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Holiday Homes near Southernmost Point

Whitehead Street, Key West, Florida 33040
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Shelleys Rooftop Hideaway1 / 15
    (7)Excellent
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    BEST LOCATION & PRICE! King Suite w/ Jacuzzi steps off Duval St.-Mango Hideaway1 / 18
    (7)Very good
    0.6 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Duval Balcony - Street Suite1 / 15
    (3)Very good
    0.6 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    PARKING,2bd/2bth,20yrd TO DUVAL,FREE OLD TOWN SHUTTLE,MAJOR ATTRACTIONS NEARBY1 / 41
    (1)Excellent
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Patio
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2018
    Best part, it is right off of Duval and close to so many things to do. The beach is 5 minute walk and the community pool is an amazing unused gem. Free bus to lower Duval is...
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    About this property
    Check out the new 'Duval Loop' that ferries you around Old Town for free and is located at the corner of this homes block!!!!Map is included in pictures. Hemmingway House, Lighthouse, Butterfly World, Southern Most Point, Conch Tour Train, Beach, Galleries & Restaurants are all located within a 5...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Manana Conch Cottage1 / 41
    (8)Excellent
    0.6 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2012
    We've stayed in 4 different vacation rentals for a month or more at a time, and I think we enjoyed Casa Manana the best. Lots of character, great location, friendly cats and...
    Reviewed 2 July 2011
    The home was wonderful & the perfect size for our family. It was close to everything & we enjoyed the nearby church bells while sitting by the pool. We were surprised...
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    About this property
    Casa Mañana at 800 Virginia Street is perfectly situated for the guest who wants to enjoy Key West at its finest. Located just three blocks from Duval Street, home of world famous watering holes, shopping, and dining, this Old Town jewel is just steps away from Fausto’s Food Palace, Sandy’s Café,...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    LOCATION! Feel like a Local! Spacious Suite steps off Duval St.-Eyebrow Suite1 / 24
    (4)Excellent
    0.5 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    This was our 2nd time staying with Andrews Inn and Cottages. They are amazing!! The staff is very accommodating, the suites are wonderful, and we can't wait to go back. I highly...
    Reviewed 23 March 2017
    Eyebrow House has a ton of room, lovely front porch and rear patio. The negative for senior citizens is that it has only a queen bed and hideabed which works for kids, not...
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    About this property
    The Eyebrow House is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local...
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ibis1 / 24
    (2)Very good
    0.7 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 2011
    My location was so convenient that I could walk everywhere and I did. I loved the fact that it was so quiet at night. When I needed service on the microwave, it was provided...
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    About this property
    IBIS - Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home. Just a couple of blocks to Duval Street, walking distance to restaurants, shopping and attractions of Old Town Key West. What a great location; park your car and jump on your bike for a relaxing...
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH1 / 61
    (7)Excellent
    0.2 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Porch
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 February 2018
    Just how close do you need to be to Duval not be hinder by the noise other places have mentioned - this is the place. It is beautiful, colorful, and comfortable place to wake...
    Reviewed 1 September 2017
    Awesome setup. Beautifully decorated, fully equipped, close enough to walk to just about everywhere you want to be Although I would recommend a bike, cart , or moped.
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    About this property
    La Dolce Vita is just steps to Duval Street! 'La Dolce Vita' and is a totally renovated condo. Please check out our calendars for availability, photos and video. Everything is brand new from floor to ceilings! 14 foot high ceilings with back lit crown molding in every room for a cozy,...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.4 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Ocean Views
    • Parking
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Cockadoodle Cottage ~ Weekly Rental1 / 10
    (4)Very good
    0.1 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Talk about nice. Really great to have place to cook, wash clothes, close to everything, great!! Will go again for sure
    Reviewed 19 March 2017
    Walking distance to everything was a big plus. Never had to get in our car. Off street parking was nice to have. House was comfortable and had two outdoor spaces. Only two...
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    About this property
    Key West cottage architecture has been thoroughly 'time-tested' in 'island life and culture' in this somewhat infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.' Since its original construction in the early 1900's this note-worthy Cockadoodle...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Grande1 / 24
    (4)Excellent
    0.3 kilometres from Southernmost Point
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2015
    This was our second year at Casa Grande and I recommend highly if you're a group of 8-12 people. Beautiful location near 1100 block of Duval. Nice large pool in backyard...
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    About this property
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa Grande...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Tranquility1 / 24
    (29)Very good
    0.7 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Balcony
    • Cable/satellite TV
    • Terrace
    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    Tranquility is a true Key West experience...clean cottage, clean pool, great location! Plan to rent bikes as parking is VERY limited and once you park your car you will not...
    Reviewed 29 June 2015
    The Tranquility Cottage (#5 at The Colony Cottages) is adorable. The cottage is bright, cutely decorated, and the compound is quite inviting. It is conveniently located and an...
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    About this property
    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked for a Key West vacation rental Florida. Fabulous artwork, fun collectibles, beautiful stained glass all give this cottage the unique feel that keeps...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Key West Ginger Whole House1 / 23
    (51)Very good
    0.1 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Hot Tub
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We stayed here for 10 days in April. Very clean and well stocked with everything you needed. Only a 1/2 block off Duval St. but still very quite. Close to restaurants and...
    Reviewed 13 July 2016
    I just stayed at the Key West Ginger House with my husband and family and my big dog and it was great. The location is the best since it is on the Southernmost Point, close to...
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    About this property
    KEY WEST GINGER HOUSE - An absolute jewel of a Key West vacation home a few doors from Duval Street, named for the breathtaking ginger plants blooming in our tropical paradise. Key West Ginger House is a historic home built in 1933, the epitome of what you have in mind when you are thinking...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.4 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will love this quiet tree-top studio in the heart of Old Town Key West. Located just a block away from the Historic Light house and Hemingway house and very close to Duval Street. This is a cosy studio ideal for one person or a couple looking for a reasonable Key West get-away. There is...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Amelia Home1 / 24
    (54)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2015
    What a great place to stay. Location is perfect. Everything you need is supplied. Decor and Landscaping were also wonderful. Already talking about next years stay. Nothing...
    Reviewed 3 April 2014
    Amelia Home was a great place to stay and experience Key West. The house is very clean and in excellent condition. The pool made the stay.The location is great. You can walk to...
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    About this property
    AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Amelia Home. This is the Key West Florida vacation home rental you have been seeking, tucked away in one of the...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Dreaming1 / 24
    (58)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2017
    Nice and quiet with pool. Two bed rooms and two baths. Nice and clean house only draw back, has limited parking since we had 2 cars.
    Reviewed 22 July 2015
    Very Nice! Photos are true to form. Needed a place we could bring our small dog. Perfect distance from Duval. Pool was small but we had only 4-6 max (plus the dog). Grilled a...
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    About this property
    TROPICAL DREAMING -- A distinctive private Key West vacation home with sparkling pool, Tropical Dreaming is the classic example of the best of both worlds while vacationing in Old Town. Only a short stroll over to Duval Street, where entertainment and activity abounds or 4 blocks to the Atlantic...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Valhalla1 / 25
    (53)Excellent
    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Beautiful villa. Peace and tranquility within easy reach of the heart of Key West. The most well-equpped kitchen I have found!
    Reviewed 13 December 2017
    Two blocks from the quiet end of Duval. Three blocks from the Southernmost Point. Ample on street parking and you can walk to Louie’s Backyard. Tim and his team at HH are first...
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    About this property
    This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Caribbean Cottage ~ Duval Street Key West ~ Weekly Rental1 / 14
    (5)Very good
    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    Our group of 4 stayed here the first of August 2017. We thought the location was perfect with Duvall street, convenience stores and multiple bars & restaurants nearby. The...
    Reviewed 26 May 2017
    Best bed ever! Accommodations were everything listed and more. Easy check in and out. Floor plan gave us (2 couples) privacy. Pool was refreshing, even had a visit from a...
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    About this property
    Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Historic Preservation Award Winner! This licensed vacation home was recently featured on Key West's historic home tour and is available to rent monthly. We recently completed a massive 6-month remodel, making this one of the more spectacular vacation homes you'll find for rent in Old Town. In...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Twice as Nice ~ Weekly Rental1 / 17
    (4)Excellent
    0.1 kilometres from Southernmost Point
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2017
    Great houses in a perfect location. Everything was very clean and to the highest standard. Easy to book. Highly recommended.
    Reviewed 28 October 2016
    We rented. Other cottages for a family vacation. Both units were better than expected for all that we wanted to do. The rooms were spacious, the pool area was private and...
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    About this property
    In this case... 'Two is definitely better than One'! A rare set of early 1900's 'twin-cigar maker's cottages' perched on the southern end of famous Duval Street. The Twice As Nice vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Duval On The Square1 / 24
    (4)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2015
    The place was spacious, clean and right on Duval. The only somewhat negative was the noise from the restaurants on the square, but would not stop me from renting this unit again...
    Reviewed 10 April 2015
    The condo is very well maintained. Furniture is clean and appropriate for the location. We found the location to be excellent as it is away from the hustle and bustle of...
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    About this property
    DUVAL ON THE SQUARE - Located at the Duval Square townhomes directly on Duval but above all the hubbub. This Key West house rental near Duval Street is built on the second and third story of the complex with the first floor being a wonderful collection of cafes and bistros. The square itself is...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just as you're inspired by an island oasis, so is this tropical Island Oasis Garden Home vacation rental. Cleverly hidden in the heart of Old Town Key West, this small private gated oasis uses a traditional Key West style architecture of tin roofs, wooden planking, sash windows, and charming front...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Vintage Luxury Cottage ~ Weekly Rental1 / 11
    (6)Very good
    0.3 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Loved the cottage. Loved the location. Very quiet even though it’s steps from Duval. The only reason I don’t give it five stars were little details such as the shower drain was...
    Reviewed 5 January 2018
    Read the comments about shade around pool. True, but we thought it was a wonderful place, When at the beach most of our time is under an umbrella, Immaculate and nicely...
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    About this property
    Without a doubt, one of the rarest private Key West vacation cottages available. Situated in one of the most requested locations in Old Town Key West, this luxury renovated turn-of-the-century Vintage Luxury Cottage vacation rental is hidden just off upper Duval Street in Old Town. Enter the gate...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Two Bedroom Historic Hideaway Olivia Retrea Private Pool  Key West- Monthly1 / 26
    (1)Excellent
    0.6 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2015
    This is a lovely home that is obviously well loved by the owners. Everything is well maintained the pool is sparkling clean. There is beautiful artwork throughout the home. It...
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    About this property
    Look no further you have found a beautiful 2 bedroom 2 bath 'Shot-Gun' house in the heart of Old Town Key West, just 4 blocks from Famous Duval Street. This great property is very spacious and will accommodate up to 6 guests comfortably. There is a Fully equipped kitchen with a full size dining...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Poinciana House1 / 25
    (48)Excellent
    0.6 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    My husband and I took our 13 year old daughter to the Poinciana House. Location is perfect for bikes: It was far enough from all the crazy noise of Duval street, but close...
    Reviewed 14 June 2017
    The house was a 1/2 block off Duvall Street. Was close to all restaurants and attractions. The house was very cute and clean. The pool was fantastic. We would definitely stay...
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    About this property
    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    0.2 kilometres from Southernmost Point
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Parking
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in style in the heart of Key West's historic downtown, where you're steps from the beach and all Duval Street has to offer! Your back patio houses a private hot tub, dog-friendly accommodations, and grill, perfect for lounging with the group after a long day of play. You're located on...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Duval Street Suite1 / 22
    (44)Very good
    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 April 2018
    This townhome-type rental has a queen bed and a bathroom downstairs, and a king (with bathroom) in the loft. The downstairs sofa is a pullout bed, and an additional folding twin...
    Reviewed 18 February 2018
    We stayed in this condo mid January for two weeks. First let me thank Tim who was very helpful. The apartment was very clean, the beds are comfortable. The kitchen is well...
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    About this property
    It's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. From your private and expansive...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Top Of Duval- 6 Bedroom Penthouse1 / 26
    (13)Excellent
    0.6 kilometres from Southernmost Point
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 April 2018
    The location is perfect -- nearly equidistant from the Atlantic and the Gulf and in the midst of Duval Street restaurants, shops and bars. And, the rooms are great -- attractive...
    Reviewed 23 January 2018
    The Top of Duval is amazing....great location, clean, fully stocked! June was excellent to work with
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    About this property
    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    Seaside Place Key West FL 5 Bedroom House 4 Baths1 / 32
    (39)Excellent
    0.1 kilometres from Southernmost Point
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • DVD Player
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 January 2017
    What a great house for our one-week getaway over the New Year holiday! We had a group of 11 people, and we were all comfortably housed inside the well-appointed home. From the...
    Reviewed 30 December 2015
    This is a most beautiful home! Perfect for our 10 family members. The kitchen is fully equipped for all family needs. Each bedroom is beautifully decorated with its own theme...
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    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Key West Spa Villa ~ Weekly Rental1 / 22
    (7)Average
    0.2 kilometres from Southernmost Point
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 April 2014
    The house we rent was absolutely beautiful, the pictures do not do it justice. The house was extremely clean, the pool and hot tub area were wonderful. The little extras such...
    Reviewed 30 April 2014
    If you're looking for an amazing place to stay, this house is for you! In walking distance to everything. The house was clean and comfortable, the pictures don't do it justice...
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    About this property
    This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites. Opposites attract...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    0.6 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, private pool, furnished patio, and off-street parking for two...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Duval Square1 / 22
    (47)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2018
    Super location on Duval Street no far from the Southernmost Point and within walking distance to great restaurants and entertainment. This condo has everything you need for an...
    Reviewed 16 January 2018
    Absolutely beautiful, we so enjoyed this location and the condo itself. Safe, Secure, Parking, Bike racks inside the garage Clean, well stocked, beautifully...
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    About this property
    There's no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens leads to a...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Osprey1 / 48
    (45)Very good
    0.7 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2016
    We stayed at the osprey in bungalow #8. This place was clean with a very comfortable bed, sitting area, kitchenette with a full size refrigerator and a nice deck for morning...
    Reviewed 22 March 2015
    We walked everywhere and, in fact, never moved our vehicle. The cottage is cozy, clean and comfortable and the pool is great. Having a washer and dryer on the property was...
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    About this property
    OSPREY - This bright and colorful studio Key West rental cottage is located in the same small community once known as The Colony Suites, a charming and secluded Key West style compound nestled in the heart of historic Old Town Key West. This is absolutely the ideal location just three blocks from...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Conch Haven Old Town 1/1 MONTHLY Rental1 / 12
    (2)Very good
    0.5 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Patio
    • Washer
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 April 2018
    We stayed in 1st level of 1863 house that has been updated extremely well; state of the art appliances, big & small--has complete sets of Cuisinart pots/pans, Fiesta Ware...
    Reviewed 28 November 2016
    This property is very convenient to everything in Key West. We walk every day--we can go to the beach, the sunset, Duval, and all of the various attractions on foot. The...
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    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Tree House Old Town 2 Bedroom MONTHLY Rental1 / 16
    (5)Very good
    0.5 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Porch
    • Outdoor Dining Area
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 January 2017
    The Tree House is appropriately named, tucked away on quite street a couple blocks off fun and busy Duval, the windows open wide, right into the canopy of mature trees, as does...
    Reviewed 19 October 2016
    I am a 31 yr old entrepreneur that can work from anywhere and was looking to escape from the brutal New Jersey winter we were having. So I booked a the entire month of March in...
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    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    On Hemingway's Rounds ~ Monthly Rental1 / 14
    (1)Excellent
    0.7 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2016
    Very comfortable home, well furnished, very homey. Great location. Management company very responsive to all questions and needs. We loved our stay at On Hemingway's Rounds.
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    About this property
    Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.6 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When I went to preview this townhome called Cabana Boheme, I was intrigued by the name. And so it was fitting to its nom de plume, that I drive the 10 blocks in our hand-painted conch cruiser truck, transformed into rolling art by local mural artist Rick Worth. Key West is like that, as much a...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hemingway's Library – MONTHLY Rental1 / 20
    (3)Very good
    0.7 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2017
    The Hemingway Library is a beautifully appointed house in an ideal location. There was absolutely nothing to fault it on except we wished we could have stayed longer.The house...
    Reviewed 12 July 2017
    The location half a block from the middle of Duval means all is close at hand. So many restaurants to choose from all easy walking distance. Having the parking space was also...
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    About this property
    This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway's Library, the residence maintains the mystique of the island's most famous author by way of books, pictures, and...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.3 kilometres from Southernmost Point
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'In-the-know' travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Key West Dreamin' ~ Weekly Rental1 / 20
    (12)Very good
    0.2 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2016
    Just looking at the pictures of the home as I write the review makes me wish I was still there. Stayed with VHKW for the 2nd time at this property and it was just perfect. The...
    Reviewed 22 June 2016
    Love this place, it has a great outdoor space and relaxing living room. Gas grill for cook-out was great. Great location close to our favorite restaurant El Siboney!
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    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New 1,500 sq. ft. townhouse with 2 large bedrooms with king beds, 3 full bathrooms plus covered deeded parking for your car. Fully equipped kitchen. Sleeps up to 6 comfortably as the downstairs living room has a queen sleeper and full bath. Luxury furnishings and appliances throughout make this...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.5 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whisk your special someone away for a tranquil retreat when you book your next vacation at this Key West cottage. Putting you right in the middle of the action while surrounding you with relaxation, this home offers room for two and street parking for convenience. Located just a block from the...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.3 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Treat your group to a tropical getaway at this dog-friendly Key West retreat. Featuring room for up to six guests and a cute canine companion (for a small nightly fee), street parking, a private hot tub, and a shared pool, your vacation promises to be one to remember. This home is nestled in a...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.5 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Parking
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for a convenient home base for your Key West adventure, consider this two-bedroom, one-bathroom vacation rental. Up to six guests will enjoy the convenient location, a private hot tub, a fully equipped kitchen, and more! The family dog is also welcome to join you for an additional...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.2 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • Terrace
    • Balcony
    • Internet Access
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best of Key West's historic district from the comfort of this condo! An upstairs balcony gives you a bird's eye view of the town, and you'll be steps away from shopping, dining, and the beach. Guests staying at this suite will experience historic Duval Street up close, from fine...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Villa Deja vu Key West ~ Weekly Rental1 / 36
    (8)Very good
    0.3 kilometres from Southernmost Point
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 February 2018
    The home was just as described. The location made for easy walking to any of the local attractions. There are several restaurants and cafes within a few blocks. The french cafe...
    Reviewed 13 May 2016
    This property was truly more than we expected. The home was lovely, but our expectations were exceed by the outside living space. The pool is perfect for 8-12 people. There is...
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    About this property
    You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get that sense that you’ve been there before? When I first visited this vacation rental house, it happened to me. My mind sparked, the place seemed wonderfully familiar, and I felt an...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    0.3 kilometres from Southernmost Point
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Patio
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West home for nine offers privacy right in the heart of all the action with amenities like a private hot tub and close proximity to the island's most notable attractions. You'll feel a sense of seclusion in this home, thanks to its location behind a charming gate and surrounded by lush...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    0.7 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • Parking
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking to show your family and friends a sunny getaway? Head to the Florida Keys with this two-bedroom, two-bathroom home on Key West with dog-friendly accommodations! Your home sits in a quiet neighborhood, not too far from shops and restaurants but far enough that your atmosphere is more...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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