NEW! - The Jolly Rooster CottagenSteps to Duval - Prime and Quiet Location | Cottage in Key West, FL
2 Bedroom Cottage with Oceanfront, Internet and Ocean View
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!
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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)
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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
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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
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Parking & Transportation
No dedicated parking. Free street parking on Simonton (first come, first served).
Explore by foot, bike, scooter, or golf cart!
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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.
NEW! - The Jolly Rooster CottagenSteps to Duval - Prime and Quiet Location is located in Key West Historic District. NEW! - The Jolly Rooster CottagenSteps to Duval - Prime and Quiet Location provides accommodation, featuring Security/Safety, Oceanfront, Internet, among other amenities. This Cottage features Security/Safety, Oceanfront, Internet, to make your stay a comfortable one.
NEW! - The Jolly Rooster CottagenSteps to Duval - Prime and Quiet Location has 2 Bedrooms , 2 Bathrooms, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cottage because of the excellent services rendered by the owner or manager of this Cottage, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cottage has a friendly neighborhood, and the Key West Historic District has interesting places to visit. If you want to learn more about the Cottage in Key West Historic District, such as places to visit and things to do nearby, you can check below to learn more.
Amenities
Facility Overview
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Air conditioning
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Soap
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Bathtub or shower
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Shampoo
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2 bathrooms
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Toilet paper
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Towels provided
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Hair dryer
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Bed sheets provided
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2 bedrooms
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Dining table
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Living room
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Stovetop
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Ice maker
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Refrigerator
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Microwave
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Cookware/dishes/utensils
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Oven
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Coffee/tea maker
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Toaster
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Blender
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Laundry facilities
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Washing machine and dryer
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Near laundromat
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Onsite parking
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Welcoming dogs only
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1 total (up to 20 lbs per pet)
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Pet friendly
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No elevator (single level property)
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If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
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Smoke-free property
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Stair-free path to entrance
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Jet skiing nearby
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Parasailing nearby
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Windsurfing nearby
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Water skiing nearby
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Golf nearby
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Fitness facilities nearby
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Power boating nearby
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Fishing nearby
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Ecotours nearby
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Sailing nearby
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Smart TV
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Energy-saving switches
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Recycling
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Locally-owned & organized tours & activities
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At least 80% lighting from LEDs
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Local artist showcase
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Unit size: 572 sq ft (53 sq m)
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Spanish
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English
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In the city center
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Near the sea
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Near a hospital
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Iron/ironing board
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Safe
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Limited housekeeping
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WiFi available
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Garden
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Balcony
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Smoke detector installed (host has indicated there is a smoke detector on the property)
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Fire extinguisher
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Deadbolt lock
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No carbon monoxide detector (host has indicated there is no carbon monoxide detector or gas appliances on the property)
Policies
FAQ's
Is this Key West Historic District cottage pet-friendly for guests?
Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.
Does the Key West Historic District cottage have a swimming pool?
No, this Key West Historic District cottage does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in Key West Historic District cottage?
Best-rates for the Key West Historic District cottage starts from $461 per night with includes Oceanfront, Internet, Ocean View, Balcony/Terrace, Bedding/Linens, Wellness Facilities, Child Friendly, Laundry, Air Conditioner, Parking, Pet Friendly, TV, Kitchen, View, Security/Safety with all other facilities. Casai.nz matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.
Is Key West Historic District cottage a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this cottage Good or guests have recommended them suitable for families. As reported by the owner or manager, the cottage has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the Key West Historic District cottage wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Key West Historic District cottage has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the Key West Historic District cottage?
Based on the information reported by the owner or manager, the Key West Historic District cottage indicates 1 day stay policy at this cottage. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for Key West Historic District cottage?
Based on the information reported by the owner or manager, details for the cancellation policy for the Key West Historic District cottage are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
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