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Vacation Rentals nearby Old Town Trolley Tours Key West

Mallory Square, Key West, Florida 33040
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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
    Dog-friendly, tropical escape with central location, hot tub, and shared pool1 / 25
    (3)Very good
    0.2 kilometres from Old Town Trolley Tours Key West
    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
    1.0 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Studio Blu1 / 15
    (1)Excellent
    0.5 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    0.5 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this classic Key West cottage featuring a shared pool and a furnished patio, located within blocks of beaches, shops, restaurants, and museums! You can even bring the family dog for a small nightly fee. If you're here for the sand and sun, several local beaches are located less than a mile...
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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.2 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Washer
    • Balcony
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the ideal spot for your next large group getaway, then look no further than this grouping of three separate Key West condos. Boasting a shared heated pool and hot tub, and space for up to 12 guests, this home makes it easy for everyone to enjoy all of the local attractions....
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    0.8 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this cozy and chic Key West luxury house your home away from home for your next Florida vacation, and revel in a private pool, deck, and covered back porch, as well as close proximity to the beach. You'll be situated only six blocks from the beach for fun in the sun anytime you want it,...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Historic home in Old Town w/ private pool & detached cottage - dogs OK1 / 50
    (2)Very good
    0.5 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 3, 2011
    We spent the month of March at Villa azul in 2008. It was amazing. We discovered Key West in a way I never thought possible...some of our best moments were spent in the oasis...
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    About this property
    Come experience Key West in all its glory when you stay in this dog-friendly historic home featuring a private pool and lush tropical gardens. Your group of up to six will be set for a comfortable and convenient stay, and the detached cottage is the perfect spot for the teenager or grandparent who...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Contemporary seaside cottage w/ private hot tub, shared pool - dogs welcome!1 / 24
    (29)Very good
    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 17, 2015
    My wife and I recently rented this unit for the first week of February. Overall, I’d call it a solid good! We liked the location, with a grocery store and an excellent...
    Reviewed September 2, 2014
    I stayed here this past Labor Day weekend for a friend's bachelorette party. There were 10 of us, and the Heron Hideaway as well as the three other one-bedroom condos in the...
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    About this property
    Surrounded by possibilities for fun and relaxation, this Key West cottage offers up to four guests the chance to bask in the warm Florida sun. Featuring a private hot tub, pristine seasonally heated shared pool, and easy access to a wide range of local attractions, this home puts you right in the...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lovely, dog-friendly townhouse w/ private pool, full kitchen & beach access1 / 25
    (21)Very good
    1.0 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 11, 2014
    It was our first time in Key West and, well, you just never know. I got this one spot on though. The decor is fun. the kitchen is very functional. The two master suites were...
    Reviewed October 25, 2014
    The townhouse is excellent. Location is also a huge positive. Clean and updated. Wifi was easy to access.
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    About this property
    You'll settle into island life instantly at this two-bedroom, two-and-a-half-bathroom townhouse in Key West. With a private pool and lush garden in the backyard, a full kitchen, and a great location near the beach, comfort is never far away from your explorations. Located on the south end of the...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Dog-friendly home w/ detached cottage, private pool, & walk to beach!1 / 24
    (1)Excellent
    0.8 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 10, 2014
    The place was really nice and the staff was very easy to work with. It was a very good vacation and would definitely like to stay there again.
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    About this property
    Come to Key West and stay in this dog-friendly accommodation with two separate living quarters, a private pool, walking distance to the beach, and close proximity to all the major attractions. This home is within walking distance to famous Duval Street and its shops, restaurants, and bars. Higgs...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Family-friendly home w/ private pool, furnished patio, and parking - Dogs OK!1 / 28
    (14)Very good
    0.7 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 9, 2014
    We were very happy with this house rental. The pictures only hold a small window into this gem. Walking distance to Duval (although a cab was only $6 if needed). Great living...
    Reviewed August 12, 2014
    Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking.Cons - across...
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    About this property
    Located right in the heart of Key West, this tastefully-appointed, tropical sanctuary comes with a private swimming pool, enclosed yard, and room for up to six guests. The family dog is also welcome to join you for an additional nightly fee. Take a stroll down to Duval Street and enjoy the many...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.8 kilometres from Old Town Trolley Tours Key West
    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for the perfect Key West vacation rental to host your family reunion or corporate retreat? Your search stops with Curry House Bed & Breakfast, a nine-bedroom, nine-bathroom getaway with historic charm, modern comforts, a private swimming pool, and room for up to 18 guests. Curry House is...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    0.9 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Key West for a fun, action-packed getaway when you stay in this two-bedroom, one-and-a-half bath cabana-style cottage for six and enjoy a private pool and easy access to all the action. Bring along the family dog, too, for a small nightly fee! This home is located right on a bike path,...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Centrally located home w/ private pool 3 blocks to Duval St - dogs OK!1 / 25
    (9)Very good
    0.9 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 28, 2016
    We spent January and February at Casa 625 and loved it. There were definitely some issues with the house when we arrived, but once Rick, the rental property manager, got...
    Reviewed December 23, 2013
    The house is my perfect idea of what a Key West Conce Cottage should be. With Dade County pine walls, heated pool, all modern conveniences and perfect location for quite and...
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    About this property
    Swim in the private pool, head to downtown Key West to soak up the sights, or relax in a breezy dog-friendly home - with this amazing cottage, everything is possible! Your new home away from home sits on a hill only a few blocks from the beating heart of Key West. Shopping, dining, and more can...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 kilometres from Old Town Trolley Tours Key West
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Florida and stay in this private dog-friendly home for six for your Key West retreat and enjoy a private pool, wraparound deck, and patio. You'll be tucked away in a quiet Key West neighborhood, surrounded by lush foliage, and you'll be within walking distance of eateries, a market,...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Cute, dog-friendly cottage w/ patio - walk to shops, restaurants & nightlife!1 / 30
    (31)Very good
    1.0 kilometres from Old Town Trolley Tours Key West
    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 January 16, 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 November 17, 2014
    We had a great stay and will for sure be staying in one of these cottages again. Great location close to nice restaurants approx midway Duval and North 2 blocks. Stayed for a...
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    About this property
    Enjoy one of the most desirable locations in Key West at this studio-style cottage, where you'll have an outdoor patio, dog-friendly accommodations, and wonderful access to beaches, restaurants, and shops! This cottage which is within walking distance of the vibrant nightlife on Lower Duval...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Cozy, dog-friendly cottage w/ patio - walk to shops, restaurants, and more!1 / 25
    (29)Very good
    1.0 kilometres from Old Town Trolley Tours Key West
    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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    1.0 kilometres from Old Town Trolley Tours Key West
    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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    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    • DVD Player
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal for families, this dog-friendly home is perfectly placed for fun in the Florida Keys. Perks like a private pool will keep you comfy between enjoying the sand, sun, and surf of the tropics! While the immediate neighborhood is low-key, this home is still close enough to Truman Avenue to...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.8 kilometres from Old Town Trolley Tours Key West
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Searching for an affordable long-term vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Tune into the Windchime! This lovely studio for two comes with all the comforts you need for an extended stay away from home, along with a...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.7 kilometres from Old Town Trolley Tours Key West
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sink into the comfort of this lovely Key West home for 10, and enjoy a luxurious Florida getaway, complete with private pool and hot tub and excellent location, allowing you to walk to dining and all the sights. This home is located on a quiet street in Old Town Key West, a couple of blocks...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Small families and close groups of friends will love this dog-friendly home for four in Key West! A shared swimming pool and nearby beach access provide everything you need for a great vacation. Your new home away from home rests comfortably by the city's Old Town, where lots of shops and...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1.0 kilometres from Old Town Trolley Tours Key West
    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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    0.4 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Leave your worries behind with a relaxing trip to the Florida Keys courtesy of this lovely vacation home! This traditional home in Key West features modern amenities and a location perfect for sightseeing. Nestled in Key West's old town, this home for four puts you only a few blocks from both...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to Key West for a rejuvenating reprieve and enjoy the patio and private pool at this cozy, two-bedroom home conveniently situated near dining, shopping, and all the must-see sights. Your beloved family dog is also welcome for a small nightly fee. You'll be about two miles from prime Key...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    0.7 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This colorful dog-friendly Florida home has everything you need for an unforgettable vacation, with a private swimming pool and hot tub and walking distance from the beach. Your home sits only a few blocks away from the soft sands and warm waters of Higgs Beach. If you'd prefer some shopping and...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    0.7 kilometres from Old Town Trolley Tours Key West
    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
    Amenities like a shared pool, dog-friendly accommodations, and a fantastic location all make this home perfect for your next trip to the Florida Keys! Your new getaway of choice is only a block away from Duval Street, right near Key West's Old Town. Shops and restaurants are easily accessible -...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Cottage w/ shared pool, private hot tub, & street parking - Dogs OK!1 / 26
    (14)Very good
    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Air Conditioning
    • Terrace
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 4, 2016
    This quaint villa was perfect for our party of 2 (might be a bit crowded for 4 adults, but for 2 kids it should be just fine!) The 1/1 was well appointed with everything we...
    Reviewed September 21, 2015
    We loved our stay here. It was decorated nicely, clean, and quiet. Housekeeping came in daily and did a good job. I liked the setup of the condo a lot; a nice, spacious...
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    About this property
    Treat yourself to a much-needed getaway filled with stress-free days and sun-soaked afternoons when you book your escape to this Key West retreat. Offering the chance to enjoy a private hot tub, street parking, a shared pool, and easy beach access, this home will make sure your stay is one to...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make your next Florida vacation something special with this charming home in Key West. A great location in Old Town provides all six guests of this cigar-style 'shotgun' cottage with something they're sure to love. Surrounded by the historic sights of Old Town, your new home away from home is...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    • Balcony
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Key West and ensure your Floridian getaway is the best it can be when you make this desirable rental your home away from home. Your group of up to eight will experience tranquil comfort and tasteful style in this dog-friendly home with a private heatedpool, luxurious patio area, covered...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    1.0 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated, one bedroom, one bathroom unit comfortably sleeps four guests. From the moment you walk in, you will be amazed by the detail, decor and furnishings. The perfect rental home for those who wish to be just above all the action! You and your guests will enjoy the spacious kitchen;...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.5 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Wi-Fi
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    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to the Keys for your next Florida getaway and set yourself up for comfort and convenience when you stay at this welcoming, well-equipped home with a private pool and charming covered porch. You'll be situated only a mile from South Beach, so the sand and water are always within easy...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.9 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the benefit of being right in the heart of the island. You'll be in the center of Key West within walking distance to restaurants, bars, and shops, as well as all the...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    'Little Paradise' Historic Seaport Old Town Key West1 / 16
    (1)Very good
    0.4 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Garden
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    The house is well equipped and very comfortable. My husband is disabled and the shower was perfect for him but not for someone in a wheelchair. The front steps were very hard...
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    About this property
    Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.6 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Parking
    • Washer
    • Wi-Fi
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking. Here is your dream come true. Centrally located on one of Old Town's most popular streets, nestled in a tranquil corner of a sought-after gated compound with lushly landscaped walkways leading to the...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families1 / 23
    (9)Excellent
    0.5 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Key West Oasis is a perfect warm weather get-a-way with a very private (no view of neighbors) backyard and an enclosed outdoor shower as a plus! The house was recently renovated...
    Reviewed February 27, 2018
    The Oasis is truly a bit of heaven on earth! We have been visiting Key West for a number of years and could not imagine staying anywhere else.This rental is fully equipped, in a...
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.5 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a classic Key West vacation at this charming 1BR apartment in a restored 1920's conch house. This prime Old Town location is just a short walk from Duval Street, the historic seaport, beaches, dining, and one-of-a-kind shops. Guests enjoy use of the heated pool. ABOUT THE APARTMENT This...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Sunny View1 / 24
    (2)Excellent
    0.6 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 5, 2014
    The property was exactly as described and in tiptop shape. Everything was ready for our stay, the house was comfortable and a fair value.Also, the folks from at Home in Key...
    Reviewed February 9, 2011
    We had a wonderful time. The weather was great. The cottage was in the perfect location, very clean and filled with everything we needed. It was better than the condo we had...
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    About this property
    Lovely 1 bed/2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street. Adorable, affordable, and a great location! You bet! Sunny View is the monthly rental Key West perfect escape for a couple or singles looking to get away from it all in...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    0.7 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
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    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    YOUR PRIVATE GETAWAY IN KEY WEST, FLORIDA.  This beautifully historic 2 bedroom 2 bath home is conveniently located in Old Town Key West, FL. Just a short walk from everything you could dream of, for your island vacation. Just 5 blocks from the famous Duval Street. Two blocks from the seaport,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private outdoor kitchen to able to enjoy cooking your favorite dish while enjoying the large outdoor space. You could easily pass by this jewel of a home without ever knowing it was there. Located down Wong Song Alley behind a private fence, just a few steps from the pool and you've reached your...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.7 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private outdoor space to enjoy this unique cottage within walking distance of great restaurants and shops. Located in Old Town in a small, quiet compound of cottages sits William's Loft in one of Key West's most desirable neighborhoods. A secluded compound surrounded by lush tropical foliage make...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    0.3 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully restored private cottage located in Old Town Key West. Have you been dreaming of living like a local in Key West? Your dream can come true. Green Orchid offers a true Conch Cottage experience on a narrow lane in one of the last historic Old Town neighborhoods. Situated on a lane that...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Luxury Rental Old Town Key West Close to Beach. Private Heated Pool1 / 21
    (11)Very good
    0.8 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 27, 2018
    This home was spectacular. It was everything that was advertised and much much more. The out door pool was refreshing each morning for a swim before starting our day and the...
    Reviewed July 29, 2018
    This home is beautifully decorated and modern. It has everything you need to make your stay comfortable. Very modern. Nice pool right out back. Close to downtown. Tucked...
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    About this property
    Beautiful Keywest home blocks from Higgs Beach, playgrounds, restaurants, and famous Duval street. This rental includes use of 2 beach cruisers. Private Pool and front yard. Tropical Oasis. Includes washer and dryer. This is a beautiful Key West home in old town. All amenities included. Dogs are...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Quilted Giraffe1 / 25
    (3)Excellent
    0.9 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 29, 2017
    Charming historic home, comfy beach cottage feel. GREAT LOCATION, beautiful pool area great for dining under the stars or a relaxing day in the sun. If your lucky you might get...
    Reviewed June 7, 2011
    This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is...
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    About this property
    Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes you from its quiet neighborly front porch facing tree-lined Elizabeth street to its private deck and heated pool in the rear. The location called Solares Hill is a part of Old Town...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEWTON'S NEST (Monthly Rental) Newtons Nest (Monthly Rental) A quiet little refuge tucked away in Old Town where you can set up roost, stay for a month or more and enjoy a leisurely existence. A 1 bedroom condo that has been lovingly restored to showcase beautiful Dade County Pine walls,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.6 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by. You know the feeling. Rushing to go on vacation, to the airport, driving in traffic, so many people around you doing the same thing, finally in Key West at your home...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private fenced outdoor space to enjoy your private plunge pool and the large outdoor space for lounging and dining. Adorable, affordable, and near all the action.... You bet! Coconut Cottage is the perfect escape for a couple or singles looking to get away from it all in paradise… Located in a...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Island Wind1 / 23
    (11)Excellent
    0.9 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 17, 2018
    We stayed a week and thoroughly enjoyed the rental property. Great pool, private location with good security behind gated entry. The unit was super clean, well stocked with...
    Reviewed May 26, 2016
    Spent a a week here. We loved everything about it. Great neighbors and relaxed atmosphere. House was absolutely perfect. Everything you need is there, just bring a bathing suit...
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    About this property
    Located in a quiet community of Windward Park, only a short walk to Duval Street, with a large shared pool, Island Wind is a true gem in between our rentals Welcome to a tropical sun drenched oasis in the heart of Old Town Key West. This charming 2 bedroom 2 bath Bahamian style townhome,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.8 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique 1 bedroom, 2 bath cottage is about to become your home away from home! Step in to a tranquil community on a quiet lane, only blocks to Duval Street and discover BOAT HOUSE! This spacious cottage with a large private covered deck, just perfect for enjoying an afternoon cocktail or a...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Verandah1 / 24
    (11)Very good
    0.3 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 13, 2012
    We enjoyed everything about our wonderful home in Key West. We felt right at home, great location, we could walk everywhere, short drive to the beach, harbor, and restaurants...
    Reviewed September 2, 2011
    Everything was great about my stay. At Home Key West is great to work with and very easy to get in touch with should an issue arise. The location of this house is great, and...
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    About this property
    Beautifully designed yet comfortable private home that you may never leave, only to go outside to your private pool and secluded space to hang out. Tucked away on historic Frances Street lies your island escape… Verandah is a stunning monthly vacation rental -- two bedroom two bath home with a...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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