Cottage in Key West, FL
6 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this cottage rental
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
• Any use of the sofa bed—whether your group exceeds 4 guests or not—incurs an additional charge of $100 per night, plus applicable state and local taxes.
________________________________________
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.
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
• Any use of the sofa bed—whether your group exceeds 4 guests or not—incurs an additional charge of $100 per night, plus applicable state and local taxes.
________________________________________
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.
Amenities at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Non-smoking
Pets allowed
Family friendly
Map of Key West, FL
Ratings and reviews
10 / 10Outstanding·May 2026
This unit was exactly as described. We did have trouble finding parking 2 of the 5 days. Very clean, excellent location. Super cute and comfortable unit!
10 / 10Outstanding·May 2026
We loved the Jolly Rooster! The cottage is so cute & super clean. That's always a big plus for us. You can tell it's very well taken care of. It was so nice to have 2 bathrooms & a washer & dryer. Beds were very comfortable, and so was the sofa bed. Living area is small, but we were exploring Key West most of the time or sitting on the front patio area of the cottage. There are also chairs on the front porch and there is a back patio area as well. Loved all the beautiful flowers & trees surrounding the front patio area. There is only street parking, but we were lucky enough to get a spot right in front of the cottage. Had to park a couple streets over one of the days, but not a far walk. The neighborhood is nice & we were able to walk just about everywhere. Duval St. is just around the corner. The cottage is perfect for 2-4 people. We highly recommend checking it out.
10 / 10Outstanding·May 2026
Jolly Rooster cottage was a prefect and great location. Cottage was very clean. We had a great girls trip!We will definitely be back.
10 / 10Outstanding·Apr 2026
The jolly rooster was a fantastic VRBO! The location couldn’t be better, it was right off of Duval so it was convenient to all the action yet quiet. Well stocked, and super friendly and easy to get a hold of host! Only note is that parking is difficult to find, and one of the bedrooms is a walk-through. But hands-down will go back here anytime! Thanks for a great stay
$$$$
Top rated by guests
10Outstanding
(34 Ratings)
"This unit was exactly as described. We did have trouble finding parking 2 of the 5 days. Very clean, excellent location. Super cute and comfortable unit!"
Jennifer K.Don't miss out! Price and availability may change
