Cottage in Key West, FL
6 guests · 3 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this cottage rental
Exciting Renovation Update
The Dancing Rooster has just completed a total gut renovation, and we are excited to welcome guests into the newly refreshed home. Updated photos will be coming shortly, and we look forward to sharing the finished results.
The renovation includes a redesigned kitchen with new quartz countertops and appliances, brand-new bathrooms with new tile and marble showers, new flooring throughout, new beds with premium mattresses to help ensure a comfortable night’s sleep, and thoughtfully curated artwork throughout the home that adds warmth and character.
Welcome to The Dancing Rooster
Perfectly situated just two short blocks from Duval Street in the heart of downtown Key West, The Dancing Rooster is a beautifully reimagined 3-bedroom, 2-bath home offering the ideal blend of location, comfort, and island living. Located in the sought-after Simonton Historic Cottage enclave, the home is surrounded by great restaurants, art galleries, boutique shopping, and many of Old Town’s most popular attractions. With so much within easy walking distance, a car is truly unnecessary.
Designed with both style and comfort in mind, the home offers three inviting bedrooms and two baths. Two Queen bedrooms share an en-suite bath that is easily accessible from either room and includes a spacious walk-in marble shower. The third bedroom features a full-size bed, walk-in shower, and private entrance — ideal for added privacy and flexibility. The living room provides a comfortable place to relax, complete with a new L-shaped sofa and sitting countertops for additional casual seating and gathering space.
Each bedroom and the living room are equipped with brand-new HIDEF Samsung 4K Smart TVs. Guests will also enjoy free 300 Mbps AT&T high-speed business internet, cozy linens and towels, and a brand-new central air conditioning system to keep you comfortable in every season.
Ideally located near the marina district and just .7 miles from Fort Zachary Taylor Beach, The Dancing Rooster places you within easy reach of some of Key West’s most beloved destinations. Additional nearby landmarks include the Hemingway House, Duval Street, and the marina district. Street parking is available, though we recommend exploring the island on foot, by bike, or via the Duval Loop.
Directly across the street, you’ll find The Sugar Apple, a health food store offering fresh smoothies, lunch, and healthy options. A CVS is just one block away, and bike and scooter rentals are also nearby.
A 3-night minimum stay is required, and this is a strict no-smoking property. Please contact the owner for any exception to the minimum stay.
Parking Note
There is no dedicated parking included with this rental. Four first-come, first-served spaces are available directly on Simonton Street. We strongly recommend leaving the car parked and using the complimentary Duval Loop bus service, which runs daily and stops just half a block from the cottage.
https://www.cityofkeywest-fl.gov/326/Duval-Loop
Travel Insurance Recommendation
We strongly recommend purchasing travel insurance to protect against illness, medical emergencies, weather-related disruptions, or other unexpected events. For guests traveling during Florida’s hurricane season, June 1 through November 30, travel insurance is especially important. Please note that no refunds will be issued for weather-related disruptions or early departures.
The Dancing Rooster has just completed a total gut renovation, and we are excited to welcome guests into the newly refreshed home. Updated photos will be coming shortly, and we look forward to sharing the finished results.
The renovation includes a redesigned kitchen with new quartz countertops and appliances, brand-new bathrooms with new tile and marble showers, new flooring throughout, new beds with premium mattresses to help ensure a comfortable night’s sleep, and thoughtfully curated artwork throughout the home that adds warmth and character.
Welcome to The Dancing Rooster
Perfectly situated just two short blocks from Duval Street in the heart of downtown Key West, The Dancing Rooster is a beautifully reimagined 3-bedroom, 2-bath home offering the ideal blend of location, comfort, and island living. Located in the sought-after Simonton Historic Cottage enclave, the home is surrounded by great restaurants, art galleries, boutique shopping, and many of Old Town’s most popular attractions. With so much within easy walking distance, a car is truly unnecessary.
Designed with both style and comfort in mind, the home offers three inviting bedrooms and two baths. Two Queen bedrooms share an en-suite bath that is easily accessible from either room and includes a spacious walk-in marble shower. The third bedroom features a full-size bed, walk-in shower, and private entrance — ideal for added privacy and flexibility. The living room provides a comfortable place to relax, complete with a new L-shaped sofa and sitting countertops for additional casual seating and gathering space.
Each bedroom and the living room are equipped with brand-new HIDEF Samsung 4K Smart TVs. Guests will also enjoy free 300 Mbps AT&T high-speed business internet, cozy linens and towels, and a brand-new central air conditioning system to keep you comfortable in every season.
Ideally located near the marina district and just .7 miles from Fort Zachary Taylor Beach, The Dancing Rooster places you within easy reach of some of Key West’s most beloved destinations. Additional nearby landmarks include the Hemingway House, Duval Street, and the marina district. Street parking is available, though we recommend exploring the island on foot, by bike, or via the Duval Loop.
Directly across the street, you’ll find The Sugar Apple, a health food store offering fresh smoothies, lunch, and healthy options. A CVS is just one block away, and bike and scooter rentals are also nearby.
A 3-night minimum stay is required, and this is a strict no-smoking property. Please contact the owner for any exception to the minimum stay.
Parking Note
There is no dedicated parking included with this rental. Four first-come, first-served spaces are available directly on Simonton Street. We strongly recommend leaving the car parked and using the complimentary Duval Loop bus service, which runs daily and stops just half a block from the cottage.
https://www.cityofkeywest-fl.gov/326/Duval-Loop
Travel Insurance Recommendation
We strongly recommend purchasing travel insurance to protect against illness, medical emergencies, weather-related disruptions, or other unexpected events. For guests traveling during Florida’s hurricane season, June 1 through November 30, travel insurance is especially important. Please note that no refunds will be issued for weather-related disruptions or early departures.
Amenities at The Dancing Rooster: Newly Renovated Key West Retreat, One Block to Duval!
Non-smoking
Family friendly
Map of Key West, FL
Ratings and reviews
8 / 10Excellent·Jul 2026
Everything was great with the property, location, cleanliness and communication. The only down fall was no parking.
10 / 10Outstanding·Jun 2026
Great property and host. Nice central location was perfect for a quick 24 hour trip to Kew West. Great value.
8 / 10Excellent·Jun 2026
It was a cute house. Centrally located easy to get to all areas. The parking was pretty good. Only 1 day hard to find a spot out front. Unfortunately the outside of the house was dirty as well as the grounds around the house. The sink in the back bathroom is clogged slow draining. The floor in the whole house is really dirty.
6 / 10Average·Dec 2025
Excellent location. Wrought can walk to just about anywhere you want to on the island. 4 of us stayed in the 3 BR house. 6 people would have been a very tight fit. Bedrooms are small. Tight fit for 2 suitcases. Beds were soft. Pillow's were flat. 2 ice trays in small freezer, so go to CVS down the street to purchase ice. 1bath towel per person for our 6 day stay, which was inadequate in this tropical environment. Both bathrooms ran out of toilet paper. We all really enjoyed being able to sit outside on the front patio. There was room for all 4 of us.
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Top rated by guests
9.8Outstanding
(151 Ratings)
"Great property and host. Nice central location was perfect for a quick 24 hour trip to Kew West. Great value."
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