Condo

BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

Photo gallery for BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

A brick pathway leading to a white staircase with a covered area above.
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.
A bar area with a wooden bar counter, multiple stools, and a variety of bottles and glasses.
A bedroom with a bed, two bedside lamps, a ceiling fan, and three large wall-mounted pictures.
A white building with a balcony, palm trees, and flags.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Discover nearby landmarks
    Near Duval Street

Popular amenities

  • Air-conditioning
  • Refrigerator
  • Onsite parking available
  • Internet
  • Non-smoking
  • Microwave

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, South Beach
    ‪3 min walk‬
  • Place, Southernmost Point
    ‪5 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 Queen Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Add dates for prices

Similar properties

Terrace/patio
Elegant Condo with Entertainment & Private Parking - Great Central Location
Old Town Key West
  • Kitchen
  • Air-conditioning
  • Parking available
  • Microwave
8.8 out of 10, Excellent, (164 reviews)
Elegant Condo with Entertainment & Private Parking - Great Central Location

About the area

Key West

Located by the sea, this condo 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 Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Key West Butterfly and Nature Conservatory and Florida Keys Eco - Discovery Center are also worth visiting. Discover the area's water adventures with scuba diving, snorkelling and sailing nearby, or enjoy the great outdoors with cycling.
Map
Key West, FL

What's nearby

  • Duval Street - 1 min walk - 0.0 km
  • South Beach - 3 min walk - 0.3 km
  • Key West Butterfly and Nature Conservatory - 3 min walk - 0.3 km
  • Ernest Hemingway Home and Museum - 4 min walk - 0.4 km
  • Southernmost Point - 5 min walk - 0.4 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 12 min drive

Restaurants

  • ‪Circle K - ‬1 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬1 min walk
  • ‪Southernmost Point Bar in the USA - ‬4 min walk
  • ‪Old Town Tavern - ‬4 min walk
  • ‪Banana Cafe - ‬1 min walk

Frequently asked questions

Is BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?

As of 10 Nov 2026, prices found for a 1-night stay for 2 adults at BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! on 11 Nov 2026 start from £213, 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 BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?

On-site parking is available at the property.

What time is check-in at BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?

Check-in begins at 3:00 PM.

What time is check-out at BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?

Checkout is at 11:00 AM.

Where is BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! located?

Located in Old Town Key West, this condo building is steps away from City Zoo Gallery and Duval Street. Florida Keys Beaches and South Beach are also within 5 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 9 out of 10 reviews
Rating 8 - Good. 1 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Friendly people, our room was clean and so homey (room 2 - second floor). No noise from bar on first floor. We walked to most everything, some things we did use uber. It was hot - August, so uber to restaurant at the wharf and walked back.
Stayed 4 nights in Aug 2026
Response from Management on 26 Oct 2026
We’re so glad you had a great time with us. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
From a partner site

10/10 Excellent

Cozy spot to rest

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Comfortable bed, clean space, well equipped kitchenette & COLD AC. This particular room is small and without any seating, but a very comfortable place to clean up & rest after long days exploring Key West. Very convenient Duval St location on the quiet end, but just a few blocks from the action.
Response from VrboOwner on 29 Jul 2026
Thanks so much for the lovely feedback! We’re happy to hear you enjoyed the property and would love to host you again in the future.
From a partner site

10/10 Excellent

Just the weekend getaway room we needed!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Couldn't have been happier! The Bootlegger Bay Suite was just enough room for 2, clean, well appointed, and quiet (especially considering its only a couple doors down the path from the Rum Bar!). Great atmosphere all around. The personal consierge service was invaluable and a great touch! Easy 5 minute walk to the Southernmost Point, and maybe 15 minutes to walk to Mallory Square.
Response from VrboOwner on 4 Nov 2026
We’re grateful for your glowing review! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
From a partner site

10/10 Excellent

In the middle of all the action!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very good experience. The owners/management company was wonderful! Could walk to everythin, including the ferry that goes to Dry Torgogus, as well as the airport.
Response from VrboOwner on 14 Feb 2026
It makes us so happy to know you had a great time as our guest Debbie! We loved having you as our treasured guest and hope to see you again!
From a partner site

8/10 Good

Fantastic location! Right on Duval!

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The location of this little room was behind the Rum Bar (very good drinks!) and a fun place to stay. However, the room was very small. It was hard for just two of us to get around in the room. I realize that a lot of places in KW are small, but I would have gotten something bigger if I did it again. It was clean. Communication was excellent!
Response from VrboOwner on 30 Oct 2026
We’re so glad you had a great time with us. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent stay! The property was exactly what we were looking for. The location was perfect—within walking distance of great restaurants, bars, and nightlife, making it easy to enjoy the area without needing to drive.. The attached bar gives the property a good vibe. The accommodations were comfortable, clean, and well-maintained. We had a wonderful stay and would definitely book this property again.
Stayed 3 nights in Apr 2026
Response from VrboOwner on 17 Jun 2026
We’re so glad you had a great time with us Kortnie. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
Verified review

10/10 Excellent

Stayed 3 nights in Sep 2026
Response from Management on 27 Oct 2026
We appreciate the stellar rating! Thank you and please come back again soon!
Verified review

10/10 Excellent

Stayed 3 nights in Jun 2026
Response from VrboOwner on 3 Aug 2026
Thank you for the excellent rating! We are delighted you had a great experience and look forward to welcoming you back!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 4 nights in May 2026
Response from VrboOwner on 30 Jun 2026
Thank you for the excellent rating Thomas! We appreciate it and hope you'll return soon as our guest!
Tell us how we can improve our siteShare feedback