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 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
    Traveler's Palm 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...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    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 17 November 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 11 November 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
    Duval Corner 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...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Tropical Key West studio w/ shared pool - near beaches & Duval St.1 / 25
    (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
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    • Washer
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    Suitability
    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 31 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
    Papa's Hideaway #4 - Islands in the Stream 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,...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    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
    The Galleria - Coral Cove 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...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Historic vacation rental with a private pool - dog-friendly!1 / 39
    (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 16 June 2015
    My husband and I stayed here with 2 other couples. The location was absolutely perfect for walking or biking to anywhere on the island. The pool and outdoor area were also...
    Reviewed 30 July 2014
    This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management...
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    About this property
    Coconut Palm 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...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.3 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Pelican *Please note that this home requires minimum stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. You'll be mere steps from dining, shopping, nightlife, and a wide variety of attractions at this darling Key West home, perfectly situated on...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Colorful, dog-friendly cottage w/ private pool & all the comforts of home1 / 50
    (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 30 October 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 25 July 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
    Almost Southernmost Too 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...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok1 / 49
    (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 (Heated)
    • Patio
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 December 2014
    The rental is great and in an excellent location. We had a group of 6 and had no issues. Note: unlike some rentals there is nothing in the house if you plan to cook. You...
    Reviewed 25 July 2014
    Everything was easy and perfect check in wise. Rooms were clean. Will stay here again. Walked to all bars and loved the tall ceilings.
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    About this property
    Tropical Retreat 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....
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Cozy tropical suite half a mile from the beach - dog OK1 / 22
    (8)Average
    0.2 kilometres from The Ernest Hemingway Home and Museum
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    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 8 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
    The Galleria - Claude Monet Suite 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...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    0.4 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sweet Serenity *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* Amenities like a shared pool, dog-friendly accommodations, and a fantastic location all make this home perfect for your next trip to...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    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
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Galleria - Matisse Manor 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 covered porches are a great place to enjoy the evenings. What's nearby: This cozy studio apartment is located in a quiet...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    A Key West gem w/ a private pool - close to shops & restaurants, dog-friendly1 / 25
    (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 11 July 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 7 June 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
    Helen's Hideaway 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. Two dogs...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.1 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
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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
    Key Lime Calypso 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...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Classic Key West cottage featuring shared pool, courtyard, covered front porch1 / 57
    (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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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2017
    We stayed here after having a rough go of it in Miami and we fell in love. My kids said "Mom we should have stayed here the whole time, this place is awesome." The pool...
    Reviewed 10 September 2015
    Beautifully decorated Old Key West home. Our kids (12, 5) loved seeing the Iguana in the courtyard. The pool was nice to relax in after a day of sightseeing. Beds were...
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    About this property
    Papa's Hideaway - Garden of Eden 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...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Galleria - Salvador's Suite 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...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Cheery beach getaway near local attractions, w/shared pool & easy beach access1 / 56
    (8)Very good
    0.3 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Terrace
    • Balcony
    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2014
    Highly recommend this facility to anyone who is looking for a conveniently located, quiet, easily acessable 2 bedroom / 2 bath condo. Our week stay was everything we could...
    Reviewed 12 May 2014
    Three friends that I have known since first grade and I traveled to Key West for a week to celebrate the year we all turn 60. Stayed at Shipyard Perch. it was perfect. The 2...
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    About this property
    Shipyard Perch Treat yourself to a stress-free vacation filled with sun-soaked days when you book your trip to this Key West condo. With room for up to four guests to a shared pool and beach lifestyle, this home will make it easy to slip into vacation mode! Located in the Truman Annex, a quick...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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 14 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
    Papa's Hideaway #1 - Torrents of Spring 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...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Cozy, dog-friendly townhouse w/ shared pool & courtyard - walk to Duval & more!1 / 26
    (24)Very good
    0.2 kilometres from The Ernest Hemingway Home and Museum
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2017
    What a beautiful place, the court yard was unbelievable all the love and care that has gone into all the plants, so peaceful to sit and relax and regroup from the Key West...
    Reviewed 1 June 2016
    Secure, gated community. Each unit was part of a duplex/townhouse. Close to Duval Street without all the noise. Home was clean and very spacious. Tons of drawer space...
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    About this property
    Old Town Garden Villas - Abaco Suite Whisk your special someone off to this enchanting Key West townhouse. Enjoy the shared pool and courtyard. The family dog is also welcome to join you for an additional nightly fee. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.0 kilometres from The Ernest Hemingway Home and Museum
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Truman * Duval - Two Bedroom 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....
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Bright, clean home w/private hot tub & shared pool, close to everything, dogs ok1 / 33
    (13)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
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2016
    The condo was beautifully clean, very spacious and well equipped. The beds and pillows were amazingly comfortable and the maid service was very efficient. The condo's location...
    Reviewed 10 July 2016
    Stayed here in June as a family of 4. We were expecting a double and 2 twins but when we arrived the twin room was set up as a double. However, we discovered there was a sofa...
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    About this property
    Spa On Duval * Duval Square R11 This cozy, well-appointed condo offers easy access to Duval Street and all of Old Town Key West. Featuring private, furnished patios, an outdoor hot tub, a gorgeous shared pool, covered private parking, and room for up to six guests (four adults, comfortably), this...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Cute 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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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 May 2017
    Great adult week 1 block away from Duval street. the house was very clean! we had the best time ever!!!
    Reviewed 7 February 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
    Sea Breeze Enjoy one of the most enviable locations in Key West when you escape to this two-bedroom condo with a private covered porch, wonderful access to beaches, restaurants, and the Old Town area. This gated property sits in the heart of Old Town Key West, just one block from the legendary...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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