Entertainment events in Key West
Check out happening entertainment events all around Key West, FL
Duval Street Party with the Landshark Band
Fri, 04 Sep at 06:00 pm
200 Duval St, Key West, FL 33040, United States
28th Annual Key West Lobsterfest
Wed, 05 Aug at 06:00 pm
100-500 Blocks Duval Street, Key West, FL, United States, Florida 33040
Mangoes Drag Brunch Royale Pride Week
Sun, 07 Jun at 11:30 am
Mangoes Restaurant
USD 55 to 66
FLO-RAW at Sloppy Joes Key West
Sat, 04 Jul at 10:00 pm
Sloppy Joe's Bar
Mangoes Drag Brunch Royale Halloween Edition
Sun, 01 Nov at 11:30 am
Mangoes Restaurant
USD 55 to 66
Second Line Memorial Walking Parade
Sun, 06 Sep at 05:00 pm
100 Duval St, Key West, FL 33040-6506, United States
Paint the Town Proud Trolley Pub Roll
Sat, 06 Jun at 11:00 am
Bobby's Monkey Bar
Key West OktoBREWfest
Sat, 03 Oct at 03:00 pm
1319 Duval Street, Key West, FL, United States, Florida 33040
The Rotary Club of Key West Casino Night Roaring 20's Speakeasy
Sat, 16 May at 06:30 pm
Beachside Key West
Back to the Island Beach Party
Sat, 05 Sep at 11:00 am
801 Bourbon bar
Key West Pride Follies
Sat, 30 May at 07:30 pm
Key West Theater
Lobsterfest Kick-Off Party at Rick's
Wed, 05 Aug at 07:00 pm
Rick's Key West
Just a Few Friends Celebration, Key West
Thu, 03 Sep at 11:00 am
Key West
John Caparulo in Key West, FL!
Thu, 28 May at 08:30 pm
Comedy Key West
Follow The Rabbit... (9PM)
Fri, 29 May at 09:00 pm
Key West Theater
Parrots and Margaritas 5k Run/Walk
Sat, 05 Sep at 08:00 am
Kaya Island Eats
The Wheeland Brothers + Mike Stack & Friends at Sunset Pier
Sat, 05 Sep at 06:30 pm
Sunset Pier, Key West, FL 33040, United States
Garrison Keillor (21+)
Wed, 28 Oct
Key West Theater
Florida Keys Mini Season Getaways! (MarineMax St. Pete) - Waitlisted
Sat, 25 Jul at 10:00 am
The Perry Hotel & Marina Key West
Free
Mango Madness Summer Members' Exhibit Opening
Thu, 04 Jun at 06:00 pm
533 Eaton St, Key West, FL, United States, Florida 33040
2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"!
Sat, 31 Oct at 04:00 pm
Sebago Watersports
International Ocean Film Festival (Florida Keys Viewing)
Sat, 06 Jun at 05:30 pm
Williams Hall
Gypsies In The Palace Buffett Tribute Band at Hogs Breath
Sat, 05 Sep at 04:30 pm
Hog's Breath Saloon
Wheeland Brothers in Key West
Sat, 05 Sep at 07:00 pm
Sunset Pier
The BIG Pride Fundraiser
Thu, 25 Jun at 05:00 pm
504 Angela St, Key West, FL 33040-7433, United States
Through the Lens – Early Buffett Concert Photography Exhibit Meet & Greet
Fri, 04 Sep at 04:15 pm
Pier House Resort & Spa
Outdoor Movie: Parrot Heads – The Essential Jimmy Buffett Documentary
Fri, 04 Sep at 09:00 pm
Southernmost Pint Brewpub
Sister Season's Aqua Idol
Tue, 28 Apr at 06:00 pm
AquaPlex Key West
A Pirate Looks Back, the Key West Jimmy Buffett Tribute Show
Wed, 02 Sep at 12:30 pm
218 Whitehead St, Key West, FL 33040-6595, United States
2026 - Friday, Oct. 30 - Jerry Diaz's Key West Sunset "Booze Cruise"
Fri, 30 Oct at 05:00 pm
Sebago Watersports
Pool Party at La Concha
Mon, 07 Sep at 01:00 pm
La Concha Key West
Island Groove Dance Studio Presents: Be Our Guest
Sun, 17 May at 04:30 pm
Key West High School
The Marshall Morlock Band: Summer Send-Off
Fri, 19 Jun at 08:00 pm
Key West Theater
“Open Mic / No Mic Night” at Andy's Cabana
Thu, 03 Sep at 07:00 pm
Andy's Cabana
Friends of Bubba Outdoor Video Lounge
Sat, 05 Sep at 08:30 pm
Southernmost Pint Brewpub
Sunset to Stage: Wheeland Brothers Dockside Party
Sat, 05 Sep at 08:00 pm
S/V Argo Navis
Key West Murder Mystery 2: Crime on Date Night!
Mon, 01 Jun at 12:00 am
502 Whitehead St, Key West
USD 15
Key West or BUST!
Sat, 30 May at 11:00 am
Key West, Florida
Stars, Stripes & Sandbars Getaways! | July 3-6, 2026
Fri, 03 Jul at 08:00 am
Galleon Marina
Free
Landsharks Band, Key West Concert, JUST A FEW FRIENDS CONCERT WEEKEND!
Fri, 04 Sep at 05:00 pm
Key West
The Key Lime Festival Kick Off Party & SPIRIT Pageant!
Wed, 01 Jul at 05:00 pm
1317 Duval St, Key West, FL 33040-3131, United States
Cypress Gardens Water Ski Show
Sat, 16 May at 02:00 pm
Cypress Gardens Water Ski Team (est. 2012)
Kids Music Tour Key West Florida
Mon, 15 Jun at 10:00 am
Key West Public Library
"Shrimp Boat Sound: Echoes From the Edge" Movie Panel Discussion
Fri, 04 Sep at 02:30 pm
729 Fleming St, Key West, FL 33040-6827, United States
Through the Lens – Early Buffett Concert Photography Exhibit
Sat, 05 Sep at 08:00 am
Pier House Resort & Spa
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Events in Key West
Entertainment events in Key West