Entire home·Private host

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

Cottage with kitchen, 3-minute walk to Duval Street

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

Beach nearby
Exterior
Fridge, microwave, oven, stovetop
Smart TV
3 bedrooms, iron/ironing board, free WiFi, bed sheets
In the heart of downtown Key West, the Southernmost Retreat is a charming 3-bedroom house within walking distance to beaches and Old Town District attractions. Enjoy new HIDEF Samsung 4K Smart TVs in each bedroom and living room, FREE high-speed internet, brand-new central air conditioning system for ultimate comfort.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 670 sq m

Popular amenities

  • Parking available
  • Pet-friendly
  • Barbecue grill
  • Kitchen
The current price is €601
includes taxes & fees
17 Nov - 18 Nov

Add dates for prices

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. There is a grill outside in the courtyard for you to use.

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.



Property amenities

Beach

  • Beach nearby

Internet

  • Available in the cottage: Free WiFi

Parking and transport

  • Parking on site

Kitchen

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

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

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

Living spaces

  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Outdoor furniture
  • Patio

Laundry

  • Laundromat nearby

Comfort

  • Air conditioning

Pets

  • Pet friendly
  • Welcoming dogs only
  • Up to 9 kg per pet

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • 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
  • Snorkelling nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • 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 and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM
Contactless check-out

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total (up to 9 kg per pet)
Restrictions apply; for more information contact the property on the number on the booking confirmation
Note from host: must be under 20 pounds

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
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

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

About the area

Map
Key West, FL

What's nearby

  • Duval Street - 3 min walk - 0.3 km
  • Ernest Hemingway Home and Museum - 5 min walk - 0.4 km
  • South Beach - 8 min walk - 0.7 km
  • Southernmost Point - 9 min walk - 0.8 km
  • Mallory Square - 18 min walk - 1.5 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 9 min drive

Restaurants

  • ‪Old Town Tavern - ‬4 min walk
  • ‪801 Bourbon Bar - ‬6 min walk
  • ‪Vinos on Duval - ‬5 min walk
  • ‪Viva Argentinian Steakhouse - ‬4 min walk
  • ‪Nine One Five - ‬3 min walk

Frequently asked questions

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

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 9 kg per pet. Some restrictions may apply, so please contact the property for more details.

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

As of 6 Nov 2025, prices found for a 1-night stay for 2 adults at The Dancing Rooster: 2 Blocks from Duval in Old Town. on 17 Nov 2025 start from €601.38, 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.

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.?

Checkout 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. Ernest Hemingway Home and Museum and Florida Keys Beaches are also within 10 minutes.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 117 out of 128 reviews
Rating 8 - Good. 11 out of 128 reviews
Rating 6 - Okay. 0 out of 128 reviews
Rating 4 - Poor. 0 out of 128 reviews
Rating 2 - Terrible. 0 out of 128 reviews

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

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

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

10/10 Excellent

Suzanne D.

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

10/10 Excellent

Cecile S.

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

10/10 Excellent

Verified traveller

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

10/10 Excellent

lori D.

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

Key West triathlon

Perfect location for us!
Stayed 3 nights in Dec 2021

10/10 Excellent

Susan H.

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

Excellent!

Would highly recommend this property!
Stayed 6 nights in Feb 2022

10/10 Excellent

Richard C.

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

Key west one night

Very nice and comfortable
Stayed 1 night in Jan 2024

10/10 Excellent

Keith P.

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

Thanksgiving week shenanigans

Comfy beds, clean sheets. Parking was as described. No spot the first night and had to move the car the next morning. Nice central location just off Duval.
Stayed 3 nights in Nov 2024

10/10 Excellent

Ginger W.

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

Great stay, book here

Small but cozy. It was very good for our family, especially my 80 year old parents. It had everything we needed and the location was perfect. Nancy was very responsive to our questions. We would stay here again in a heartbeat.
Stayed 4 nights in Feb 2023

10/10 Excellent

Andi B., Annapolis, MD

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

Highly recommended

Everything about this place exceeded our expectations! The location was ideal for us to walk to everything (water sports, shopping, dining, historical locations, etc). The bungalow is beautiful and cozy! It is close enough to the “action” and still far enough for serenity!! You can’t go wrong with this place!!
Stayed 4 nights in May 2022

10/10 Excellent

Michelle B.

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

Excellent location!

This house was as advertised. We stayed for 5 days at this location and it was close to Duval but yet it was very quiet of a night and there wasn’t any disturbances that kept us up. House was clean and nice. Would definitely recommend!
Stayed 5 nights in Jul 2022

10/10 Excellent

Michele H.

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

Great location!

Great little place in a great location just a block off Duval. Scott and Natalie were more than accommodating and very attentive to any questions I had. Parking was a little tricky but it's Key West so that was to be expected. We had a great weekend! Would definitely stay here again!
Stayed 3 nights in Oct 2021

10/10 Excellent

phyllis k.

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

Perfect in paradise ❤️

I stayed here with my elderly parents , my hubby and I and my parents. Location is 1 block from CVS and 1 1/2 block from MANY GREAT restaurants.The beds were comfortable and the AC worked great( very important in the Keys😁).I had a last minute change with my booking and Scott , the owner , was VERY helpful .I visit the Keys yearly and hope to stay here next year again.The cottage is WONDERFUL and clean… Thanks for a great STAY😁
Stayed 3 nights in Jun 2021

10/10 Excellent

Mike P.

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

Close to Duval

Walking close to Duval. On street parking can be tough but this block is NOT pay to park! Good to know.
Stayed 4 nights in May 2024

10/10 Excellent

jeanne b.

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

Very clean and convenient location.

Communication was excellent with Nancy. We were able to leave our luggage and come back later to check in. Milton, the housekeeper was accommodating and friendly. This cottage is a block from Duvall and we walked everywhere with no problem. Will def return and stay here. Thanks for having us!! : )
Stayed 1 night in Oct 2023

10/10 Excellent

Gilbert W., Bentonville, AR

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

New Year’s Eve in Key West Style

The cottage was in the perfect location… 2 blocks off Duval. Loved the outdoor seating. Several mornings we went to the French Bakery on Duval to get breakfast and brought it back to enjoy outside. The cottage was perfect for our group. The only thing I would say is the mattresses are probably at end of life 😊. New softer mattresses and this place is 10’s across the board. Thank you for sharing your cottage
Stayed 5 nights in Dec 2022

10/10 Excellent

Sheila F.

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

So Very Convenient

This was our first family vacation which included our son in law. The set up was perfect the adult children took the rooms with the queen beds and shared the bath; my husband and I took the smaller room with the full bed and enjoyed our ensuite. It was so close to Duvall Street that everything was easily accessible, but not so close that we were disturbed by the noise. We will definitely stay there again if we have that many people. There was a problem with the smoke detector one night, but Nancy was quick to respond, and the problem was easily resolved.
Stayed 5 nights in Jul 2023

10/10 Excellent

Amy P.

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

Perfect location and clean

Hafa adai, I’ve spent a lot of time in key west since my father used to live here. There’s a fine balance in picking a location that is close to the action but not so close that you’ll be kept up all night. This is prime location in my eyes. One street away from duval and couple blocks to the left for morning breakfast and few more right to hit shopping then bars. The house appeared to be recently renovated. Had literally everything we expected and needed. Full kitchen with coffee pot and wine glasses, TVs in every room, and 3 bedrooms that could sleep 2 people in each room easy. Anytime we needed assistance the property manager answered immediately. Had a wonderful time on my 40th birthday with my family here and would recommend and stay again.
Stayed 3 nights in Jul 2021

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

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

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

10/10 Excellent

Carol M.

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

10/10 Excellent

Gerrilynne S.

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

N/a

Great location
Stayed 3 nights in Feb 2025

10/10 Excellent

Kevin C.

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