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

Cottage near Duval Street in Key West

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Exterior
Marina
2 bedrooms, in-room safe, iron/ironing board, WiFi
Exterior
Dining

Reviews

9.8 out of 10
Exceptional

Entire home

2 bedrooms2 bathrooms53 sq m

Popular amenities

  • Parking available
  • Dryer
  • Pet-friendly
  • Washer
  • Kitchen
  • Outdoor space

Explore the area

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

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About the area

Key West

Seaside stay .Within a 10-minute walk of this Old Town Key West cottage, you'll find Duval Street and Ernest Hemingway Home and Museum. Also, Southernmost Point is within half a mile (1 km) and Mallory Square is within 2 miles (3 km).
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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
  • Southernmost Point - 9 min walk - 0.8 km
  • Mallory Square - 18 min walk - 1.5 km

Getting around

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

Restaurants

  • ‪801 Bourbon Bar - ‬6 min walk
  • ‪Old Town Tavern - ‬4 min walk
  • ‪Nine One Five - ‬3 min walk
  • ‪Better Than Sex - ‬1 min walk
  • ‪Vinos On Duval - ‬5 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
• 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!
________________________________________
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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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

  • At least 80% lighting from LEDs
  • Energy-saving switches in guestrooms
  • Garden
  • Housekeeping (on request)
  • Local artist showcase
  • Locally-owned and organized tours and activities
  • Recycling
  • 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

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 (weight limit: 20 lbs per pet)
  • Service animals are exempt from fees

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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.