The Key West, FL Live Music Guide
Listing figures generated 09-22-2026
Key West has live music along Duval Street, in Old Town bars and on the waterfront, with solo acts, duos and house bands playing afternoon and late-night sets. Check individual listings for times and admission details. Right now hapjam tracks 1 live-music venue across the areas listed below, with 52 shows on the calendar over the next 30 days — most listed in Key West, updated in real time as venues post and confirm their calendars.
Areas included: Key West.
This guide is the map: how the scene works, where to go by neighborhood, and who's on stage tonight. For a specific night, jump straight to live music by city.
A few shows happening tonight
Jon Hollywood
Irish Kevin's · Key West
11:00 AM – 2:30 PM
Andrew Burleson
Irish Kevin's · Key West
2:30 PM – 6:00 PM
NY Pauly
Irish Kevin's · Key West
6:00 PM – 10:00 PM
Riptide Riot
Irish Kevin's · Key West
10:00 PM – 2:00 AM
How the scene works
Cover. Admission varies by show. A missing cover charge does not mean free admission. Check the show's page for any listed price or ticket link, and confirm with the venue before heading out.
Season. Winter (roughly December–April) is peak season, and the festival calendar adds spikes: the songwriters festival in spring, Fantasy Fest in late October, and holiday weeks. Summer is quieter and hotter, but the bars keep music going year-round.
Where to go, by area
Each area links to its live schedule.
Key West
1 venue · 52 shows over the next 30 days
Spots include Irish Kevin's. See Key West's full schedule →
Acts with shows over the next 30 days
The performers with the most listed shows across the areas listed below.
Good to know
- Old Town is walkable — most of the music sits within a few blocks of Duval Street, so skip the car and go on foot or by bike.
- Sunset at Mallory Square is the nightly pivot: afternoon sets wind down, the evening rooms fill up.
- Bring a little cash if you'd like to tip the musicians.
- Lineups change often; follow a venue or act on hapjam to get a heads-up when they're playing.
Key West live music — FAQ
Is admission free at the shows in this guide?
Admission varies across the areas listed below. A missing cover charge does not mean free admission. Check each show's listed price or ticket link and confirm with the venue.
Where can I find tonight's shows?
See the shows above, or the live schedule by city — hapjam updates it as schedules change. The figures in this guide cover the areas listed below.
About this guide. Compiled by hapjam from published schedules across the areas listed below: 1 venues and 52 shows over the next 30 days, with figures generated 09-22-2026. Venue lists, counts, and tonight's shows are generated from published listings supplied by venues, performers or their public calendars; neighborhoods reflect where those venues actually are. Check individual listings for confirmation and changes.
Run a venue or play around Key West?
Claim your spot free — be on the map and the live feed, manage your own schedule, and reach fans searching for music tonight.