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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. - 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 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 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 white building with a gabled roof, large windows, and a front porch with chairs. - 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 a garden, laundry facilities and more. Guests can connect to in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms2 bathrooms572 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning
  • Outdoor space

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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.

Property amenities

Internet

  • Available in the cottage: WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • 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
  • Up to 9 kg 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 lift (single-level property)
  • Single level property
  • Stair-free path to entrance
  • Smoke-free property

Services and conveniences

  • Housekeeping on request
  • Iron/ironing board
  • Safe

Location highlights

  • In the city centre
  • 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 organised tours and activities
  • Recycling
  • Some LED lighting used
  • Unit size: 572 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM
Contactless check-out

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

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total (up to 9 kg per pet)

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
On-site parties or group events are strictly prohibited
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
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 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 lighthouse with a white exterior and a black top, surrounded by lush green trees.
    Key West Lighthouse and Keeper's Quarters Museum
    6 min walk - 0.4 miles
  • A beach with people sunbathing, palm trees, and a multi-story building in the background.
    South Beach
    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?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 9 kg per pet.

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

Reviews

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 informationOpens in a new window
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

Cleanliness

9.8

Location

Reviews

Verified

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

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

10/10 Excellent

Jackie M.

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

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

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

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

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

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

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

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

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

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

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

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
Verified

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

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

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

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

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

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

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

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

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