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NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

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A kitchen with white cabinets, a microwave, stove, and a dining table with chairs. - NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location (Key West)
A two-story building with balconies, surrounded by lush greenery and palm trees. - NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location (Key West)
A modern living room with a blue sofa, a dining table with wicker chairs, a chandelier, and artwork on the walls. - NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location (Key West)
A dining area with a round table, wicker chairs, a floral rug, and a chandelier. - NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location (Key West)
A bedroom with a large bed, a wooden floor, a white wall, and a window with blinds. - NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location (Key West)
A short walk from Duval Street and Southernmost Point, NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location provides golfing on-site, a garden and laundry facilities. Guests can connect to in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Parking available

Add dates for prices

About this property

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
    • 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.

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About the area

Located by the sea, this cottage is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. 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
View more Cottages in Key West
Map
Key West, FL

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    3 min walk - 0.2 miles
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    6 min walk - 0.4 miles
  • A wooden sign with information about South Beach, Key West, Florida, including public beach status, restaurant hours, and beach chair rental.
    South Beach
    8 min walk - 0.5 miles
  • A building with a sign reading "The Key West Butterfly & Nature Conservatory".
    Key West Butterfly and Nature Conservatory
    8 min walk - 0.5 miles
  • A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
    Southernmost Point
    9 min walk - 0.5 miles

Getting around

  • Key West, FL (EYW-Key West Intl.)
    12 min drive

Restaurants

  • Circle K
    4 min walk
  • Moondog Cafe & Bakery
    6 min walk
  • 801 Bourbon Bar
    6 min walk
  • Old Town Tavern
    4 min walk
  • Bourbon Street Pub
    7 min walk

Frequently asked questions

Is NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location pet-friendly?

No, only service animals are welcome at the property.

How much is parking at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location?

On-site parking is available at the property.

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?

Checkout 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. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 10 minutes.

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Reviews

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location Reviews

10

Exceptional

10

Cleanliness

9.8

Location
Rating 10 - Excellent. 34 out of 36 reviews
Rating 8 - Good. 2 out of 36 reviews
Rating 6 - Okay. 0 out of 36 reviews
Rating 4 - Poor. 0 out of 36 reviews
Rating 2 - Terrible. 0 out of 36 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, location
The location of jolly rooster was great, and we managed to get parking right outside. Very clean property. Host was very responsive to emails while we were there. Would definitely book again
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and host was awesome!
Stayed 5 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, super clean. Great host communication. Thanks for a terrific stay!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, freshly renovated
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time at the Jolly Rooster, it was modern, clean, and very comfortable. Easy walk to any of the places in town that you want to get to. Would definitely stay there again! Thanks so much
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location, quiet neighborhood, beautiful modern remodel, excellent new furnishing and amenities.
Stayed 4 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I nice place cool place to go back to after touring Key West.
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Loved the location. It was very clean and loved the decor. Very comfortable. Everything we needed. Loved the cleaning ladies that were there when we picked up our luggage.
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 5 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had the best trip. Beds were super comfortable. The location of property made exploring the island so convenient. The best excursion we did was the dolphin/sandbar boat tour.
Stayed 6 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location, location!

Easy walk to everything! Comfortable stay.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house clean and the property was up kept and beautiful. We were only 2 people in the house, it may be nice to know if there were 4 of us that you walk through one bedroom to get to the next or go outside of the house and back in the main entry. The location is awesome and house is beautiful. When we messaged the manager, she was always very prompt to address anything. Thank you for a great stay!
Stayed 17 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing location - close to every where you want to be but removed from any chaos. Extremely walkable location. Excellent communication from owner and property manager and very accommodating. Fit our needs for a group of 5 women on 40th birthday celebration trip. We did not use the kitchen for cooking but did see basic cooking supplies. You do need to walk through one bedroom to get to another and to walk through the bedroom to get to the bathroom, but we knew this from the listing and it was not an issue for us at all. We enjoyed the table in the front courtyard and the porch in the mornings. Would absolutely stay here again and would rent another property listed by this owner.
Stayed 3 nights in Mar 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
The place was adorable. So cute and perfect for what we needed while on our stay in key west. The place is newly remodeled. Beds were comfy. Not a lot of space as this is only 500 sq feet but 4 of us stayed comfortably. The only complaint I would have is there is no set parking. You have to fight for one of the 5 spaces out front and they are very hard to come by as they are not permitted for the rentals.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The unit was neat, clean, and well maintained, and the location was perfect for our stay. Everything was as described and made for a comfortable visit.One thing to note for larger groups: if you have more than four people, those sleeping in the living room will need to walk through the middle bedroom to access the bathroom. Additionally, access to the second bedroom is either through the middle bedroom or directly from outside the house, which may not be ideal for everyone.The listing mentions one parking space, but it is not designated. If the spot in front of the house is taken, you may need to find parking elsewhere, potentially on a different street. Overall, it’s a great place to stay, especially for smaller groups who don’t mind the layout.
Stayed 3 nights in Dec 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place. Good location. There should be a book or at least a lamenated 8X10 paper with instructions. We didn't see the tiny note that was pasted on the wall near the sink for a few days. The note instructed us to put the sheets or towels in the wash but there wasn't any laundry detergent. We had to buy sponges to wash the dishes because there weren't any and there was no dishwasher. No sheets for couch and had to call to ask for them. Air conditioner wasn't working when we arrived. They sent someone to fix and he came quickly.
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property is in a perfect location and had everything we needed. The furnishings are quality and also perfect. The property manager was super helpful and responsive. I would choose this property again.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful property! We enjoyed our stay! Property hosts were very attentive to every question we had. Highly recommend!
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Jolly Rooster cottage was a prefect and great location. Cottage was very clean. We had a great girls trip!We will definitely be back.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just a wonderful place to stay. Beds are great and the place is ultra clean... the location is the best for Duval Street walking. First time here.We will book here again, such a cute place. Chickens are a great addition!!
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay in Key West! Clean, well-located, and exactly as advertised. Easy check-in and responsive host. Would definitely book again.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Jolly Rooster's location was extremely convenient to everything we wanted to walk to in Key West! We walked a lot, which made the downside of sometimes hard-to-come-by street parking less of an issue.
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was the perfect cottage for our stay. Very clean, nicely remodeled, great location to everything. It had everything we needed for or stay.
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome place to stay. Very clean and property manager responds super quickly. In a beautiful location super close to the main area. Bathrooms are a little tight but the decor is beautiful!
Stayed 3 nights in Aug 2025