[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location Cottage with kitchen, a short walk to Duval Street ![Exterior](https://images.trvl-media.com/lodging/115000000/114430000/114429500/114429434/7ff914f2.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Marina](https://images.trvl-media.com/lodging/115000000/114430000/114429500/114429434/898be04c.jpg?impolicy=resizecrop&rw=297&ra=fit) ![2 bedrooms, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/115000000/114430000/114429500/114429434/98dccb6f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining](https://images.trvl-media.com/lodging/115000000/114430000/114429500/114429434/228fc1fa.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior](https://images.trvl-media.com/lodging/115000000/114430000/114429500/114429434/c1f8574c.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location A short walk from Duval Street and Southernmost Point, NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location provides a garden, laundry facilities, and more. Guests can connect to in-room WiFi. 9.8 Exceptional ### Entire home 2 bedrooms2 bathrooms572 sq ft ## Popular amenities - Dryer - Washer - Parking available - Pet-friendly - Kitchen - Outdoor space ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location Welcome to the Jolly Rooster! We’re thrilled to welcome you to our newly renovated, standalone cottage—proudly presented by the owners of the Dancing Rooster. Thoughtfully designed for relaxation and comfort, the Jolly Rooster comfortably hosts up to six guests and blends island charm with modern convenience. Nestled just one block from vibrant Duval Street, you’ll be steps away from Key West’s best dining, shopping, and nightlife—while still enjoying the peace and privacy of your own retreat. Our cottage comes fully equipped with all the essentials for a carefree and memorable stay. Come unwind, explore, and experience the best of island living at the Jolly Rooster! \_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_ The Space This thoughtfully designed retreat includes: • 2 private bedrooms, each with a queen bed + ensuite bath (walk-in showers) • Spacious living area with American Leather queen sleeper (memory foam, no bars/springs) • Smart TVs + high-speed internet throughout • Private entrances for both bedrooms and living room • Sleeps 6 (note: base rate covers 4 guests; $100/night applies for 5th/6th guests using sofa bed) \_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_ Fully Equipped Kitchen Perfect for prepping anything from snacks to full meals, featuring: • Granite countertops • Cooktop stove and Range • Microwave • Refrigerator with ice maker • Coffee maker, toaster, and blender \_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_ Location Highlights • 1 block from Duval Street • Walk to Hemingway House, Marina District, beaches • Across from Sugar Apple natural food café • 1 block to CVS + bike/scooter/golf cart rentals • Duval Loop (free shuttle) stops ½ block away \_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_ Parking & Transportation No dedicated parking. Free street parking on Simonton (first come, first served). Explore by foot, bike, scooter, or golf cart! \_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_ Other Things to Note 3-night minimum stay No smoking We recommend travel insurance—especially during hurricane season (June 1–Nov 30). No refunds for weather or early departures. Travel insurance is strongly recommended, especially during Florida’s hurricane season (June 1 – November 30). No refunds will be issued for weather-related disruptions or early departures. You may consider providers such as Travel Guard (AIG), Nationwide, Allianz, Berkshire Hathaway, or Red Sky. ## Property amenities ### Internet - Available in the cottage: WiFi ### Parking and transportation - Parking on site ### Kitchen - Blender - Coffee/tea maker - Cookware, dishware, and utensils - Ice maker - Microwave - Oven - Paper towels - Refrigerator - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 2 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Bathtub or shower - Hair dryer - Shampoo - Shower - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Living room ### Entertainment - Smart TV ### Outdoor areas - Balcony - Garden ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning ### Pets - Pet friendly - Welcoming dogs only - One pet total (up to 20 lbs per pet) ### Suitability/Accessibility - If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking. - No elevator (single-level property) - Single level property - Stair-free path to entrance - Smoking not allowed ### Services and conveniences - Housekeeping (on request) - Iron/ironing board - Safe ### Location highlights - In the city center - Near a hospital - Near the sea ### Things to do - Ecotours nearby - Fishing nearby - Golfing nearby - Jet skiing nearby - Kayaking nearby - Motor boating nearby - Parasailing nearby - Sailing nearby - Scuba diving nearby - Swimming nearby - Water skiing nearby - Water tubing nearby - Windsurfing nearby ### Safety features - No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - Fire extinguisher - Deadbolt lock ### General - At least 80% lighting from LEDs - Energy-saving switches in guestrooms - Garden - Housekeeping (on request) - Local artist showcase - Locally-owned and organized tours and activities - Recycling - Unit size: 572 square feet ## Similar properties ![Pool](https://images.trvl-media.com/lodging/19000000/19000000/18992300/18992275/3039b647.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Conch Republic Consul General's Cottage.-Historic District Old Town Key West - Pool - Kitchen - Washer - Dryer 9.4 Exceptional 164 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=18992275&PinnedHotelID=18992275&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/64000000/63730000/63723300/63723258/db6f8e09.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Heart of Downtown Key West Cottage With Off-Street Parking Key West Historic District - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 138 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=63723258&PinnedHotelID=63723258&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/68000000/67450000/67446300/67446229/5250914d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Dancing Rooster: 2 Blocks from Duval in Old Town. 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Old Town Key West - Kitchen - Pet-friendly - Free WiFi - Air conditioning 9.4 Exceptional 21 reviews CA $237 CA $667 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29&selected=112579934&PinnedHotelID=112579934&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Contactless check-in available Minimum check-in age: 25 ### Check-out Check-out before 11:00 AM Contactless check-out available ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Pets Pets allowed Service animals are welcome, and are exempt from fees Welcoming dogs only 1 total (up to 20 lbs per pet) ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Onsite parties or group events are strictly prohibited Host has indicated there are no carbon monoxide detectors or gas appliances on the property Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher and a deadbolt lock This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ## About the area Located by the sea, this cottage is in Old Town Key West, a neighborhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and South Beach. Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center are also worth visiting. Jet skiing, kayaking, and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby. [Visit our Key West travel guide](https://www.expedia.ca/Key-West.dx1187) [View more Cottages in Key West](https://www.expedia.ca/Key-West-Cottages.d1187-aaCottages.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C24.55240%2C-81.79848&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=C-3sY2PuWS7zTurkFYkDOBU7h-U=) Key West, FL ### What's nearby - Duval Street - 3 min walk - 0.3 km - Ernest Hemingway Home and Museum - 5 min walk - 0.4 km - South Beach - 8 min walk - 0.7 km - Southernmost Point - 9 min walk - 0.8 km - Mallory Square - 18 min walk - 1.5 km ### Getting around - Key West Intl. Airport (EYW) - 12 min drive ### Restaurants - ‪801 Bourbon Bar - ‬6 min walk - ‪Old Town Tavern - ‬4 min walk - ‪Nine One Five - ‬3 min walk - ‪Better Than Sex - ‬1 min walk - ‪Vinos On Duval - ‬5 min walk ## Frequently asked questions ### Is NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location pet-friendly? > Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 20 lbs per pet. ### How much does it cost to stay at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location? > As of Oct 19, 2025, prices found for a 1-night stay for 2 adults at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location on Nov 4, 2025 start from CA $392.56, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. [Choose your dates](https://www.expedia.ca/Key-West-Hotels-Coming-Soon-July-1-The-Jolly-RoosterNew-2BR2BA-Walk-To-Duval.h114429434.Hotel-Information?rfrr=HOT.HIS.question.link.click) for more accurate prices. ### What time is check-in at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location? > Check-in begins at 4:00 PM. ### What time is check-out at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location? > Check-out is at 11:00 AM. ### Where is NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location located? > Located in Old Town Key West, this cottage is within a 5-minute walk of Tennessee Williams Key West Exhibit and Duval Street. Ernest Hemingway Home and Museum and South Beach are also within 10 minutes. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location Reviews 9.8 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 7 8 - Good 1 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 9.8/10 Cleanliness ### No reviews yet Be the first to leave a review for this property after your stay.