Best Live Music in Key West

Real videos of Live Music in Key West — 5 places, filmed by creators on the ground.

Ranked venues

Willy T’s
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FestiveLivelyWelcomingSeafood menuLive musicOpen-air design
About the venue
Willy T's, another establishment on Duval Street, focuses on a vibrant dining experience with live music and an engaging atmosphere. It offers a menu filled with seafood specialties, such as fish tacos and conch fritters, alongside a robust drinks menu. The bar's open-air layout makes it ideal for enjoying warm evenings in Key West. It's a well-loved spot for both locals and tourists seeking a festive night out.
What the videos show
A man performs an acoustic guitar song in a uniquely themed indoor space featuring a ceiling entirely covered in dollar bills and various decorative signs. The camera pans to reveal a bar area with seated patrons, suggesting a lively nightlife setting. The performance begins at 0:00 with the lyrics 'You can put me out on the street, you can put me out,' setting a reflective, slightly defiant tone. The setting appears to be a themed bar or lounge, possibly a speakeasy or entertainment venue, with strong visual storytelling and a clear atmosphere. The video captures a real-world experience that viewers could potentially visit, book, or attend, with a distinct identity and immersive environment.
525 Duval St
@gotamarble
Sloppy Joe's Bar
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$$LivelyHistoricFestiveLive musicSignature SloppyOutdoor seating
About the venue
Sloppy Joe's Bar has been a Key West institution since 1933, known for its lively atmosphere and rich history associated with Ernest Hemingway. The bar offers a vibrant beach-themed setting, complete with outdoor seating and a stage for live music performances. Guests can enjoy the signature Sloppy Joe sandwich alongside a variety of tropical cocktails. With daily live entertainment, it attracts a mix of locals and tourists, making it a go-to spot for nightlife in the area.
What the videos show
The video showcases a lively bar scene with patrons seated at tables, some engaged in conversation while others are looking at their phones. A band is performing on stage, adding to the vibrant atmosphere.
201 Duval St
@Lakeslover
@cierralynn
Willie T's
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$$VibrantLivelyTropicalLive musicSeafood menuOutdoor seating
About the venue
Willie T's is a lively bar and restaurant located on Duval Street in Key West, notable for its vibrant atmosphere and live music events. It features a diverse menu that highlights seafood dishes and tropical cocktails, making it a popular spot for tourists and locals alike. The outdoor seating area offers views of the bustling street, allowing patrons to experience the local nightlife. Established in 1996, it is known for its welcoming charm and party vibe.
What the videos show
The video showcases a man sitting on a stool, playing an acoustic guitar and singing into a microphone at Willie T's bar. The setting includes a wall decorated with dollar bills and a sign that reads 'Willie T's.' The camera remains stationary, capturing the performer's actions and the ambiance of the venue.
525 Duval St
@amber_olive25
Key West Sunset Cruise
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RelaxingScenicSocialSunset viewsLive music2-hour cruise
About the venue
Key West Sunset Cruise departs from 2 Duval Street in Key West and offers a scenic sailing experience around the island at sunset. Guests are treated to stunning views of the sun setting over the water, often accompanied by live music and refreshments on board. This popular cruise allows for an immersive experience of Key West's natural beauty, making it a favorite among tourists and locals alike. The excursion typically lasts about 2 hours and provides photo opportunities and relaxation.
What the videos show
The video showcases Sunset Pier, a vibrant outdoor dining and nightlife spot. It captures the sunset ambiance with diners enjoying food and drinks under umbrellas, patrons socializing, and a live band performing on a stage. The pier is decorated with string lights, and the camera pans across various scenes, including people at tables, inside the bar area, and a couple engaged in conversation.
2 Duval St
@Julimaimi
Angelina's Pizzeria
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$$CasualFamily-friendlyLocal favoriteNew York-styleFamily-runFriendly service
About the venue
Angelina's Pizzeria in Key West is renowned for its New York-style pizza piled high with quality ingredients. Nestled on Duval Street, this family-run restaurant has been serving customers since 2017, offering a casual dining atmosphere perfect for families and groups. The menu features a wide selection of specialty pizzas and classic Italian dishes. Known for its friendly service, Angelina's is a favorite among both tourists and locals.
What the videos show
The video captures a bald man playing a white electric guitar on stage under blue lighting. The background includes a drum set labeled 'The Durtbags' and other musical equipment, with the camera remaining static throughout the clip.
208 Duval St
@cierralynn