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Cottages in Key West, FL

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    1 / 33
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 35
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 34
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 10
    4 of 5 bubbles (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Over 100 miles from mainland Florida and the southernmost point in the United States, Key West has attracted numerous artists and writers, including Ernest Hemingway, Wallace Stevens, Ralph Ellison, Elizabeth Bishop, Tennessee Williams, Robert Frost, and James Merrill. At 410 Caroline Street is... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed November 19, 2016
    This place was very nice and cozy just steps away from duval . Perfect for a quiet get away for you and/or your spouse . I've stayed many places and this one was just right for...
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    1 / 99
    4 of 5 bubbles (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed January 3, 2017
    This is a nice spot right of strip. Place is more for a family w young kids. Third bedroom is kinda small. Other than that place was real confronting. Enjoyed how close to...
    4 of 5 bubbles Reviewed November 9, 2015
    Enjoyed our stay here. Fairly sparse furnishings, but clean and functional. Location and price were the best points for this cottage. Short walk to everything, location is just...
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    1 / 32
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    'Simonton Court Cottages' consists of the 4 nightly units 'Audubon House,' 'Truman Efficiency,' 'Monroe Efficiency,' and 'Mallory Efficiency.' In total, this group rental sleeps 8 - 10 comfortably. Perfect for cost-conscious, larger, groups who are looking for great a location. Take advantage of... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    3.5 of 5 bubbles (3) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Part of TROPICAL VILLAGE Southern Cross: Lounging next to the gorgeous shared pool or sitting in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed April 21, 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information. I did not stay in this particular cottage but our guests had rave...
    5 of 5 bubbles Reviewed October 7, 2014
    The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15 minute...
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    1 / 16
    4.5 of 5 bubbles (49) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed October 19, 2016
    Returning to Ann Street. Such a comfortable bed!! We love the little Ann Street compound with its secluded pool and lush gardens. Tranquility was the perfect size for us two...
    4 of 5 bubbles Reviewed September 19, 2013
    Owners were unbelievably nice from the beginning of communication with them! This cottage lives up to its name. I'm pretty sure the maid skips the bathroom when she cleans in...
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    1 / 41
    5 of 5 bubbles (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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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,... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed April 23, 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...
    5 of 5 bubbles Reviewed July 2, 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 however...
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    1 / 33
    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 24 | Quick View
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    • Satellite TV
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    • x
    About this property
    Southernmost Sanctuary Suites are comprised of the following homes Egret Suite, Heron Suite, Ibis Suite, Osprey Suite, Pelican Suite, Seagull Suite which can all be booked individually. Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed May 26, 2016
    Was a bit frustrated after arriving to realize the office that rents these was not on site but at 1075 duval suite 22..I had booked through booking. Com and at first they couldn't...
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    1 / 28
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
    About this property
    The house is a traditional Key West cottage that has undergone a complete renovation in 2012. The charm and historic features have been retained, while all the luxuries of today have been added. There is a master bedroom, with king bed and full bath, on the first floor. Additionally, there is a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed December 3, 2016
    Very nice clean Bungalo. Close to Dival walking distance from everything In old town. My only minor complaint is that the barbecue pit was absolutely filthy. I spent a lot of...
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    1 / 15
    4.5 of 5 bubbles (47) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Patio
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    • x
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    • x
    About this property
    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer.... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed July 2, 2013
    I selected this cottage via computer. The location is excellent for seeing ALL the sights of Key West. This cottage is as represented. The kitchen was spacious and nicely...
    5 of 5 bubbles Reviewed August 1, 2012
    The location is excellently placed in Key West. My girlfriend and I were never more than a 15 minute walk to anything that we needed and the kitchen had many of the things we...
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    1 / 21
    1 of 5 bubbles (1) Terrible
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Porch
    • DVD Player
    • Balcony
    • Air Conditioning
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back to Key West. As... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This newly renovated unit is located just two blocks from world famous Duval Street surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway. The bungalow features an one level open space living/dining area, full kitchen and a spacious... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • x
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    About this property
    28 Night Minimum - Monthly Rentals Only Can you say “perfectly adorable”? We thought so. Now picture “perfectly adorable” and you have found Poppy. Poppy is a one-bedroom, one-bath home that is perfect for one or a couple. The front porch is perfect for people watching and chatting with locals... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • x
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    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed August 2, 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 is...
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    1 / 26
    5 of 5 bubbles (21) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Yard
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    • Pet-friendly
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    • x
    • x
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    About this property
    Romantic, Private, Boutique Guesthouse with only 2 suites in Key West, Florida steps away from the Beach and Ocean and the Key West Wildlife Center. Reserve 1 room for a couple or both rooms to accommodate up to 4. The owners Capt. Steve and Kayla offer Snorkeling, Sunset trips, eco-adventure... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed December 17, 2015
    My husband and I stayed with Kayla and Steve for five days and it was the most relaxing fun filled stay ever. The accommodations were very clean and our hosts were the...
    5 of 5 bubbles Reviewed February 12, 2015
    Atlantis House is a very special hideaway. It is called a guest house, and we were truly the guests of Steve and Kayla. They were so welcoming from the day we arrived: helping...
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    1 / 25
    4.5 of 5 bubbles (52) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
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    • x
    About this property
    REDUCED MINIMUM NIGHT STAYS for March! (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed August 15, 2016
    I honestly hesitated to write this review because I want to keep it all to myself. My husband and I are unwilling transplants, having lived in Key West until about 6 years...
    5 of 5 bubbles Reviewed July 26, 2016
    Key West was a bucket list trip for my husband & I. It was perfect!! Tim with Historic Hideaways was wonderful in making this an unforgettable trip. We've decided we will be back...
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    1 / 22
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Key West, Florida Keys 33040
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • x
    Location Information
    Key West, Florida Keys 33040
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    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Key West, Florida Keys 33040
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Key West, Florida Keys 33040
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    Key West, Florida Keys 33040
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Key West, Florida Keys 33040
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Key West, Florida Keys 33040
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Key West, Florida Keys 33040
    1 / 15
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    Key West, Florida Keys 33040
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. <BR><BR>Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Key West, Florida Keys 33040
    1 / 22
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    Key West, Florida Keys 33040
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Key West, Florida Keys 33040
    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Key West, Florida Keys 33040
    1 / 6
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Key West, Florida Keys 33040
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Key West, Florida Keys 33040
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
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    Key West, Florida Keys 33040
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Key West, Florida Keys 33040
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Key West, Florida Keys 33040
    1 / 33
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
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    • x
    About this property
    Beautifully renovated cozy cottage in the heart of Key West!  Everything you dream about when “Key West cottage” comes to mind!  A true, original Key West cottage that features a wonderful covered front porch so you may enjoy cocktails or people-watching and tons of other outdoor amenities... View all property information
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    Key West, Florida Keys 33040
    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Ocean Views
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    • Waterfront
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    • Pet-friendly
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    • x
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    • x
    About this property
    Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner JennAir cook top, dishwasher, under counter refrigerator, microwave and everything you need to prepare meals. We also provide plastic wrap, foil, ziplock bags…and coffee, cream... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Part of 4 exclusive units at Abbey Road, McCartney's Manor is in a private, gated compound. The state-of-the-art kitchen includes granite counter tops, a Jenn-Air 2 burner cook top, dishwasher, under counter refrigerator, microwave, coffee maker, toaster, blender and soft mood lighting under and... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Children's Pool
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    About this property
    Part of 4 exclusive units at Abbey Road in a private, gated compound just off Duval Street The original Cuban tile has been preserved throughout the house to make it very unique. Upon entering the spacious living room, a large tropical sectional queen sleeper sofa, with Memory Foam mattress,... View all property information
    Location Information
    Key West, Florida Keys 33040
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