Entertainment events in Key West
Check out happening entertainment events all around Key West, FL
Mac McAnally in Key West
Fri, 05 Dec at 08:00 pm
Key West Theater
Key West Lighted Boat Parade 🎄
Sat, 13 Dec at 07:30 pm
631 Greene St, Key West, FL, United States, Florida 33040
HEART LIFE MUSIC: An Evening in Conversation with Kenny Chesney
Mon, 10 Nov at 07:30 pm
5901 College Rd, Key West, FL, United States, Florida 33040
DEADFEST KEY WEST - FALL SESSIONS - DEC 5th, 6th & 7th
Fri, 05 Dec at 03:00 pm
The Alamo Key West
1st Annual USCGC Ingham Fundraising Gala
Sat, 22 Nov at 05:00 pm
Truman Waterfront Park - West end of Southhard Street, Key West, FL, United States, Florida 33040
Glitter Witch Official Halloween Bar Crawl and Party
Fri, 31 Oct at 09:00 pm
504 Angela St, Key West, FL, United States, Florida 33040
The Garcia Project Key West
Wed, 05 Nov at 08:00 pm
Key West Theater 512 Eaton St Key West, FL, 33040
Mac McAnally in Key West
Sat, 06 Dec at 08:00 pm
Key West Theater
The Garcia Project: Performing classic Jerry Garcia Band Set Lists from 1976-1995
Sat, 15 Nov at 08:00 pm
512 Eaton St, Key West, FL, United States, Florida 33040
Shoreline Sessions Reggae Beach Festival
Sat, 01 Nov at 04:00 pm
1319 Duval Street, Key West, FL, United States, Florida 33040
Q West: Comedy Escape 2026
Fri, 10 Apr at 02:00 pm
Key West Theater
USD 450 to 534
Melon Jelly LIVE @ The Alamo, Key West FL 🎶
Fri, 21 Nov at 09:00 pm
The Alamo Key West
A work-in-progress preview screening of "The Life & Art of Eric Anfinson"
Sun, 16 Nov at 07:00 pm
533 Eaton St, Key West, FL, United States, Florida 33040
Scott Kirby- 35 Years of Songs & Stories
Thu, 26 Feb at 07:00 pm
Key West Theater
Wheeland Brothers
Sat, 08 Nov at 08:00 pm
Key West Theater
DINNER & A SHOW - TONY BALTIMORE makes you dinner!
Wed, 26 Nov at 08:00 pm
Key West Theater
Follow The Rabbit... (6PM)
Sat, 01 Nov at 06:00 pm
Key West Theater
Mac McAnally in Key West
Thu, 04 Dec at 08:00 pm
Key West Theater
The Brit Pack: The Ultimate British Music Experience
Sat, 17 Jan at 08:00 pm
Key West Theater
Running of the Elves
Sat, 20 Dec at 06:00 pm
Key West
Custom House Holiday Concert & Bazaar
Fri, 12 Dec at 05:00 pm
Key West Art & Historical Society
Freedom Flotilla Festival
Fri, 19 Dec at 05:00 pm
Key West, Floirda
Key West Theater Welcomes The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers
Sat, 29 Nov at 08:00 pm
Key West Theater
Freedom Flotilla Festival
Fri, 19 Dec at 05:00 pm
Key West
Free
Bali Bar Party
Fri, 07 Nov at 08:00 pm
325 Duval St, Key West, FL 33040-6565, United States
Keys Choral Arts: Holiday Concert
Sat, 13 Dec at 07:00 pm
Tennessee Williams Theatre
Ann Hampton Callaway - Finding Beauty: Inspired Classics and Originals
Mon, 17 Nov at 07:30 pm
Tennessee Williams Theatre
The Alamo KW Welcome Party
Mon, 03 Nov at 05:30 pm
4 Charles St, Key West, FL 33040-6504, United States
Performing for Key West Wedding
Sat, 29 Nov at 04:00 pm
Key West Islands
Savi Fernandez Band Key West Tour
Thu, 30 Oct at 05:00 pm
Key West
7 Bridges : The Ultimate EAGLES Experience - Key West, FL
Fri, 27 Mar at 08:00 pm
Key West Theater
November's Community Swim
Sat, 15 Nov at 06:00 pm
1319 Duval Street, Key West, FL, United States, Florida 33040
Follow The Rabbit... (6PM)
Sat, 13 Dec at 06:00 pm
Key West Theater
Mac McAnally - Night 2 - SOLD OUT
Fri, 05 Dec at 08:00 pm
512 Eaton St, Key West, FL, United States, Florida 33040
Kaleo Wassman and Friends
Thu, 13 Nov at 07:00 pm
General Horseplay
USD 40
FLO-RAW | Sloppy Joe's Key West
Wed, 03 Dec at 10:00 pm
Sloppy Joe's Bar
KWBW25: Bottoms Up Pool Party
Sat, 01 Nov at 02:00 pm
Island House Key West Gay Hotel & Resort
Scott Kirby- 35 Years of Songs & Stories
Thu, 15 Jan at 07:00 pm
Key West Theater
The Reverend Peyton's Big Damn Band
Sat, 21 Mar at 08:00 pm
Key West Theater
Mac McAnally - Night 3 - SOLD OUT
Sat, 06 Dec at 08:00 pm
512 Eaton St, Key West, FL, United States, Florida 33040
Mac McAnally at Key West Theater
Thu, 04 Dec at 08:00 pm
512 Eaton St, Key West, FL, United States, Florida 33040
Italian Night at the Movies: The Bicycle Thief
Wed, 05 Nov at 05:30 pm
Tropic Cinema
Thomas Dolby at Key West Theater
Fri, 07 Nov at 08:00 pm
Key West Theater
Thanksgiving at Four Marlins
Thu, 27 Nov at 05:30 pm
1435 Simonton St, Key West, FL 33040
Hog’s Boats & Ghosts World Championship Party
Thu, 06 Nov at 07:30 pm
400 Front St, Key West, FL 33040-6617, United States
Anthony Rodia: Laugh Until it Hurts at Key West Theater
Thu, 11 Dec at 08:00 pm
512 Eaton St, Key West, FL, United States, Florida 33040
Swing Dance Night with The Paradise Swing Band at Williams Hall
Tue, 04 Nov at 07:00 pm
729 Fleming Street, Key West, FL, United States, Florida 33040
Scott Kirby- 35 Years of Songs & Stories
Fri, 26 Dec at 07:00 pm
Key West Theater
Tim Palmieri & Friends at The Green Parrot
Fri, 12 Dec at 05:30 pm
The Green Parrot
An Evening Aglow: A Candlelight Christmas with Marjory Lee
Tue, 16 Dec at 06:30 pm
Key West Theatre
DEADFEST KEY WEST - FALL SESSIONS - DEC 5th, 6th & 7th
Fri, 05 Dec at 07:00 pm
The Alamo Key West
Anthony Rodia at Key West Theater
Thu, 11 Dec at 08:00 pm
Key West
Crystal Gayle
Fri, 21 Nov at 07:00 pm
Key West Theater
The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews
Tue, 25 Nov at 08:00 pm
Key West Theater
Italian Night at the Movies: Light in the Piazza
Wed, 03 Dec at 05:30 pm
Tropic Cinema
Holiday Concert at Tennessee Williams Theatre
Sun, 14 Dec at 04:00 pm
Tennessee Williams Theatre
Changes In Latitude at Key West Theater
Tue, 03 Mar at 08:00 pm
512 Eaton St, Key West, FL, United States, Florida 33040
South Florida Symphony Orchestra - Sibelius at Tennessee Williams Theatre
Sat, 24 Jan at 07:30 pm
Tennessee Williams Theatre
FUNDRAISER FOR TOM TAYLOR! Key West musician
Thu, 06 Nov at 02:00 pm
The Alamo Key West
Savannah Brady @ Wellen Park
Thu, 06 Nov at 06:00 pm
Wellen Park Florida
Thomas Dolby
Thu, 06 Nov at 07:00 pm
Key West Theater
Paradise Big Band at Tennessee Williams Theatre
Sun, 25 Jan at 07:30 pm
Tennessee Williams Theatre
December' Community Swim
Sat, 13 Dec at 06:00 pm
1319 Duval Street, Key West, FL, United States, Florida 33040
A Night of OASIS at DURTY HARRY’S
Tue, 27 Jan at 09:00 pm
Durty Harry's
Scott Kirby- 35 Years of Songs & Stories
Thu, 12 Feb at 07:00 pm
Key West Theater
Asleep At The Wheel at Key West Theater
Thu, 15 Jan at 08:00 pm
Key West Theater
Key West Social Clubs 4th annual Pool party and get together
Sat, 08 Nov at 01:00 pm
Key West Social Club
DMTB: The Dave Matthews Tribute Band
Wed, 25 Feb at 08:00 pm
Key West Theater
Phil Collins Experience at Key West Theater
Mon, 26 Jan at 08:00 pm
512 Eaton St, Key West, FL, United States, Florida 33040
Dvořák | Sibelius | Schubert - Key West
Sat, 14 Mar at 07:30 pm
Tennessee Williams Theatre
Rumours ATL: A Fleetwood Mac Tribute
Wed, 21 Jan at 08:00 pm
Key West Theater
Gabriel Rutledge at Key West Theater
Sun, 15 Feb at 08:00 pm
Key West
Scott Kirby- 35 Years of Songs & Stories
Fri, 13 Feb at 07:00 pm
Key West Theater
Yachtley Crew
Wed, 18 Feb at 08:00 pm
Key West Theater
Vienna Boys Choir at Tennessee Williams Theatre
Thu, 05 Feb at 07:30 pm
Tennessee Williams Theatre
The Goodies LIVE at The Alamo for Rock & Boats Weekend
Thu, 06 Nov at 11:00 pm
The Alamo Key West
Los Lobos at Key West Theater
Tue, 13 Jan at 08:00 pm
Key West Theater
The Garcia Project (Jerry Garcia Band Tribute)
Sun, 16 Nov at 01:00 am
Key West Theater
Put-in-Bay Days in Key West 2026
Wed, 11 Feb at 03:00 pm
Key West, Florida
Jimmy Buffet’s The Coral Reefer Band at Coffee Butler Amphitheater
Fri, 16 Jan at 08:00 pm
Coffee Butler Amphitheater
Key’s Collection Racer’s Party (Sunset Greene Lawn)
Tue, 04 Nov at 06:00 pm
3820 N Roosevelt Blvd, Key West, FL 33040-4535, United States
A Date Night Adventure! - The Beauty of Key West
Sat, 02 Nov at 08:00 am
115 Front St
USD 20
Elton Dan and the Rocket Band at Key West Theater
Wed, 12 Nov at 08:00 pm
Key West Theater
The Massacoustics at Key West Theater
Wed, 04 Feb at 08:00 pm
Key West Theater
Elton Dan and the Rocket Band
Thu, 13 Nov at 01:00 am
Key West Theater
Margaritaville at Sea Cruise Ship Special
Mon, 15 Dec at 04:00 pm
Key West Rebecca
Dave Matthews Tribute Band
Tue, 24 Feb at 07:00 pm
Key West Theater
Diva Royale Drag Queen Show Key West, FL - Weekly Drag Queen Shows
Fri, 06 May at 07:00 pm
Diva Royale - Drag Queen Show
USD 25 to 1,100
Kaitlin Butts in Key West
Thu, 29 Jan at 05:00 pm
Truman Waterfront Park Amphitheater
The Expanding Man - Tribute To Steely Dan
Tue, 13 Jan at 07:00 pm
Key West Theater
The Dave Matthews Tribute Band
Tue, 24 Feb at 07:00 pm
Key West Theater
The Coral Reefer Band
Sat, 17 Jan
Coffee Butler Amphitheater
Duval Street Party Presented by Keystar Construction
Fri, 07 Nov at 06:00 pm
Duval St, Key West, FL 33040, United States
Key West Theater | Key West, Florida
Wed, 12 Nov at 08:00 pm
Key West Theater
Early Bird Clean Up United Street and Varela hosted by Children's Montessori School
Fri, 13 Mar at 08:00 am
The Children's School
Anthony Rodia at Key West Theater
Thu, 11 Dec at 08:00 pm
Key West Theater
Southernmost Turkey Trot 5K
Thu, 27 Nov at 08:00 am
The Southernmost Point Buoy
Elton Dan and the Rocket Band
Tue, 11 Nov at 07:00 pm
Key West Theater
Tanner Usrey in Key West
Tue, 27 Jan at 05:00 pm
Truman Waterfront Park Amphitheater
Randy Rogers Band in Key West
Tue, 27 Jan at 05:00 pm
Truman Waterfront Park Amphitheater
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Events in Key West
Entertainment events in Key West