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

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A two-story building with balconies, surrounded by lush greenery and palm trees.
A bedroom with a large bed, a wooden floor, a white wall, and a window with blinds.
A modern living room with a blue sofa, a dining table with wicker chairs, a chandelier, and artwork on the walls.
A dining area with a round table, wicker chairs, a floral rug, and a chandelier.
A white building with a gabled roof, large windows, and a front porch with chairs.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms2 bathrooms572 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪3 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪6 min walk‬
  • Place, Southernmost Point
    ‪9 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

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About the neighborhood

Key West

Located in Old Town Key West, this cottage is within a 5-minute walk of Duval Street and within 15 minutes of other popular attractions like Florida Keys Beaches. The cottage includes a kitchen, a balcony, and a refrigerator.
View more Cottages in Key WestOpens in a new window

What's nearby

  • Duval Street - 3 min walk - 0.2 miles
  • Ernest Hemingway Home and Museum - 6 min walk - 0.4 miles
  • Key West Lighthouse and Keeper's Quarters Museum - 6 min walk - 0.4 miles
  • South Beach - 8 min walk - 0.5 miles
  • Southernmost Point - 9 min walk - 0.5 miles

Getting around

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

Restaurants

  • ‪Moondog Cafe & Bakery - ‬6 min walk
  • ‪Circle K - ‬4 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬6 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪801 Bourbon Bar - ‬6 min walk

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
• 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.
The cottage is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 2 bedrooms. Other standard amenities include a washing machine, a coffee maker, and a safe. Limited housekeeping is available.

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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

  • Garden
  • Housekeeping (on request)
  • Local artist showcase
  • Locally-owned and organized tours and activities
  • Recycling
  • Some LED lighting used
  • Unit size: 572 square feet

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
Information provided by the property may be translated using automated translation tools

Pets

  • This property welcomes pets
  • Dogs only
  • 1 total (20 lbs is the maximum weight per pet)
  • Service animals exempt from fees

Children and extra beds

Children allowed: ages 0-17

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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher, a smoke detector, and a deadbolt lock.

Frequently asked questions

What's there to do within easy reach of this cottage?

This cottage is situated in Old Town Key West, just steps from Duval Street and Ernest Hemingway Home and Museum, and within a short walk of Florida Keys Beaches. You'll also find Southernmost Point and Fort Zachary Taylor Historic State Park less than a mile away.

Is there parking available at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location?

No, this cottage doesn't offer parking.

Is this cottage associated with a casino?

No, this cottage is not connected to a casino.

Is there an indoor pool at this cottage?

No, there is no indoor pool at this cottage.

Is NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location a good place to stay for couples?

Couples staying at this cottage will appreciate amenities like a kitchen and a smart TV as well as a garden.

Are there hot tubs at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location?

No, there isn't a spa tub at this cottage.

Does this cottage offer breakfast?

No, this cottage doesn't offer breakfast.

Does this cottage allow pets to stay free of charge?

Although dogs can't stay for free, they are welcome at this cottage.

Are there connecting rooms at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location?

No, this cottage doesn't feature connecting guestrooms.

What is the closest airport to this cottage?

The closest major airport to this cottage is Key West Intl. Airport (EYW), which is 3.6 mi away (12 minutes by car).

Are there rooms with balconies at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location?

Yes, every cottage at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location comes with a balcony.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 31 out of 33 reviews
Rating 8 - Good. 2 out of 33 reviews
Rating 6 - Okay. 0 out of 33 reviews
Rating 4 - Poor. 0 out of 33 reviews
Rating 2 - Terrible. 0 out of 33 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Phyllis B.

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

Jessica C.

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

Juleigh N.

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

Norm & Debbie O.

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

rebecca r.

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

Jackie M.

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

10/10 Excellent

Becky D.

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

Joseph A.

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

Marty B.

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

lindsey k.

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

Karen V.

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

Michael M.

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

Christie C.

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

Esther G.

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

Mike M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property looks recently renovated, communications were excellent.Street parking is all there is- good news wait until 5ish day one and there should be spots right in front for free.Had a great time!
Stayed 4 nights in Jan 2026
Verified review

10/10 Excellent

Cassidy D.

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
Verified review

10/10 Excellent

Charlene K.

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

Kanureet S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family of 3 loved the stay. It was not in busiest part of town but walkable to all main attractions. House was clean and had a modern reno recently it seems. We didn’t use kitchen so can’t comment on that. Washer dryer are in good condition and came handy after beach days. We kept our water shoes out on the porch so as not to bring sand inside. Fort Zachary beach was the best and for breakfast we loved Moondog cafe and La grignote. Sugar apple smoothies were great as well.
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

Cortne R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved EVERYTHING about this cute cottage. The location is FANTASTIC! QUIET LOCATION! but still close enough To the fun! Rent some scooters and scoot along the island! Parking on street was right out front and super convenient! Will stay here again!!
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

Bill K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a great little 2 bedroom with a pullout couch, appointed kitchen I used to cook breakfast each day. Right at the intersection of US 1 and Simonton. Nancy, the property manager was great to work with and easy to communicate with. I will stay here again next year.
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

jennifer p.

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

10/10 Excellent

Patricia R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Apr 2026
Verified review

8/10 Good

J W.

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

Rebeca T.

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

Patricia W.

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

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