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  • (305) 294-7358
Key West Time
October 22nd
9:17pm · 79°F

Cockadoodle Cottage On Duval ~ Weekly Rental

2BR 2BA ~ Weekly Rental
Sleeps 4-6

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.

Bedding Summary:

  • 1 king size bed
  • 1 queen size bed 
  • Each bedroom is a suite with its own en-suite luxury bath

Amenities: Upscale renovation and luxury furnishings. Fully equipped kitchen, central a/c, telephone, color cable TV, stereo, washer / dryer. Linens and towels are provided. Catering can be arranged. Maid service can be scheduled.

Activities: Elegant Upper Duval St. - Close to the Southern Most Point of the United States. South Beach is visible from your front porch so "mozy 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.

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.



Book Direct For The Best Price Guaranteed

Dates Weekly Nightly Terms
Oct 22, 2021 - Oct 31, 2021 $3340$572.757 night minimum
Nov 1, 2021 - Nov 6, 2021 $2265$437.004 night min. or 3 night min. 60 days prior to arrival.
Nov 7, 2021 - Nov 14, 2021 $2490$444.757 night minimum
Nov 15, 2021 - Nov 19, 2021 $2265$437.003 night minimum
Nov 20, 2021 - Nov 28, 2021 $2490$444.757 night min. or 3 night min. 60 days prior to arrival.
Nov 29, 2021 - Dec 17, 2021 $1895$419.754 night min. or 3 night min. 60 days prior to arrival.
Dec 18, 2021 - Dec 25, 2021 $3120$557.257 night minimum
Dec 26, 2021 - Jan 2, 2022 $3640$624.007 night minimum
Jan 3, 2022 - Jan 14, 2022 $2905$581.004 night min. or 3 night min. 60 days prior to arrival.
Jan 15, 2022 - Jan 21, 2022 $2905$560.254 night min. or 3 night min. 60 days prior to arrival.
Jan 22, 2022 - Jan 28, 2022 $2905$560.255 night minimum - 'within' Sat/Sat Only
Jan 29, 2022 - Feb 18, 2022 $3320$593.007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 19, 2022 - Feb 25, 2022 $3565$611.257 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 26, 2022 - Apr 17, 2022 $3320$593.007 night min Sat/Sat Only, but 3-5 nights within 60 days
Apr 18, 2022 - May 29, 2022 $3060$546.504 night min. or 3 night min. 60 days prior to arrival.
May 30, 2022 - Jun 10, 2022 $2955$570.004 night min. or 3 night min. 60 days prior to arrival.
Jun 11, 2022 - Aug 7, 2022 $3245$579.505 night min, but 3-4 nights within 60 days
Aug 8, 2022 - Sep 30, 2022 $2475$548.254 night min. or 3 night min. 60 days prior to arrival.
Oct 1, 2022 - Oct 20, 2022 $2955$570.004 night min. or 3 night min. 60 days prior to arrival.
Oct 21, 2022 - Oct 30, 2022 $4360$747.507 night minimum
Oct 31, 2022 - Nov 5, 2022 $2955$570.004 night min. or 3 night min. 60 days prior to arrival.
Nov 6, 2022 - Nov 13, 2022 $3245$579.507 night minimum
Nov 14, 2022 - Nov 18, 2022 $2955$570.003 night minimum
Nov 19, 2022 - Nov 26, 2022 $3245$579.507 night min. or 3 night min. 60 days prior to arrival.
Nov 27, 2022 - Dec 16, 2022 $2475$548.254 night min. or 3 night min. 60 days prior to arrival.
Dec 17, 2022 - Dec 25, 2022 $4065$726.007 night minimum
Dec 26, 2022 - Jan 2, 2023 $5935$1017.507 night minimum

Additional Notes:

  • High Season generally requires a 7 night minimum stay. Shorter stays of 3 - 5 nights may be available within 60 days of your arrival date or in special situations. Certain dates may not be available if they minimize optimal booking for the property's reservation calendar. Please contact us to inquire about stays less than 7 nights.
  • Shoulder and Low Season is a 3 - 5 night minimum available on reservations made within 60 days of arrival May through mid-August. From mid-August through mid-December, 3 - 5 night minimum stays are available any time.
  • Short Stays are available if there are open nights that are less than the minimum stay, shorter stays may be possible depending on the property. Please contact us to inquire.
  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 4th of July, Easter. A 7 night minimum stay is required for most major holidays, festivals, and events.

Rates and Terms are subject to change without notice. Above rates do not include taxes and fees. Click here for more details on additional fees. Please contact us for specific pricing and to confirm rates. Rates in US Funds. (305) 294-7358 Ext 1 -

Apply here for Travel Guard Trip Cancellation and Interruption Insurance.

VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.

  • 1 king size bed
  • 1 queen size bed. 
  • Each bedroom is a suite with its own en-suite bath.
Oct 13, 2021,
Loved the house and location. It was perfect for what we needed.

Mar 21, 2021,
Booked 1229 cottage last minute, interaction with agent and contract was quick and easy. Communication was thorough which made check in easy. Cottage was clean and as advertised. Had one issue with sink not draining and service was sent within the hour to fix the problem. Great cottage and KWVH service was great. Highly recommended.

Jan 20, 2021,
The house is clean and comfortable and the location is perfect. The end of Duval where the house is located is away from the hustle and bustle of the bars and restaurants at the other end, but within walking distance to all the things you want to see. Two blocks from the Southernmost Point and kitty-corner to the bus stop. The Duval Loop bus stop is free and runs about every 20-30 minutes. The house is close to at least three good places to get coffee and breakfast-two are literally four and five doors down. There is also a Starbucks at the beach two blocks down. Advice- rent bicycles. You can get them for $10/day. They are the best way to get around. Drivers are very careful around bikes and there are bike racks everywhere and they can be secured easily in the house’s fenced-in area. Fort Zachary Taylor is cool and has a nice beach. Bring water shoes if you are planning on going in. By noon you can always find live music downtown. The house’s porch is great for people watching.

Oct 22, 2020,

Jul 22, 2020,
The cottage was lovely. The location was perfect and your Custer service terrific. Thank you for a lovely vacation.

Jul 13, 2020,
Absolutely beautiful cottage and just as described. We totally enjoyed our vacation and will definitely use you again when we return.

Mar 20, 2020,
Cockadoodle Cottage in Old Town, Key West is perfect for a small family or two couples wanting a relaxing vacation with its updated and tasteful decor, comfortable beds, spacious bathrooms, kitchen and laundry amenities, and designated parking spot. During the busy season, make sure you bring earplugs for sleeping! The cottage is located at the corner of Duval and United Streets, a busy intersection for vehicles and pedestrians, which also means it is close to many nearby attractions and restaurants.

Jan 14, 2020,
The home was pretty and clean and in a perfect spot to explore Key West. Checking in was easy. The house was comfortable. The front porch is a great place to people watch and the back patio area is a wonderful place to grill, chat, and play games. We thoroughly enjoyed our stay.

Dec 20, 2019,
Ideal location for restaurants and bars, but far from the chaos. Clean and ample room. Lovely back patio.

Nov 23, 2019,
house was awesome, very clean but very noisy intersection, would recommend it to anybody.

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