The Dancing Rooster: 2 Blocks from Duval in Old Town.
Select date
-
Select date
1 night
All properties in Key West

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

Key West, Florida, 33040
Show on map
Complete address will show after booking
We Price Match
hotel overview picture
Amenities
Golf course
Snorkeling
Wi-Fi in public areas
BBQ
No smoking in public areas
Kayaking
Parasailing
Sailing
All amenities
Property Description
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. About pets:Pets allowed: dogs less than 20 lbs per pet (limit one pet total).Must be under 20 pounds.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Show more
9.8/10
Outstanding
Cleanliness9.8
Amenities9.8
Location9.8
Service9.8
All 56 reviews
Surroundings
Airport: Key West International Airport
(5.7 km)
Landmarks: The Hemingway Home and Museum
(250m)
View on map

Overview

Rooms

Guest Reviews

Services & Amenities

Policies

Host

10

Three-Bedroom Cottage

3 bedrooms: 2 queen beds and 1 double bed
Non-smoking
Room Details
Check Availability

Guest Reviews

9.8/10
Outstanding
56 reviews
Verified Reviews
  • Cleanliness9.8
  • Amenities9.8
  • Location9.8
  • Service9.8
Average for similar properties in Key West
Most Mentioned
K‍r‍i‍s‍t‍i
October 9, 2025
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.
K‍i‍m‍b‍e‍r‍l‍y‍ ‍O‍.
September 24, 2025
We had a really nice stay. Property Manager was wonderful and receptive. No issues at all. Would definitely recommend.
J‍o‍h‍n‍ ‍P‍.
October 17, 2025
Great communication. Clean property. Easy to walk to most things.
D‍a‍v‍e‍ ‍S‍.
May 13, 2025
Good location The property owner and staff do a great job of communicating. House is very clean and worked well for us
T‍r‍a‍c‍y‍ ‍S‍.
May 12, 2025
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!
C‍a‍r‍o‍l‍ ‍M‍.
April 25, 2025
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
C‍e‍c‍i‍l‍e‍ ‍S‍.
March 11, 2025
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.
V‍e‍r‍i‍f‍i‍e‍d‍ ‍t‍r‍a‍v‍e‍l‍e‍r
March 17, 2025
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.
S‍u‍z‍a‍n‍n‍e‍ ‍D‍.
March 31, 2025
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.

Services & Amenities

More Amenities
Internet
Public areas
Health & wellness
Activities

Property Policies

Check-in and Check-out Times
Check-in: after 16:00
Check-out: Before 11:00
Child policies
Children of all ages are welcome at this property.
Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.

Cribs and Extra Beds
Please contact the hotel for details about crib and extra bed policies.

Age Requirements
The main guest checking in must be at least 25 years old

Property host

Scott Miller
Speaks: English, Spanish

About this property

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. About pets:Pets allowed: dogs less than 20 lbs per pet (limit one pet total).Must be under 20 pounds.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Show Full Description

Frequently Asked Questions

What’s the cancellation policy at The Dancing Rooster: 2 Blocks from Duval in Old Town.?

The cancellation policy at The Dancing Rooster: 2 Blocks from Duval in Old Town. depends on your room type and booking terms.

What are the check-in and check-out times at The Dancing Rooster: 2 Blocks from Duval in Old Town.?

Check-in at The Dancing Rooster: 2 Blocks from Duval in Old Town. starts from 16:00, and the standard check-out time is by 11:00.

How do I get to The Dancing Rooster: 2 Blocks from Duval in Old Town. from the nearest airport?

The nearest airport is Key West International Airport, located about about 12 mins from hotel by car (5.7 km) away.

About This Property

Nearest AirportKey West International Airport
Distance to Airport5.65KM
Hotel Star Rating3