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  • (305) 294-7358
Key West Time
December 17th
9:20am · 63°F

Cockadoodle Cottage ~ 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!

Well, in the year 2007, change was one once again in the air, it was time for The Chicken Store to move along to a new home. Now don't fret chicken lovers - the entire contents and mission of The Chicken Store were moved off Duval Street to a larger and more appropriate country-side location where the rescued chickens now safely roam free under the care of their devoted guardians awaiting new homes.

A New Beginning: The family that owns the cottage has had it in their family for generations and once they reclaimed it, they gave it a loving and stunning transformation. New architectural plans and building preparations were immediately made to completely remake the cottage to meet first-class accommodation standards of its twin-cigar cottage next door known as, "Havana Moon." So in January 2008 the latest renovation began to compliment its next-door twin, striving to balance the new layout making it possible for the two cottages to function either separately or together as one - equally as well.

Keeping with the romantic minimalist renovation design and decorum, that is set in the Havana Moon cottage, this cottage is also appointed with classic island furnishings, subtle colors and quiet artwork to set a tone of calmness and relaxation. The floors have been 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 "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.

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.


special rates available

Jan 5- Jan 8
Jan 20- Jan 24
Nightly $400

view all specials

Dates Weekly Nightly Terms
Nov 24, 2018 - Dec 19, 2018 $1700$4003 night minimum
Dec 20, 2018 - Dec 28, 2018 $2650$5007 night minimum
Dec 29, 2018 - Jan 4, 2019 $3225$5007 night minimum
Jan 5, 2019 - Jan 11, 2019 $2100$5004 night min. or 3 night min. 60 days prior to arrival.
Jan 12, 2019 - Jan 18, 2019 $2300$5004 night min. or 3 night min. 60 days prior to arrival.
Jan 19, 2019 - Jan 25, 2019 $2300$5004 night min. or 3 night min. 60 days prior to arrival.
Jan 26, 2019 - Feb 1, 2019 $2300$5005 night minimum - 'within' Sat/Sat Only
Feb 2, 2019 - Feb 15, 2019 $2650$5007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 16, 2019 - Feb 22, 2019 $2850$5007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 23, 2019 - Apr 19, 2019 $2650$5007 night min Sat/Sat Only, but 3-5 nights within 60 days
Apr 20, 2019 - May 26, 2019 $2250$4004 night min. or 3 night min. 60 days prior to arrival.
May 27, 2019 - Jun 14, 2019 $2025$4004 night min. or 3 night min. 60 days prior to arrival.
Jun 15, 2019 - Aug 8, 2019 $2250$4004 night min. or 3 night min. 60 days prior to arrival.
Aug 9, 2019 - Oct 19, 2019 $2025$4003 night minimum
Oct 20, 2019 - Oct 26, 2019 $3000$5007 night minimum
Oct 27, 2019 - Nov 3, 2019 $2025$4003 night minimum
Nov 4, 2019 - Nov 10, 2019 $2250$4007 night minimum
Nov 11, 2019 - Nov 22, 2019 $2025$4003 night minimum
Nov 23, 2019 - Nov 29, 2019 $2250$4007 night minimum
Nov 30, 2019 - Dec 20, 2019 $1700$4003 night minimum
Dec 21, 2019 - Dec 27, 2019 $2800$5007 night minimum
Dec 28, 2019 - Jan 3, 2020 $3275$5007 night minimum
Jan 4, 2020 - Jan 10, 2020 $2150$5004 night min. or 3 night min. 60 days prior to arrival.
Jan 11, 2020 - Jan 17, 2020 $2350$5004 night min. or 3 night min. 60 days prior to arrival.
Jan 18, 2020 - Jan 24, 2020 $2350$5004 night min. or 3 night min. 60 days prior to arrival.
Jan 25, 2020 - Jan 31, 2020 $2350$5005 night minimum - 'within' Sat/Sat Only
Feb 1, 2020 - Feb 14, 2020 $2700$5007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 15, 2020 - Feb 21, 2020 $2900$5007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 22, 2020 - Apr 18, 2020 $2700$5007 night min Sat/Sat Only, but 3-5 nights within 60 days
Apr 19, 2020 - May 25, 2020 $2250$4004 night min. or 3 night min. 60 days prior to arrival.
May 26, 2020 - Jun 13, 2020 $2025$4004 night min. or 3 night min. 60 days prior to arrival.
Jun 14, 2020 - Aug 7, 2020 $2250$4004 night min. or 3 night min. 60 days prior to arrival.
Aug 8, 2020 - Oct 18, 2020 $2025$4003 night minimum
Oct 19, 2020 - Oct 25, 2020 $3050$4007 night minimum
Oct 26, 2020 - Nov 2, 2020 $2025$4003 night minimum
Nov 3, 2020 - Nov 9, 2020 $2250$4007 night minimum
Nov 10, 2020 - Nov 21, 2020 $2025$4003 night minimum
Nov 22, 2020 - Nov 28, 2020 $2250$4007 night minimum
Nov 29, 2020 - Dec 19, 2020 $1700$4003 night minimum
Dec 20, 2020 - Dec 26, 2020 $2850$5007 night minimum
Dec 27, 2020 - Jan 2, 2021 $3325$5007 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, New Years, Key West Yacht Race Week, Thanksgiving, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, Biker's Poker Run, 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.
Nov 04, 2018,
The Cockadoodle cottage was awesome! Very clean and well stocked. Very responsive and helpful during all interactions.

Mar 09, 2018,
The Cockadoodle Cottage was well equipped and located where it was convenient to either walk, rent bikes or hop on the free Duval Loop bus!! The beach is a block away with a great cafe and bar!! I would highly recommend for two adult couples to stay here!!

Feb 21, 2018,
Location is wonderful! Across from the new Duval loop free bus which took us from the south end to the north end conveniently. Unit was clean, well equipped and beds were super comfortable. We did utilize the parking space outback and that was helpful. The banana Café was great for breakfast, we really enjoyed the 915 restaurant as well. Our first night there we went down to the rum bar and that was great too.

Feb 19, 2018,
Great experience! Staff was more than helpful. Booking next year’s vacation with them again. Highly recommend.

Feb 19, 2018,
Great place to stay.

Jan 20, 2018,
We enjoyed staying at cock a doodle cottage. A cute little cottage with all the amenities. On Duvall St. with easy walking distance to all the goings on. We would definitely stay there again.

Aug 08, 2017,
Home was nice. A few small issues here and there but nothing a homeowner would not expect of their own home. Great location for beaches. A bit noisy at is on a very popular corner for foot traffic.

Apr 06, 2017,
We had a great stay in Key West. We stayed at the Cockadoodle Cottage which was very clean and up-dated. Spectacular experience. Highly recommend staying there and will be planning another trip next year. Also had a great experience with the staff who works for Vacation Homes. Thanks for a wonderful vacation.

Feb 23, 2017,
We had a lovely time and cottage was very comfortable and attractive. There were 4 in our party and we all had plenty of room. The location at the south end of Duval St. was convenient to attractions and restaurants and not quite as noisy as further up the street.

Feb 07, 2017,
Great location and lots of fun!!!

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