Entire home

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

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

A wooden pathway leading to a beach with palm trees and a clear sky. - The Dancing Rooster: 2 Blocks from Duval in Old Town. (Key West)
A white building with a gabled roof, large windows, and a front porch with chairs. - The Dancing Rooster: 2 Blocks from Duval in Old Town. (Key West)
A rustic wooden gate with a sign reading "Blue Heaven" and another sign advertising showers for $1.00 to watch for $2.00. - The Dancing Rooster: 2 Blocks from Duval in Old Town. (Key West)
A two-story building with balconies, surrounded by lush greenery and palm trees. - The Dancing Rooster: 2 Blocks from Duval in Old Town. (Key West)
A bedroom with a bed, a nightstand, a lamp, a ceiling fan, a door, and a wall-mounted anchor decoration. - The Dancing Rooster: 2 Blocks from Duval in Old Town. (Key West)
A short walk from Duval Street and Southernmost Point, The Dancing Rooster: 2 Blocks from Duval in Old Town. provides laundry facilities and more. Stay connected with free in-room WiFi.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 6750 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Add dates for prices

About this property

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

  • 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!

Property amenities

Beach

  • Beach nearby

Internet

  • Available in the cottage: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Electric kettle
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • Service animals only (pets not allowed)

Suitability/Accessibility

  • No elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina
  • Near the sea

Things to do

  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 750 square feet

Similar properties

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
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed (service animals welcome)

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 is a carbon monoxide detector 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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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

We should mention

This property does not have elevators

About the area

Located near the beach, this cottage is in Old Town Key West, a neighborhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Key West Butterfly and Nature Conservatory and The Kite House are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and ecotours. Visit our Key West travel guide
View more Cottages in Key West
Map
Key West, FL

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    3 min walk - 0.3 km
  • A vintage typewriter on a wooden table with a notebook and pen beside it.
    Ernest Hemingway Home and Museum
    6 min walk - 0.6 km
  • A beachside resort with palm trees, a large white building, and a checkered pattern on the sand.
    South Beach
    8 min walk - 0.7 km
  • A butterfly on a plant with green leaves and yellow flowers.
    Key West Butterfly and Nature Conservatory
    8 min walk - 0.7 km
  • A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
    Southernmost Point
    9 min walk - 0.8 km

Getting around

  • Key West Intl. Airport (EYW)
    9 min drive

Restaurants

  • Circle K
    4 min walk
  • Moondog Cafe & Bakery
    6 min walk
  • 801 Bourbon Bar
    6 min walk
  • Old Town Tavern
    4 min walk
  • Bourbon Street Pub
    7 min walk

Frequently asked questions

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

No, only service animals are welcome at the property.

How much does it cost to stay at The Dancing Rooster: 2 Blocks from Duval in Old Town.?

As of Sept 24, 2026, prices found for a 1-night stay for 2 adults at The Dancing Rooster: 2 Blocks from Duval in Old Town. on Oct 20, 2026 start from CA $703, excluding 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?

Onsite parking is available at the property.

What time is check-in at The Dancing Rooster: 2 Blocks from Duval in Old Town.?

Check-in begins at 4:00 PM.

What time is check-out at The Dancing Rooster: 2 Blocks from Duval in Old Town.?

Check-out is at 11:00 AM.

Where is The Dancing Rooster: 2 Blocks from Duval in Old Town. located?

Located in Old Town Key West, this cottage is within a 5-minute walk of Tennessee Williams Key West Exhibit and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 10 minutes.

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The Dancing Rooster: 2 Blocks from Duval in Old Town. 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. 134 out of 151 reviews
Rating 8 - Good. 16 out of 151 reviews
Rating 6 - Okay. 1 out of 151 reviews
Rating 4 - Poor. 0 out of 151 reviews
Rating 2 - Terrible. 0 out of 151 reviews

9.8

Cleanliness

10

Location

10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Super clean, responsive property manager and great location near Duval Street.
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. Just as advertised.They went out of there way to allow us to check in early and the property manager was great. Would definitely stay here again.
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location is perfect. Easy walk to Duval and other places. Quiet, quaint neighborhood.
Stayed 5 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place, great location! Worked out perfect!
Stayed 4 nights in Jan 2026
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful bungalow. Clean and has everything you need. Comfortable and located walkable distance to all attractions on the island. Nice neighborhood! Enjoyed our stay and plan to return!
Stayed 3 nights in Dec 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location is the strongest selling point for sure. The unit is small but makes the most of its space.
Stayed 7 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Responsive host & property manager. Great location within walking distance to shops, restaurants, & attractions. Property was clean & beds comfortable, but would recommend having spare blankets should anyone want to sleep on the sofa. Would definitely stay there agsin.
Stayed 4 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place and location

Great place and convenient location to get everywhere you need in Key West
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfortable; great location

The home looks just like the pictures and was very comfortable. It was a very quick walk to Duval Street which we loved. We would stay here again!
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Enjoyed our stay!

Couldn't have asked for anything better on our weekend getaway to the Keys. The location was spot on -- a short walk to everything!
Stayed 3 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Place

We had a great stay and wonderful trip to Key West. The location is great for walking and Nancy the property manager was great and very helpful in anything we asked.
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice place, good communication

3 relaxing days
Stayed 3 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a perfect location in Olde Town Key West! We walked to many nice places and, if it was a bit further, a very reasonable taxi took us there. Our favorite part was sitting on the front porch and just watching the town people go by! The awning was the icing on the cake as it created the perfect shade to sit and enjoy! Inside was ample room, nice kitchen and BIG TV’s! We will certainly book here again for our next Keys trip.
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Long weekend.

Clean, perfect location in Old Town Key West. The property manager was so accommodating and quickly got back to me with answers to my questions. Would definitely stay there again.
Stayed 3 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West birthday celebration

The house was perfect for our group of 3 couples- we loved sitting out on the front porch - got lucky and parked golf cart in front every evening- close to Duval St - quiet area
Stayed 4 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Dancing at the Roost

The Dancing Rooster has a fantastic location. We walked everywhere! It was very clean and had everything we needed for a little cooking. We very much enjoyed our stay.
Stayed 4 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was exactly as described. It was clean, comfortable, and spacious for our party of 4. Communication was friendly and expedient. Check in was simple. Location, location, location! We were within walking distance to so much and rented a golf cart for anything further away. I would definitely book again! Thank you…10/10!
Stayed 4 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute Bungalow

Great stay at Bungalow 5! The place was clean and well equipped and you can’t beat the location. Good communications and accurate in every way.
Stayed 4 nights in Feb 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Right Space Right Location!

Our 3 bedroom, 2 bathroom bungalow accommodated the 5 of us perfectly. Kitchen had all that we needed, space to sit outside, and so close to the action on Duval St.
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very nice stay !

This location is great - easy to get to bight and Duval St. The interior was very clean. Good shower, good room lay out, good mattress. Like the two different entrances as I stayed with my sister's family which gave us privacy. Good prompt response from owner and staff.
Stayed 4 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key west one night

Very nice and comfortable
Stayed 1 night in Jan 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Location

This place was in a perfect location. It was a easy walk to Duval and to many of the bars and restaurants. The operating manager responded quickly to a couple of minor issues that we had. I would definitely stay there again.
Stayed 4 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Overdue visit to Key West

Fantastic week, bungalow was the perfect location to enjoy everything Key West has to offer. Spent late evenings on the patio playing games and speaking with passerby’s.
Stayed 6 nights in Feb 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great home and location!

The location of this property is unbeatable! Very close to Duval street with plenty of restaurants and shopping nearby. The home was clean and well kept up also. Property manager was very quick to respond and helpful!
Stayed 3 nights in Aug 2024