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 Cottage vacation rental has been recreated, redesigned, adapted and reformed, reflecting the ever-changing yet ever-inspired persona of the enchanted island of Key West.
Key West Culture: Like most historic Key West houses, over the course of 100 years this special little gem-of-a-cottage has been home to many different island dwellers - most of whom were "regular residents" - but some who were down-right colorful... and infamous! If you've visited Key West within the last five years or so, you know what I'm talking about and will definitely recall that until the most recent major makeover of this charming cottage - it was famously known and operated for awhile as The Chicken Store. And indeed it was at one time the home of the Rooster Rescue Team (RRT), a volunteer group devoted to preserving some of Key West's more notorious cackling cockadoodling dwellers - orphaned and wounded gypsy chickens who previously wandered the streets. When some Key West "newcomers" tried to ban chickens from the island, the RRT stepped in to defend them... and put them up for adoption!
Then in the year 2007, change was in the air in a big way! The Chicken Store, and it's intire mission, was moved off Duval Street to an appropriate country-side location. At last, the rescued can safely roam free under the care of their devoted guardians awaiting new homes.
A New Beginning: Once the chickens were moved, the cottage was given a stunning transformation. Architectural plans and building preparations were made to completely remake the cottage to meet first-class accommodation standards. In homage to its past, it was humously named the Cockadoodle Cottage! Renovations and design were done to match the twin-cigar cottage next door, known as, Havana Moon. The finished renovation created a unique layout - making it possible for the two cottages to function either separately or together as Twice As Nice on Duval Street!
Keeping with moden minimalist renovation design and decorum, that is set in the Havana Moon cottage, this Cockadoodle Cottage is also appointed with modern island furnishings and art work. The floorsare tiled throughout this cottage, using a soft earth-tone. High ceilings and recessed lighting give the rooms a more spacious feeling. Even though the interior is completely re-mastered to make two luxurious bedroom suites, a full kitchen, and master bath with Jacuzzi tub, the owner retained the original interior structure enough so that you can still enjoy the authentic flavor of the single "shot-gun" design. The classic "shot-gun" layout of the cottage essentially mirrors its twin, the Havana Moon cottage.
Cottage Layout: We can begin our description of the Key West Cockadoodle Cottage at the front entrance which is set to the left of the front of the house. Upon entering the front door you step immediately into the common "hall room" that heads straight away to the back door. Off this main common room, on the left side of the house, a symmetrical row of interior rooms proceed from the front of the cottage to the back.
The first door on your left leads to the front bedroom and beautiful en-suite bathroom. The front bedroom is elegant and luxurious and provides a queen bed. Furnishings are tasteful and elegant.* (see notes)
The next room is a brand-new modern "U-shaped kitchen," complete with top-of-the-line appliances and recessed lighting. The kitchen is open to the wide "sitting hall" which at this point becomes the interior gathering and common seating space for the cottage.
The last room down the hall at the back of the house is the spacious back bedroom and en-suite bathroom with Jacuzzi bath tub. The back bedroom suite offers a king size bed and is appointed with beautiful bedding and furnishings. At the end of the hall the back door opens to the small back porch.
Back outside and around to the front of the cottage, is the covered front sitting porch where you can catch a view of the ocean and a soft salt southern breeze. Pretty wicker furnishings have been placed for guests to sit and watch the world of Key West go by.
Amenities: Upscale renovation and luxury furnishings. Fully equipped kitchen, central a/c, telephone, color cable TV, stereo, washer / dryer. Linens and towels are provided.
Activities: Elegant Upper Duval St. - Close to the Southern Most Point of the United States. South Beach is visible from your front porch so "mosey on over" for some sun and good food. There is a great open air beach side restaurant there with a full bar and excellent beach side menu. Cafe neighborhood features art galleries, wonderful eateries and internationally famous fine restaurants, fine gift and clothing stores, Grand Vin wine tasting, home made ice cream. Here you start at the top of Duval St. near the Atlantic Ocean and can take the 20 min "Duval Crawl" to the Gulf of Mexico (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife. Come breakfast time, you will be literally steps away from fresh-baked delicacies at two great pâtisseries- La Grignote at the end of your block, and Frenchie's Cafe right around the corner.
Area: Upper Duval or ‘Uptown Key West’ has evolved into the “elegant end of Duval” and offers an exceptional variety of restaurants, beautiful boutiques, and art galleries. Close enough to South Beach that you can see it from the porch and the Southernmost Point of the United States, is just around the corner. Walk to Mallory Square Sunset Celebration in 15 to 20 minutes.
Parking: There is off-street parking for one full size car, but from here you really never need to get in your car. Upper Duval Street is right out your front door, so forget the hassle of parking and enjoy walking or biking everywhere. Enjoy the island to the fullest.
Restrictions: Smoke free house. Smoking permitted outside only. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. As with all private vacation homes, occupants of this property must adhere to the Sound Control / Noise Ordinance of Key West - ARTICLE IV Sec. 26-191. Absolutely no pets please.
*Notes: This property is ideal for couples, professionals, executives, and families who have discerning tastes looking for a luxurious accommodation. This cottage may not be appropriate for children due to its location. Please contact us for more information.If you love this cottage and are interested in having access to the swimming pool, it is possible to rent the twin-cottages together by including the Havana Moon cottage. Please see description of this twin-layout in our Key West Villa section where the property is identified as Twice As Nice.
|Nov 28, 2023 - Dec 16, 2023||$2265||$501.75||4 night min. or 3 night min. 60 days prior to arrival.|
|Dec 17, 2023 - Dec 25, 2023||$3790||$677.00||7 night min. or 3 night min. 60 days prior to arrival.|
|Dec 26, 2023 - Jan 2, 2024||$4420||$757.75||7 night minimum|
|Jan 3, 2024 - Jan 12, 2024||$3300||$635.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Jan 13, 2024 - Jan 19, 2024||$3300||$635.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Jan 20, 2024 - Feb 2, 2024||$3300||$635.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Feb 3, 2024 - Feb 16, 2024||$3780||$725.00||5 night min, but 3-4 nights within 60 days|
|Feb 17, 2024 - Feb 23, 2024||$4050||$775.00||5 night min, but 3-4 nights within 60 days|
|Feb 24, 2024 - Apr 12, 2024||$3780||$725.00||5 night min, but 3-4 nights within 60 days|
|Apr 13, 2024 - May 29, 2024||$2995||$575.00||4 night min. or 3 night min. 60 days prior to arrival.|
|May 30, 2024 - Jun 9, 2024||$2695||$535.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Jun 10, 2024 - Aug 11, 2024||$2995||$575.00||5 night min, but 3-4 nights within 60 days|
|Aug 12, 2024 - Oct 2, 2024||$2095||$475.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Oct 3, 2024 - Oct 17, 2024||$2225||$515.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Oct 18, 2024 - Oct 27, 2024||$4055||$725.00||7 night minimum|
|Oct 28, 2024 - Nov 3, 2024||$2695||$520.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Nov 4, 2024 - Nov 11, 2024||$2995||$535.00||7 night minimum|
|Nov 12, 2024 - Nov 21, 2024||$2695||$520.00||3 night minimum|
|Nov 22, 2024 - Nov 30, 2024||$2995||$535.00||7 night min Sat/Sat Only, but 3-5 nights within 60 days|
|Dec 1, 2024 - Dec 16, 2024||$2265||$485.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Dec 17, 2024 - Dec 25, 2024||$3975||$765.00||7 night minimum|
|Dec 26, 2024 - Jan 2, 2025||$4640||$890.00||7 night minimum|
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|Jan 11, 2025 - Jan 17, 2025||$0||$0.00|
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|Oct 2, 2025 - Oct 16, 2025||$0||$0.00|
|Oct 17, 2025 - Oct 25, 2025||$0||$0.00|
|Oct 26, 2025 - Nov 2, 2025||$0||$0.00|
|Nov 3, 2025 - Nov 10, 2025||$0||$0.00|
|Nov 11, 2025 - Nov 20, 2025||$0||$0.00|
|Nov 21, 2025 - Nov 28, 2025||$0||$0.00|
|Nov 29, 2025 - Dec 16, 2025||$0||$0.00|
|Dec 17, 2025 - Dec 25, 2025||$0||$0.00|
|Dec 26, 2025 - Jan 2, 2025||$0||$0.00|