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

Key West, Florida
$444 avg/night Minimum Stay 1 Nights
Bed 2

Bed

Bath 2

Bath

Home Cottage

Property Type

Sleep 6

Max Sleeps

Night 1 nights

Min Stay

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
• 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.
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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
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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
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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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    1 Total (up To 20 Lbs Per Pet) Pet Friendly Welcoming Dogs Only
  • DINING

    Dining Table
  • SAFETY

    Deadbolt Lock Fire Extinguisher No Carbon Monoxide Detector (host Has Indicated There Is No Carbon Monoxide Detector Or Gas Appliances On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Energy-saving Switches Local Artist Showcase Locally-owned & Organized Tours & Activities Recycling Unit Size: 572 Sq Ft (53 Sq M) Uses Some LED Lighting
  • KITCHEN

    Blender Coffee/tea Maker Ice Maker Microwave Oven Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Garden
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English Spanish
  • THINGS TO DO

    Ecotours Nearby Fishing Nearby Fitness Facilities Nearby Golf Nearby Jet Skiing Nearby Parasailing Nearby Power Boating Nearby Sailing Nearby Scuba Diving Nearby Water Skiing Nearby
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    In The City Center Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Limited Housekeeping Safe
  • 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) Smoke-free Property Stair-free Path To Entrance

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Jackie M.

    Submitted Feb 8, 2026

    Stayed Feb 4, 2026

    Great location, freshly renovated

  • Mike M.

    Submitted Jan 27, 2026

    Stayed Jan 23, 2026

    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!

  • Joseph A.

    Submitted Jan 20, 2026

    Stayed Jan 15, 2026

    Excellent location, quiet neighborhood, beautiful modern remodel, excellent new furnishing and amenities.

  • Rebeca T.

    Submitted Dec 30, 2025

    Stayed Dec 24, 2025

    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.

  • Patricia W.

    Submitted Nov 19, 2025

    Stayed Nov 1, 2025

    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.

  • rebecca r.

    Submitted Nov 18, 2025

    Stayed Nov 12, 2025

    Great location and host was awesome!

  • J W.

    Submitted Oct 15, 2025

    Stayed Oct 8, 2025

    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.

  • Christie C.

    Submitted Sep 29, 2025

    Stayed Sep 21, 2025

    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.

  • Karen V.

    Submitted Sep 20, 2025

    Stayed Sep 14, 2025

    I nice place cool place to go back to after touring Key West.

  • Cortne R.

    Submitted Sep 15, 2025

    Stayed Sep 3, 2025

    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!!

  • Bill K.

    Submitted Sep 14, 2025

    Stayed Sep 11, 2025

    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.

  • Cassidy D.

    Submitted Aug 18, 2025

    Stayed Aug 15, 2025

    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!

  • Michael M.

    Submitted Aug 13, 2025

    Stayed Aug 5, 2025

    This was the perfect cottage for our stay. Very clean, nicely remodeled, great location to everything. It had everything we needed for or stay.

  • Esther G.

    Submitted Jul 31, 2025

    Stayed Jul 26, 2025

    Easy walk to everything! Comfortable stay.

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Total

Includes taxes and fees
$444+
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