Entire home

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

Choose dates to view prices

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.
A bedroom with a bed, a nightstand, a lamp, a ceiling fan, a door, and a wall-mounted anchor decoration.
A two-story building with balconies, surrounded by lush greenery and palm trees.
A rustic wooden gate with a sign reading "Blue Heaven" and another sign advertising showers for $1.00 to watch for $2.00.
A white building with a gabled roof, large windows, and a front porch with chairs.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 6750 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Explore the area

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

Room options

You may also like

About the neighborhood

Key West

Located in Old Town Key West, this cottage is within a 5-minute walk of Duval Street and within 15 minutes of other popular attractions like Florida Keys Beaches. The cottage includes a kitchen, a patio, and a fenced private yard.

What's nearby

  • Duval Street - 3 min walk - 0.2 miles
  • Ernest Hemingway Home and Museum - 6 min walk - 0.4 miles
  • Key West Lighthouse and Keeper's Quarters Museum - 6 min walk - 0.4 miles
  • South Beach - 8 min walk - 0.5 miles
  • Southernmost Point - 9 min walk - 0.5 miles

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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!
The cottage is air-conditioned and features a kitchen, 2 bathrooms, and a patio, and there's space to spread out with 3 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a fenced private yard, and a coffee maker.

Similar properties

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

  • Pet friendly
  • Welcoming dogs only
  • One pet total (up to 20 lbs per pet)

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

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available

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

  • This property welcomes pets
  • Dogs only
  • 1 total (20 lbs is the maximum weight per pet)
  • Restrictions apply
  • For more information, guests can reach out to the property at the number on the booking confirmation
  • Service animals exempt from fees
  • Note from host: must be under 20 pounds

Children and extra beds

Children allowed: ages 0-17

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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock.

Additional information about polices, regulations, and more:

  • There are no elevators.

Property is also known as

Vrbo Property
Southernmost Retreat 2 Blocks From Duval in Old Town
Southernmost Retreat 2 Blocks from Duval in Old Town.
Southernmost Retreat: 2 Blocks from Duval in Old Town. Cottage
Southernmost Retreat: 2 Blocks from Duval in Old Town. Key West

Frequently asked questions

What's there to see close to this cottage?

This cottage is situated in Old Town Key West, just steps from Duval Street and Ernest Hemingway Home and Museum, and within a short walk of Florida Keys Beaches. You'll also find South Beach and Southernmost Point less than a mile away.

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

As of Jul 29, 2026, prices found for a 1-night stay for 2 adults at The Dancing Rooster: 2 Blocks from Duval in Old Town. on Aug 23, 2026 start from $619, including 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.

Will I be able to park at The Dancing Rooster: 2 Blocks from Duval in Old Town.?

No, there isn't parking available at the cottage.

Is this cottage next to a casino?

No, this cottage is not connected to a casino.

Is there an indoor pool at this cottage?

No, there is no indoor pool at this cottage.

What will couples enjoy most about a stay at The Dancing Rooster: 2 Blocks from Duval in Old Town.?

Couples will appreciate amenities at this cottage, including a kitchen and a smart TV in each cottage and a kitchen in some.

Are there hot tubs at The Dancing Rooster: 2 Blocks from Duval in Old Town.?

No, there isn't a spa tub at this cottage.

Does this cottage provide breakfast?

No, this cottage doesn't offer breakfast.

Does this cottage allow pets to stay free of charge?

Although dogs can't stay for free, they are welcome at this cottage.

Are there connecting rooms at The Dancing Rooster: 2 Blocks from Duval in Old Town.?

No, there aren't connecting guestrooms at this cottage.

Where is the closest airport to this cottage?

The closest major airport to this cottage is Key West Intl. Airport (EYW), which is 3.5 mi away (9 minutes by car).

Can I book a room with a balcony at The Dancing Rooster: 2 Blocks from Duval in Old Town.?

Yes, every cottage at The Dancing Rooster: 2 Blocks from Duval in Old Town. comes with a patio.

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 133 out of 150 reviews
Rating 8 - Good. 16 out of 150 reviews
Rating 6 - Okay. 1 out of 150 reviews
Rating 4 - Poor. 0 out of 150 reviews
Rating 2 - Terrible. 0 out of 150 reviews

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Mercedes A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a great stay. A nice walk to duval for nightlife!
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

E A M.

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

10/10 Excellent

JEFFREY Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Rhonda B.

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

10/10 Excellent

Katharine L.

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

10/10 Excellent

michael k.

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

10/10 Excellent

Sherry H.

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

8/10 Good

Mike B.

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

10/10 Excellent

Jason S.

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

10/10 Excellent

Matthew C.

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

Excellent family trip!

Great time. Would stay again.
Stayed 5 nights in Jun 2025
Verified

10/10 Excellent

Bob C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home , that was perfect for our family of 5! Loved the double door accessibility. Very accommodating!
Stayed 4 nights in Nov 2025
Verified

8/10 Good

Angela F.

Liked: Cleanliness, check-in, communication, location
Great location cleaning service was super nice was able to leave luggage at house before check in time plane arrived early so we didnt have to carry luggage around answer to question was prompt only thing waa shower heaad in one bathroom would not stay up and shows they have a grill on site but that has not yet been replaced everything else was great
Stayed 6 nights in Feb 2026
Verified

10/10 Excellent

Leslie M.

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

Great place

We enjoyed our stay. Everything was perfect, close to Duval Street and everywhere we wanted to go!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Tracy S.

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

10/10 Excellent

Mike H.

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

8/10 Good

Glenn S.

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

Great location

For our short family spring break trip, the accommodations were great. Great location to everything we wanted to see and the amenities had all that we needed.
Stayed 3 nights in Mar 2022
Verified

8/10 Good

Melissa F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was walkable. Loved the front porch
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Lynne M.

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

Great location

Great location in walking distance
Stayed 6 nights in Apr 2022
Verified

10/10 Excellent

John B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved it!!
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

John P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communication. Clean property. Easy to walk to most things.
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Brianna B.

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

8/10 Good

Kathy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Apr 2026
Verified

10/10 Excellent

jim m.

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

nice place

great place with location. Beds were very comfortable. nice furnishings.
Stayed 4 nights in Nov 2021
Verified

10/10 Excellent

Kimberly O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a really nice stay. Property Manager was wonderful and receptive. No issues at all. Would definitely recommend.
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Dave S.

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

Good location

The property owner and staff do a great job of communicating. House is very clean and worked well for us
Stayed 3 nights in May 2025