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

Cottage with kitchen, 3-minute walk to Duval Street

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

Exterior - NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location (Key West)
Dining - NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location (Key West)
2 bedrooms, in-room safe, iron/ironing board, WiFi - NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location (Key West)
Exterior - NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location (Key West)
Marina - NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location (Key West)
Close to Ernest Hemingway Home and Museum and Duval Street, 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

9.6 out of 10
Exceptional

Entire home

2 bedrooms2 bathrooms53 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning
  • Outdoor space
The current price is NZ$1,297
includes taxes & fees
9 Jan - 10 Jan 2026

Add dates for prices

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!
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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
• Sleeps 6 (note: base rate covers 4 guests; $100/night applies for 5th/6th guests using sofa bed)
________________________________________
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!
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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

  • At least 80% lighting from LEDs
  • Energy-saving switches in guestrooms
  • Garden
  • Housekeeping (on request)
  • Local artist showcase
  • Locally-owned and organised tours and activities
  • Recycling
  • Unit size: 572 square feet

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includes taxes & fees
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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

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

Map
Key West, FL

What's nearby

  • Duval Street - 3 min walk - 0.3 km
  • Ernest Hemingway Home and Museum - 5 min walk - 0.4 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

  • ‪801 Bourbon Bar - ‬6 min walk
  • ‪Old Town Tavern - ‬4 min walk
  • ‪Nine One Five - ‬3 min walk
  • ‪Ocean Grill & Bar - ‬3 min walk
  • ‪Viva Argentinian Steakhouse - ‬4 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 does it cost to stay at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location?

As of 22 Dec 2025, prices found for a 1-night stay for 2 adults at NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location on 9 Jan 2026 start from NZ$1,297.10, 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. Ernest Hemingway Home and Museum and Florida Keys Beaches 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. 8 out of 10 reviews
Rating 8 - Good. 2 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

9.8

Cleanliness

9.6

Location

Reviews

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

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

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

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

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

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