The Dancing Rooster: 2 Blocks from Duval in Old Town.

Top rated by guests
Exterior
Kitchen
Main Entrance off Street - Peaceful and Quiet!
Sitting Area - Back Entrance
Famous Blue Heaven Shower Sign
review stars
10Outstanding
(151 Ratings)
"This was a cozy little bungalow. It was clean and had everything we needed for our stay. Nancy was very responsive and communicated with us in a timely and respectful manner. Location was great. You w..."
Tonya H.
Don't miss out! Price and availability may change
10 / 10
Outstanding(151 Ratings)

Cottage in Key West, FL

6 guests · 3 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this cottage rental

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.

Two of the Queen bedrooms share an en-suite bath easily assessable from either bedroom. It features a very large walk-in shower. The 3rd bedroom features a full sized bed, walk in shower and private entrance. The quaint living room has a new L Shaped Sofa that provides plenty of additional sitting room for kicking back and chill time.

Each bedroom and the living room are equipped with brand new HIDEF Samsung 4K Smart TV’s. In addition, we have recently upgraded the cottage to include FREE 300 Mbps ATT Hi Speed Business Internet, new orthopedic mattresses, and cozy linens – towels to make your stay relaxed and pleasant. There is also a brand new Central Air Conditioning system to help keep you comfortable and snug, especially during the warmer summer months!

Adjacent is a completely equipped kitchen that has granite counter tops, glass cooktop stove, microwave and refrigerator. Even wine and champagne glasses are included! A bicycle lock-up in the courtyard is available.

Blocks from the marina district, and an easy walk (.7 miles) to Ft. Zachary Taylor where Australian Pines tower over the beach. There is on street parking available (Hemmingway House .28 miles, Duval Street 1 block, Marina District 7 blocks, beach .7 miles).

There is a health food store located directly across the street called 'The Sugar Apple' which serves fresh fruit smoothies, lunch, and offers a variety of health food. A CVS is located one block away. A bike and scooter rental location is one block away.

A 3-night minimum stay required and strict No Smoking policy applies. Please contact owner for exception to 3 night minimum

Please note rates are subject to change and are higher during Event Periods such as Fantasy Fest, Gay Pride, Memorial Day, Christmas Week, New Year's Week, Thanksgiving, etc. Longer stays than 3 days may be required during event periods.

NOTE: There is No Dedicated Parking included with this rental. Directly on Simonton Street are (4) spaces and available on first come basis. We do recommend keeping the car parked and walk, bike or use the bus service, The Duval Loop. The Duval Loop provides FREE Hop on, Hop off bus service, operates every day, and stops a half block from the cottage. https://www.cityofkeywest-fl.gov/326/Duval-Loop

IMPORTANT: We strongly recommend purchasing travel insurance to protect against illness, medical emergencies, weather-related issues, or other unexpected circumstances. While travel insurance can be purchased during the booking process, you may want to consider other reputable travel insurance providers, such as Travel Guard (AIG), Nationwide, Allianz, Berkshire Hathaway and Red Sky. We encourage you to review their coverage options and rates to find the best fit for your needs.

For those traveling during Florida's hurricane season (June 1 – November 30), travel insurance is especially important. Please note that NO refunds will be issued for weather-related disruptions or early departures.

Exciting Things Are Coming to The Dancing Rooster!

Beginning August 24, with completion anticipated in early October, The Dancing Rooster will undergo an exciting renovation designed with our guests in mind. We're giving the home a fresh new look, featuring a beautifully redesigned kitchen, new countertops, brand-new bathrooms, new flooring, a new washer and dryer, and stylish, comfortable furnishings throughout.

Our goal has always been to provide a home that is not only exceptionally clean and well-appointed, but also a place where you can truly relax, unwind, and experience the best of Key West. These thoughtful upgrades will create an even more inviting, comfortable, and modern retreat while preserving the charm that makes The Dancing Rooster so special.

We can't wait to share updated photos once the renovation is complete and to welcome you to the newly refreshed Dancing Rooster. We are confident these enhancements will make your next Key West getaway even more comfortable, memorable, and enjoyable. We look forward to hosting you!

Amenities at The Dancing Rooster: 2 Blocks from Duval in Old Town.

Non-smoking
Pets allowed
Family friendly

Map of Key West, FL


Ratings and reviews

10 / 10
Outstanding(151 Ratings)
10 / 10Outstanding·May 2026
This was a cozy little bungalow. It was clean and had everything we needed for our stay. Nancy was very responsive and communicated with us in a timely and respectful manner. Location was great. You will hear roosters every morning.. early.... but that is part of Key West charm. CVS is just a half block away if you need anything. We highly recommend staying at the Dancing Rooster.
8 / 10Excellent·Apr 2026
A great place and experience overall. It might be operator error, but I had trouble finding the codes and instructions for check in - eventually finding them in an old text on the Vrbo site. The property manager said the WiFi password was on the refrigerator and the coffee table - but it wasn’t. We were unable to figure out the tv. I also prefer to have explicit instructions for check out. “Neat and tidy” doesn’t tell me what to do with linens.
10 / 10Outstanding·Apr 2026
Super clean, responsive property manager and great location near Duval Street.
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.

$$$$
expedia logo

FAQs

Is parking included with this cottage?

Parking is not specified as an available amenity at The Dancing Rooster: 2 Blocks from Duval in Old Town.. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.

Is The Dancing Rooster: 2 Blocks from Duval in Old Town. pet friendly?

Yes! This cottage is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at The Dancing Rooster: 2 Blocks from Duval in Old Town.?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.