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
9.89.8 out of 10
Exceptional
Entire home
3 bedrooms2 bathroomsSleeps 670 sq m
Popular amenities
Kitchen
Pet-friendly
Outdoor space
Parking available
The current price is AU$979
AU$979
includes taxes & fees
13 Apr - 14 Apr
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.
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
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
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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 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
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
We should mention
This property does not have any lifts
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
Located near the beach, this cottage is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with ecotours and cycling. Visit our Key West travel guide
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 21 Mar 2026, prices found for a 1-night stay for 2 adults at The Dancing Rooster: 2 Blocks from Duval in Old Town. on 13 Apr 2026 start from AU$979, 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.
How much is parking at The Dancing Rooster: 2 Blocks from Duval in Old Town.?
On-site 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.?
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
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.
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!
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.
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
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.
Excellent location. Wrought can walk to just about anywhere you want to on the island. 4 of us stayed in the 3 BR house. 6 people would have been a very tight fit. Bedrooms are small. Tight fit for 2 suitcases. Beds were soft. Pillow's were flat. 2 ice trays in small freezer, so go to CVS down the street to purchase ice. 1bath towel per person for our 6 day stay, which was inadequate in this tropical environment. Both bathrooms ran out of toilet paper. We all really enjoyed being able to sit outside on the front patio. There was room for all 4 of us.
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.
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.
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.
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.
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.
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.
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!
It was really important for my group to be able to walk to the majority of the food and things. It was a great spot to do that from. Our only regret is we did not come during a time of year when the weather was touch warmer.
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.
We attended a friends wedding with 6 of us staying at the Southernmost Retreat. Great central location close to everything, plenty of room in the cottage for all of us and ice cold air conditioning for that hot Key West weather. We had a great time and would stay again.
The home was a great option vs three hotel bookings, centrally located we walked to all adventures on Duvall St, stayed for one night for cinco de mayo, beds were great showers etc all good
This was in the perfect location: not too far from Mallory Square or the buoy. Close to Duval yet in a quieter neighborhood. Parking is an issue but it was pointed out before we booked the trip so we were prepared. We loved it! We would stay there again and also highly recommend it to other travelers! A+