Key West Comedy Shows 2026
Stand-up comedy, touring comedians, and live comedy shows in Key West and nearby areas.
- Updated: November 15, 2026
Browse comedy shows in Key West, FL this year, including stand-up, touring comedians, improv, and club performances. Explore shows by date and venue, with schedules updated regularly as new comedians and events are announced.
- 26 Upcoming Shows
- 0 This Weekend
- Next Show Starts In:
- Greg Fitzsimmons
- Nov 18 · 8:00 PM · Key West, FL
- View Tickets
Best Comedy This Week & This Month
Featured comedy shows and stand-up comedians in Key West and surrounding areas.
Comedy Shows By Dates
Upcoming Comedy Shows
Explore stand-up comedians, comedy tours, and live comedy performances by date and venue in Key West.Comedy Shows: 26
- Nov 18, 2026, 8:00 PM Wed — COMEDY, Best Value: Greg Fitzsimmons at Comedy Key West,
218 Whitehead St, Key West, FL 33040, US. From $56, Avg. price ~ $66, 22 tickets remaining! Select Seats - Nov 19, 2026, 8:00 PM Thu — COMEDY, Best Value: Greg Fitzsimmons at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $56, Avg. price ~ $66, 22 tickets remaining! Select Seats
- Nov 20, 2026, 8:00 PM Fri — COMEDY, High Demand: Dusty Slay at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $65, Avg. price ~ $403, Tickets Available: 150. Select Seats
- Nov 20, 2026, 8:00 PM Fri — COMEDY, Best Value: Greg Fitzsimmons at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $56, Avg. price ~ $66, 22 tickets remaining! Select Seats
- Nov 21, 2026, 8:00 PM Sat — COMEDY, Best Value, Weekend Event: Greg Fitzsimmons at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $56, Avg. price ~ $66, 22 tickets remaining! Select Seats
- Nov 21, 2026, 8:00 PM Sat — COMEDY, High Demand, Weekend Event: Dusty Slay at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $65, Avg. price ~ $347, Tickets Available: 188. Select Seats
- Jan 13, 2027, 8:00 PM Wed — COMEDY, Best Value: Luis J. Gomez - Comedian at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 22 tickets remaining! Select Seats
- Jan 14, 2027, 8:00 PM Thu — COMEDY, Best Value: Luis J. Gomez - Comedian at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 22 tickets remaining! Select Seats
- Jan 15, 2027, 8:00 PM Fri — COMEDY, Best Value: Luis J. Gomez - Comedian at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 22 tickets remaining! Select Seats
- Jan 16, 2027, 8:00 PM Sat — COMEDY, Best Value, Weekend Event: Luis J. Gomez - Comedian at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 22 tickets remaining! Select Seats
- Jan 21, 2027, 8:00 PM Thu — COMEDY: Tom Papa at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $69, Avg. price ~ $92, Tickets Available: 189. Select Seats
- Jan 22, 2027, 8:00 PM Fri — COMEDY: Tom Papa at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $67, Avg. price ~ $91, Tickets Available: 191. Select Seats
- Feb 17, 2027, 8:00 PM Wed — COMEDY, Best Value: Lenny Clarke at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 20 tickets remaining! Select Seats
- Feb 18, 2027, 8:00 PM Thu — COMEDY, Best Value: Lenny Clarke at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 22 tickets remaining! Select Seats
- Feb 19, 2027, 8:00 PM Fri — COMEDY, Best Value: Lenny Clarke at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 22 tickets remaining! Select Seats
- Feb 20, 2027, 8:00 PM Sat — COMEDY, Best Value, Weekend Event: Lenny Clarke at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 22 tickets remaining! Select Seats
- Feb 25, 2027, 8:00 PM Thu — COMEDY, Best Value: Mary Mack at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $53, Avg. price ~ $80, 22 tickets remaining! Select Seats
- Feb 26, 2027, 8:00 PM Fri — COMEDY, Best Value: Mary Mack at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $53, Avg. price ~ $80, 22 tickets remaining! Select Seats
- Feb 27, 2027, 8:00 PM Sat — COMEDY, Best Value, Weekend Event: Mary Mack at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $53, Avg. price ~ $80, 22 tickets remaining! Select Seats
- Feb 27, 2027, 8:00 PM Sat — COMEDY, High Demand, Weekend Event: Paul Mecurio at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $71, Avg. price ~ $128, Tickets Available: 240. Select Seats
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Comedy Shows by Month
Monthly pages help you find upcoming comedy shows by season, weekend, and date.
All Comedy Shows in Key West
Browse stand-up comedians, comedy tours, and live comedy performances happening across Key West and nearby areas.
Greg Fitzsimmons
218 Whitehead St, Key West, FL 33040
Upcoming Shows: 14
Nov 18, 2026 8:00 PM
Dusty Slay
512 Eaton St., Key West, FL 33040
Upcoming Shows: 48
Nov 20, 2026 8:00 PM
Luis J. Gomez - Comedian
218 Whitehead St, Key West, FL 33040
Upcoming Shows: 11
Jan 13, 2027 8:00 PM
Tom Papa
512 Eaton St., Key West, FL 33040
Upcoming Shows: 6
Jan 21, 2027 8:00 PM
Lenny Clarke
218 Whitehead St, Key West, FL 33040
Upcoming Shows: 7
Feb 17, 2027 8:00 PM
Mary Mack
218 Whitehead St, Key West, FL 33040
Upcoming Shows: 4
Feb 25, 2027 8:00 PM
Paul Mecurio
512 Eaton St., Key West, FL 33040
Upcoming Shows: 2
Feb 27, 2027 8:00 PM
Kevin Bozeman
218 Whitehead St, Key West, FL 33040
Upcoming Shows: 7
Mar 04, 2027 8:00 PM
Dave Smith
218 Whitehead St, Key West, FL 33040
Upcoming Shows: 19
Apr 08, 2027 8:00 PM
Comedy Clubs & Venues
Explore comedy clubs, theatres, and venues hosting stand-up comedians and live comedy performances in Key West and nearby areas.
Comedy Shows FAQ
Quick answers about stand-up comedians, comedy tours, and live comedy performances happening in Key West.
What comedy shows are happening in Key West?
Comedy schedules may include stand-up comedians, touring comedy acts, improv performances, podcast tours, and live comedy specials across Key West and nearby areas.
Are comedy schedules updated regularly?
Yeah. New comedy performances and additional tour dates are added often as venues announce updated schedules and special events.
What types of comedy performances are included?
You’ll commonly find stand-up comedy, improv shows, podcast recordings, sketch comedy, and performances by touring comedians.
Where are comedy shows usually performed in Key West?
Comedy events are often hosted at comedy clubs, theatres, casinos, bars, resorts, and entertainment venues throughout Key West.
Do comedy shows happen during the week?
Absolutely. Many comedy venues host performances throughout the week, while weekends are usually the busiest nights for live comedy.
Do major comedians tour through Key West?
Yes. National touring comedians and comedy acts regularly perform in Key West throughout the year.
Explore More Events in Key West
Discover concerts, sports, theatre, family shows, festivals, and live entertainment happening across Key West and nearby areas.
comedy shows
26 Upcoming Events