Entire home

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

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

Beach nearby
Exterior detail
Exterior
3 bedrooms, iron/ironing board, free WiFi, bed sheets
Terrace/patio

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 670 sq m

Popular amenities

  • Kitchen
  • Pet-friendly
  • Outdoor space
  • Parking available

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.)
    ‪14 min drive‬

Room options

Similar properties

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.
This cottage's walkable location gets good marks from our customers. During your stay, you're just a quick walk from Duval Street. The cottage offers free WiFi and a kitchen.
  • Air-conditioned cottage with kitchen, 2 bathrooms and patio
  • Free WiFi
  • Just a 3-minute walk from Duval Street and 8 minutes on foot from Florida Keys Beaches
The Dancing Rooster: 2 Blocks from Duval in Old Town. offers its guests barbecue grills. The front desk is open around the clock.

This Key West cottage is smoke free.


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

  • No lift
  • 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 (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 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
Information provided by the property may be translated using automated translation tools

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 (weight limit: 20 lb per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees.
  • 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 indicated that there is a carbon monoxide detector on the property
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

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

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 129 out of 144 reviews
Rating 8 - Good. 14 out of 144 reviews
Rating 6 - Okay. 1 out of 144 reviews
Rating 4 - Poor. 0 out of 144 reviews
Rating 2 - Terrible. 0 out of 144 reviews

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

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

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

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

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

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

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

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

John B.

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

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

Tammra B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a lovely visit. The cottage was lovely and great location. Had a minor issue (co2 detector) and the property manager was quick to take care of it for us so we could go on with our day. Turned out it just needed to be changed and really didn’t matter much because every room had a detector. Would highly recommend!!
Stayed 5 nights in Dec 2025
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

Christina C.

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

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

10/10 Excellent

Kristi

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

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

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

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

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
Verified

10/10 Excellent

Adam H.

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

10/10 Excellent

Robin E.

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

Perfect Location

Great accommodations close to everything. Extremely clean and surprisingly quiet.
Stayed 1 night in Feb 2023