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Holiday Rentals 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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    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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    0.4 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    0.4 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Duval Sea Turtle1 / 24
    (49)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2016
    Just returned from a stay and this property exceeded our expectations. It was a great location in easy walking distance to everything on Duval. The unit was spotlessly clean...
    Reviewed 5 July 2014
    Great Location to enjoy all Key West has to offer. CVS for stocking up on snacks, alcohol, basic groceries is right next door. It was great to have 2 baths upstairs and 1/2 down...
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    About this property
    DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire Key West rental property has been decorated using art from the local galleries and artists. The theme is 'Key West' from scenes around the...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ecco Domani1 / 24
    (1)Excellent
    0.5 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ECCO DOMANI – Ecco Domani means 'Here Tomorrow' which is where you'll want to be when you see what you're missing. A beautiful 3 story home with private pool, off street parking and attractive appointments -- a wonderful Key West escape that you will want to come home to year after year. Enter...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Island Wind1 / 46
    (10)Excellent
    0.5 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 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...
    Reviewed 5 December 2013
    Enjoyed Thanksgiving week here. Island Wind is in a perfect location. It is an easy walk to the southern most beach & a doable walk to Mallory Square. Duval is only a...
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    About this property
    ISLAND WIND : Welcome to a tropical sun drenched oasis in the heart of Old Town Key West. This charming 2 bedroom 2 bath Bahamian style townhome, with tin roof and white spindled decks reminiscent of old Key West, is located in award winning Windward Park, a gated and secure compound consisting...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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 12 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 2 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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    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 12 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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    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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    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 27 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 31 August 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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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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 2 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 9 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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    Dog-friendly home w/ private pool - walk to the beach and restaurants!1 / 27
    (1)Excellent
    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Terrace
    • Washer
    • Balcony
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2018
    Had a great surprise birthday weekend in Key West. The house was fantastic! Very clean and bigger than the pictures make it seem. Loved the heated pool, and close walk to Duval...
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    About this property
    Escape to the Florida Keys for a relaxing vacation in this three-bedroom, two-and-a-half bath home for eight (six comfortably) with a private pool and walking distance to the beach and Duval Street. And your favorite canine friend is also welcome for a small nightly fee. This rental is mere blocks...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    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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    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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    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
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 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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    Leeward Isle Key West Retreat1 / 24
    (35)Very good
    0.5 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Terrace
    • Air Conditioning
    • Parking
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 January 2014
    We have rented in the Windward Park before, but this unit was the nicest unit by far. Recently updated and remodeled. Completely supplied with anything you will need.
    Reviewed 20 November 2013
    We just love this little get away home that we get to stay at when in Key West. The new owners have done a nice job of re-modeling and the Leeward Isle is so comfortable.
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    About this property
    LEEWARD ISLE KEY WEST RETREAT -- Dwell in the possibility! From the moment you park in the private parking lot for this Key West vacation condo you know you are someplace special. A small gated and secured compound with only 13 properties, this townhome community is quiet and private while still...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Twice as Nice ~ Weekly Rental1 / 34
    (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 31 August 2017
    Great houses in a perfect location. Everything was very clean and to the highest standard. Easy to book. Highly recommended.
    Reviewed 27 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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    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 16 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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    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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    Duval Breeze1 / 24
    (56)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2015
    First off At Home in Key West is awesome. We have used them twice and never had any trouble at all. They are very prompt, courteous and a delight to deal with. The condo...
    Reviewed 26 February 2014
    Loved Duval Breeze! The house was bigger than the pictures depicted and it was so comfortable. Having not only towels and linens available but also basics like toilet paper...
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    About this property
    DUVAL BREEZE: Enjoy the great location of this beautiful 2 bedroom 2.5 bath vacation home key west located in the gated rooftop community of Duval Square on Duval Street, in the middle of the action. Steps away from fantastic restaurants, nightlife, entertainment, bars and shopping on Duval...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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
    5 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    • Grill
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This family-friendly Key West home features five separate villas grouped together, a shared pool, and a location that puts you close to all of the action. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am Located on Center Street, this home is just a mile from the Key West...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 20
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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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    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • DVD Player
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 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 29 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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    Tropical Dreaming1 / 24
    (58)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 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 21 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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    Bella Vita1 / 22
    (6)Very good
    0.2 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The rental was in a great location and the bed was comfortable. However, the ceilings were super thin and we could hear people walking around above us all night, even with a fan...
    Reviewed 8 January 2018
    Being just steps from Duval made this the perfect place to head out to tour the town. We were delighted with Bella Vita became it was exactly as represented on website. We found...
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    About this property
    Cozy, comfortable, affordable. Not to mention a location in the very heart of the Historic District of Upper Duval. That's why this one bedroom/one full bath rental is aptly named Bella Vita, the beautiful life. Located within La Casa de Luces building, Bella Vita features a wrap-around porch, a...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    0.2 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This dog-friendly suite provides everything you need for a couple's getaway in Key West. This home's coveted location on Duval Street means prime access to the town's best nightlife and restaurants, like Nine One Five a few blocks away. You're also a short walk from the beach here: Southernmost...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Vintage Luxury Cottage ~ Weekly Rental1 / 44
    (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 4 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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    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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    Spa On Duval1 / 24
    (5)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2014
    My family found this place amazingly comfortable and exactly what we needed. Our two teenagers loved the place. It was so nice and close to downtown one way, and up to the...
    Reviewed 7 August 2013
    Let me first write that we've stayed in the duval complex before in the havana hideaway unit( great unit!) Spa on duval was very clean, great location and equipped with...
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    About this property
    SPA ON DUVAL - Is a tropical two story, 2 bedroom 2.5 bath Old Town Key West condo located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants, speciality shops and the action of Duval Street. Spa On Duval is truly a Key West experience to enjoy!...
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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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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • DVD Player
    • Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shrimp Party (MONTHLY RENTAL): Key West Pinks, parties and drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway to Key West is just not enough, pack your extra gear and settle in for the month or longer. A tropical getaway located in the heart of Old...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    • Hot Tub
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 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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    0.5 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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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    0.3 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grab your sunglasses, your beach towel, and charge your camera for a visit to this Key West home, once the winter home of Pulitzer Prize-winning cartoonist Jeff MacNelly. Offering a family-friendly atmosphere and a pristine shared pool, this home gives you the chance to experience the best of...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 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 12 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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    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Internet Access
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the allure of old town Key West at this dog-friendly condo, where you'll have a private hot tub and deck, a community swimming pool, and enviable access to beaches, shops, and wonderful restaurants. Located mere steps from Duval Street and verdant tropical gardens, this Duval Square condo...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.2 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Internet Access
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in style in the heart of Key West, where your balcony overlooks the colorful main drag! This home has dog-friendly accommodations for a small nightly fee. This condo faces historic Duval Street, where you'll find some of Key West's most exciting shopping and dining. Walk three blocks to the...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Treat the whole family to a seaside adventure when you book your getaway to this dog-friendly Key West cottage. Boasting a prime location close to beach activities and attractions, as well as a shared pool, this home welcomes up to six guests and a canine companion (for a small nightly fee). This...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.1 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Settle in at this conveniently located four-person suite, where you'll have access to a shared hot tub and your own kitchenette! Egret Suite can be rented on its own, or as a part of the entire property for larger groups. The family dog is also welcome to join you for an additional nightly fee. At...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    0.5 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Parking
    • Washer
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This dog-friendly Key West gem offers a palm-covered patio and grill area, a kitchenette, free WiFi, and street parking! Plus, you're walking distance from the beach, historic landmarks, and local dining. Walk a half mile to the beach and enjoy Key West's legendary white sand and turquoise water!...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    0.4 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Parking
    • Terrace
    • Air Conditioning
    • Balcony
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the beachy retreat you've been searching for at this dog-friendly Key West condo, where you'll enjoy a private balcony, a shared swimming pool, and a wonderful location for exploring. Beautifully positioned to overlook the gardens of Duval Square, this condo offers guests unbeatable...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.3 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from the stress of the daily grind with a trip to this contemporary Key West home. Offering street parking, access to a shared pool, room for up to four guests, and a charming island-themed ambiance, this home will make it easy to slip into vacation mode. The family dog is also welcome to...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.5 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two-bedroom, one-bathroom house is the perfect place for your next family vacation to the palm-tree paradise of Key West! With a great location downtown, a private parking space, and easy access to a sandy beach nearby, you'll be all set for fun in the sun. Located a half block from bustling...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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
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    • 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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    0.2 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan a romantic getaway for two to Key West at this quaint studio rental complete with a well-equipped kitchenette, furnished patio, and access to a shared swimming pool, well-maintained tropical courtyard, and sundeck. This complex is located in a quiet, residential neighborhood and there is...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    0.5 kilometres from Southernmost Point
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Parking
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A large group getaway to Key West starts with this pair of charming cottages, which feature a total five bedrooms, three-and-a-half bathrooms, and a max occupancy of 16. The property also includes a private heated swimming pool, a private hot tub, and dog-friendly accommodations. The cottages sit...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
    • Parking
    • Balcony
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Surround yourself with the historic charms of Key West at this dog-friendly penthouse, a spacious South Florida escape with a private hot tub, a deck and balcony for evening cocktails, and access to a lovely community swimming pool. You'll find this comfortable condo in Duval Square, offering...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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