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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 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 bedroom with a large bed, a wooden floor, a white wall, and a window with blinds.
A white building with a gabled roof, large windows, and a front porch with chairs.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Duval Street

Popular amenities

  • Balcony
  • Air-conditioning
  • Refrigerator
  • Washing machine
  • Onsite parking available
  • Internet

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪3 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪6 min walk‬
  • Place, South Beach
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 2

1 Queen Bed

Living Room 1

1 Queen Sofa Bed

Master Bedroom

1 Queen Bed

2 bathrooms

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Shower only · Shampoo · Hair dryer

Master Bath

Soap · Towels provided · Bathtub or shower · Toilet · Shower only · Shampoo

Spaces

Porch or lanai
Kitchen
Balcony
Number of living rooms
Garden
Dining area

Add dates for prices

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Living area
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  • Kitchen
  • Washing machine
  • Dryer
9.2 out of 10, Wonderful, (191 reviews)
Charming cottage with private hot tub - one block to Duvall Street

About the area

Key West

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.
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Map
Key West, FL

What's nearby

  • Duval Street - 3 min walk - 0.3 km
  • Ernest Hemingway Home and Museum - 6 min walk - 0.6 km
  • South Beach - 8 min walk - 0.7 km
  • Key West Butterfly and Nature Conservatory - 8 min walk - 0.7 km
  • Southernmost Point - 9 min walk - 0.8 km

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 does it cost to stay at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location?

As of 1 Nov 2026, prices found for a 1-night stay for 2 adults at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location on 5 May 2027 start from AU$775, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, great location, easy processing, great spot
Stayed 5 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Adorable bungalow! Convenient to everything in Old Town. Nice golf club rental directly across the street (Minty’s), lovely spa on the corner (Ocean Wellness) and excellent brunch right down the street (Sarabeth’s) Delightful owners take great care to make your stay easy and comfortable. Highly recommended for anyone who wants the comfort and experience of staying in the heart of Key West
Stayed 6 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
All ya need for a quick getaway in Key West!
Stayed 3 nights in Aug 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, 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
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
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
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
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
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
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
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

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

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
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
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