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  • (305) 294-7358
Key West Time
July 12th
10:00am · 87°F

Cockadoodle Cottage On Duval ~ Weekly Rental

2BR 2BA ~ Weekly Rental
Sleeps 4

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, smart TV, 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.

Payment by credit card will be subject to 3.85% surcharge.



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special rates available


July 15 - Aug 12

Nightly $450
Weekly $1900

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Dates Weekly Nightly Terms
Jun 10, 2024 - Aug 11, 2024 $2695$535.004 night min. or 3 night min. 60 days prior to arrival.
Aug 12, 2024 - Oct 2, 2024 $2095$475.004 night min. or 3 night min. 60 days prior to arrival.
Oct 3, 2024 - Oct 17, 2024 $2225$515.004 night min. or 3 night min. 60 days prior to arrival.
Oct 18, 2024 - Oct 27, 2024 $4055$725.007 night minimum
Oct 28, 2024 - Nov 3, 2024 $2695$520.004 night min. or 3 night min. 60 days prior to arrival.
Nov 4, 2024 - Nov 11, 2024 $2995$535.007 night minimum
Nov 12, 2024 - Nov 21, 2024 $2695$520.003 night minimum
Nov 22, 2024 - Nov 30, 2024 $2995$535.007 night minimum
Dec 1, 2024 - Dec 18, 2024 $2265$485.004 night min. or 3 night min. 60 days prior to arrival.
Dec 19, 2024 - Dec 27, 2024 $3975$765.007 night minimum
Dec 28, 2024 - Jan 3, 2025 $4640$890.007 night minimum
Jan 4, 2025 - Jan 10, 2025 $3420$660.004 night min. or 3 night min. 60 days prior to arrival.
Jan 11, 2025 - Jan 17, 2025 $3420$660.004 night min. or 3 night min. 60 days prior to arrival.
Jan 18, 2025 - Jan 31, 2025 $3420$660.004 night min. or 3 night min. 60 days prior to arrival.
Feb 1, 2025 - Feb 14, 2025 $3900$750.005 night min, but 3-4 nights within 60 days
Feb 15, 2025 - Feb 21, 2025 $4170$800.005 night min, but 3-4 nights within 60 days
Feb 22, 2025 - Apr 11, 2025 $3900$750.005 night min, but 3-4 nights within 60 days
Apr 12, 2025 - May 28, 2025 $2995$575.004 night min. or 3 night min. 60 days prior to arrival.
May 29, 2025 - Jun 8, 2025 $2695$535.004 night min. or 3 night min. 60 days prior to arrival.
Jun 9, 2025 - Aug 10, 2025 $2695$535.004 night min. or 3 night min. 60 days prior to arrival.
Aug 11, 2025 - Oct 1, 2025 $2095$475.004 night min. or 3 night min. 60 days prior to arrival.
Oct 2, 2025 - Oct 16, 2025 $2225$515.004 night min. or 3 night min. 60 days prior to arrival.
Oct 17, 2025 - Oct 25, 2025 $4055$725.007 night minimum
Oct 26, 2025 - Nov 2, 2025 $2695$520.004 night min. or 3 night min. 60 days prior to arrival.
Nov 3, 2025 - Nov 10, 2025 $2995$535.007 night minimum
Nov 11, 2025 - Nov 20, 2025 $2695$520.004 night min. or 3 night min. 60 days prior to arrival.
Nov 21, 2025 - Nov 29, 2025 $2995$535.007 night min. or 3 night min. 60 days prior to arrival.
Nov 30, 2025 - Dec 19, 2025 $2265$485.004 night min. or 3 night min. 60 days prior to arrival.
Dec 20, 2025 - Dec 27, 2025 $4095$790.007 night minimum
Dec 28, 2025 - Jan 5, 2026 $4760$815.007 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.
Nov 20, 2023,
VHKW was great to work with. I appreciate the ease of renting the house and the communication with VHKW regarding checkin and check out. I’d definitely rent from VHKW again.

Aug 14, 2023,
Very helpful with suggestions and very helpful with any issues. Had a wonderful yime

Jun 01, 2023,
Nice stay. Location was great on the quiet end of Duval. Nice restaurants nearby - we really enjoyed Frenchie’s on United. Everything is walking distance but we did drive to Fort Zachary Taylor beach. It was our favorite beach during our stay. The cottage is dated but cute. 2 bedrooms with an en-suite bathroom in each. I didn’t use the shower in the main because the water pressure was not great. The washer and dryer came in handy for the beach towels, which were provided. Traffic noise and roosters crowing but these didn’t bother us. For a bit of added color, there is a “gentlemen’s club” a few doors down on Duval but we (or at least, I) never saw or heard anything untoward. Right down the street from the butterfly conservatory. Relaxing vacation and would stay here again.

Mar 09, 2023,
Duval street house was as described and in a very good location.

Feb 15, 2023,
This is the second year in a row that we stayed at the Cockledoodle Cottage. Easy check in, very clean, great location.

Jul 19, 2022,
We booked Cockadoodle cottage and had a lovely time. The location was excellent. The house was perfectly equipped and comfortable. I must say the the best part of the experience was booking the property and interfacing with the management company. The main reason for this was Anastasia! WOW! What a pro! Anastasia went above and beyond to make the reservation and stay seamless and very pleasant. VHKW is the quintessential authority on all things Key West and their properties are exceptional! Make sure you ask to work with Anastasia! You won’t be disappointed! Thanks. See you again soon.

Apr 12, 2022,
Great house and great location! House was clean and tidy. I wish the pillows in the back bedroom were a little fluffier, but that’s a personal preference. Also, if you are short with short legs, getting in and out of the shower can be a challenge. I’ve stayed in many different houses around Key West, and this one ranks up there with the best. Surprisingly, the neighborhood was noiser that I thought it would be, but it didn’t really bother us. We’ll definitely keep this one in our rotation.

Apr 03, 2022,
Fantastic time. Great cottage. Great location. The house was cozy and clean. Everything was perfect.

Mar 02, 2022,
Cockadoodle Cottage was great location. Convenient, to lots of stuff and fun place on duval. The only issue was the furniture on the back porch needs to be replaced. It was very unstable and looked like it had been fixed several times. My husband sat in one and it fell apart sending him to the ground with a busted elbow. We called and let your office know.

Feb 24, 2022,
The cottage was immaculate and in a great location. When our first reservation was cancelled by the owner, VHKW found us a replacement and made the transition easy!

Feb 16, 2022,
The house was very nice, great location. The back bedroom bed was uncomfortable for my wife and the bathtub/shower was difficult to get in and out of. Other than that, had a enjoyable time at this property.

Feb 15, 2022,
Our visit was smooth. The property was as represented, had adequate supplies and check out was easy. We will use your rental services in the future!

Feb 09, 2022,
We really liked the place we stayed in. We would recommend it to anyone and we want to stay in it again next year and possibly rent the adjoining house as well

Jan 30, 2022,
We had another great stay. The house is clean and comfortable, as always. The new rocking chairs for the porch are nice, but just a bit too large for the width of the porch. The bed in the master bedroom is incredible!. It is really the perfect location. We look forward to returning next January.

Dec 07, 2021,
Had a wonderful stay! House was clean and great location. Would definitely book again!

Dec 05, 2021,
Wonderful location, great 2-B/2-B unit right in the thick of the KW culture. Loved it, highly recommend Vacation Homes of Key West to get you to the right place, affordably, and with a streamlined process.

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,
5-star’sSent by: Teo ( on 23-Oct-20 9:58 AM Opened Thank you for a 5 Star Review! We are glad that you enjoyed your stay in Key West!

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.

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