Entertainment events in Key West

Check out happening entertainment events all around Key West, FL

Buffett Through The Years

 Fri, 31 Oct at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Mac McAnally in Key West

 Fri, 05 Dec at 08:00 pm Key West Theater

Peter Antoniou "Psychic" Comedian

 Sat, 11 Oct at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

2025 Fantasy Fest Parade Viewing Party @ First Flight

 Sat, 25 Oct at 06:00 pm First Flight Island Restaurant & Brewery USD 177 to 212

Peter Antoniou at Key West Theater

 Sat, 11 Oct at 08:00 pm Key West Theater

Southernmost Playboy House - Beach Bunny Pool Party Bash

 Fri, 24 Oct at 12:00 pm Southernmost House

Clay Walker @ Country Music Cruise in Key West

 Wed, 29 Oct at 07:00 pm Country Music Cruise

Pajama And Lingerie Party

 Thu, 23 Oct at 10:30 pm Aqua Bar and Nightclub, Duval Street, Key West, FL, USA USD 30 to 115

Dante's 19th Annual Halos & Horns Pool Party

 Thu, 23 Oct at 12:00 pm Dante's Pool Bar & Restaurant

Mac McAnally in Key West

 Sat, 06 Dec at 08:00 pm Key West Theater

Peter Antoniou at Key West Theater

 Sat, 11 Oct at 08:00 pm Key West

Meghan Barter: Human Jukebox Release Concert + Listening Party

 Fri, 10 Oct at 07:00 pm Key West Theater

Lost. Lust. Pixie Dust: A Return To Neverland

 Fri, 17 Oct at 07:00 pm Key West Theater

Tay Tay Tuesday - In Your Wildest Dreams

 Tue, 21 Oct at 06:00 pm Sunset Pier ~ Key West

OCT 11TH

Sat, 11 Oct at 06:00 pm 1908 Flagler Ave., Key West, FL, United States, Florida 33040

Mangoes 2025 Fantasy Fest Parade Party

 Sat, 25 Oct at 06:00 pm Mangoes Restaurant Key West

That Arena Rock Show

 Sat, 18 Oct at 07:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040

Captain Morgan's Masquerade March

 Fri, 24 Oct at 05:30 pm Fleming St, Key West, FL 33040, United States

Crystal Gayle

 Sat, 22 Nov at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Mike Stack and Friends on the BIG stage at the Sunset Pier

 Sat, 11 Oct at 05:30 pm Sunset Pier ~ Key West

Tom Sandoval and The Most Extras

 Wed, 08 Oct at 07:00 pm Key West Theater

KEY WEST, FL - The Marshall Morlock Band @ Hard Rock Key West (Oct. 17th)

 Fri, 17 Oct at 08:00 pm Hard Rock Cafe Key West

Key West Pet Masquerade 2025

Wed, 22 Oct at 05:00 pm Key West Ampitheatre

DEADFEST KEY WEST - FALL SESSIONS - DEC 5th, 6th & 7th

 Fri, 05 Dec at 03:00 pm The Alamo Key West

Mac McAnally in Key West

 Thu, 04 Dec at 08:00 pm Key West Theater

Dave Matthews Tribute Band - BIG Stage / FREE Show

 Fri, 17 Oct at 07:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040

Rock the Tatas 💕

 Thu, 23 Oct at 07:00 pm 409 Caroline St, Key West, FL

25th Annual Living Art Expo

 Fri, 24 Oct at 07:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040

ABC ( Anything But Clothes ) Party

 Wed, 22 Oct at 08:00 pm Halo, the Saint Hotel rooftop lounge USD 30 to 58

Cocktails for Animal Tails

 Tue, 21 Oct at 08:00 pm Rick's Bar

Live Now Love Now Rock and Roll Red Ball Concert for ALS Awareness

Sun, 12 Oct at 07:30 pm Key West Theater

Sloppy Joe's Hangover Headquarters

 Fri, 17 Oct at 10:00 am Sloppy Joe's Bar

Crystal Gayle

 Fri, 21 Nov at 07:00 pm Key West Theater

Buffett Through The Years - Tribute to Jimmy Buffett

 Thu, 30 Oct at 07:00 pm Key West Theater

Hilariously Inappropriate Drag Queen Bingo - A Comedy Show With Balls

 Fri, 10 Oct at 06:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Fantasy Fest Celebration

 Sat, 25 Oct at 12:00 pm 1000 Duval Street, Key West, FL, United States, Florida FL 33040

22&Co Bingo Sundays w/Qmitch - All Candidate

 Sun, 12 Oct at 05:00 pm 22&Co

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

FYT’S 6TH ANNUAL HAUNTED SCAVENGER HUNT

 Sat, 18 Oct at 07:00 pm Curry Mansion Inn USD 27

The 4th Annual “Party Like a Rockstar “

 Wed, 22 Oct at 06:00 pm Kaya Island Eats

Follow The Rabbit... (6PM)

 Sat, 13 Dec at 06:00 pm Key West Theater

Will Kimbrough

 Thu, 30 Oct at 07:00 pm Key West Theater

Peter Antoniou

 Fri, 10 Oct at 07:00 pm Key West Theater

October's Community Swim

 Sat, 11 Oct at 06:00 pm 1319 Duval Street, 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

STORMFRONT ROCKING KEY WEST

 Fri, 10 Oct at 08:00 pm The Alamo Key West

Sloppy Joe's 46th Annual Toga Party

 Thu, 23 Oct at 08:00 pm Sloppy Joe's

The Fabulous Spectrelles

 Fri, 10 Oct at 08:00 pm Kaya Island Eats

Tom Sandoval & The Most Extras

 Thu, 09 Oct at 08:00 pm Key West Theater

KWBW25: Bottoms Up Pool Party

 Sat, 01 Nov at 02:00 pm Island House Key West Gay Hotel & Resort

Wheeland Brothers

 Sat, 08 Nov at 08:00 pm Key West Theater

Thomas Dolby

 Thu, 06 Nov at 07:00 pm Key West Theater

Harry Potter Night of Mischief and Magic

 Fri, 17 Oct at 06:00 pm Sigsbee Community Center

The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers

 Sat, 29 Nov at 08:00 pm Key West Theater

The 4th Annual Official Captain Morgan Pirate Party

 Sat, 25 Oct at 06:30 pm Kaya Island Eats

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

Local Originals at Hank’s

Fri, 10 Oct at 06:00 pm 409 Caroline St, Key West, FL

Follow The Rabbit... (6PM)

 Sat, 01 Nov at 06:00 pm Key West Theater

Custom House Holiday Concert & Bazaar

 Fri, 12 Dec at 05:00 pm Key West Art & Historical Society

The Brit Pack: The Ultimate British Music Experience

Sat, 17 Jan at 08:00 pm Key West Theater

Fantasy Fest 5K Run/Walk

 Mon, 20 Oct at 06:00 pm Duval Street

Mac McAnally at Key West Theater

 Thu, 04 Dec at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Freedom Flotilla Festival

 Fri, 19 Dec at 05:00 pm Key West, Floirda

TuTu Tuesday 2025 - Tuesday Night Fever & Our Robot Friends

 Tue, 21 Oct at 07:00 pm 423 Caroline street, Key West, FL, United States, Florida 33040

On Our Way To Paddy's Day Weekend Celebration!

Thu, 09 Oct at 07:00 pm 528 Front Street, Key West, FL, United States, Florida 33040

LET'S GET LOONEY! FANTASY FEST AFTER PARADE PARTY!

 Sat, 25 Oct at 10:00 pm 420 Appelrouth Lane, Key West, FL, United States, Florida 33040

Scott Kirby- 35 Years of Songs & Stories

Fri, 13 Feb at 07:00 pm Key West Theater

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

Creative Hat Party

 Fri, 17 Oct at 08:00 pm Captain Tony's Saloon "Oldest Bar In Florida"

The Reverend Peyton's Big Damn Band

 Sat, 21 Mar at 08:00 pm Key West Theater

Swayzees Pajama Pool Party

 Wed, 22 Oct at 02:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Southernmost Half Marathon & 10K

 Sun, 12 Oct at 06:00 am Higgs Beach Key West, Florida

Irish Kevin's Annual 80's Party

 Thu, 23 Oct at 10:00 pm Irish Kevins

TUTU Tuesday Pre Party Parade

 Tue, 21 Oct at 05:00 pm Mary Ellen's Bar and Kitchen

Mac McAnally - Night 3 - SOLD OUT

 Sat, 06 Dec at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Dead Doctors & Nurses Haunted Hospital Zombie Watch Party

 Sun, 19 Oct at 06:00 pm 1317 Duval St, Key West, FL 33040-3131, United States

Kash'd Out at Key West Theater

 Fri, 16 Jan at 08:00 pm Key West Theater

Masquerade Monday Wine Dinner Presented by Juggernaut and Bogle Wines

 Mon, 20 Oct at 06:00 pm A&B Lobster House

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

Mermaid Mayhem at the Blue Flamingo Resort

 Sat, 18 Oct at 12:00 pm Blue Flamingo Resort Key West

NightCaps and Nightgowns, a Moon Light Pajama Party

 Sat, 25 Oct at 06:00 pm 319 Duval St, Key West, FL, United States, Florida 33040

Rumours ATL: A Fleetwood Mac Tribute

 Wed, 21 Jan at 08:00 pm Key West Theater

Performing for Key West Wedding

Sat, 29 Nov at 04:00 pm Key West Islands

November's Community Swim

 Sat, 15 Nov at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Bali Bar Party

 Fri, 07 Nov at 08:00 pm 325 Duval St, Key West, FL 33040-6565, United States

PlexXx

 Fri, 24 Oct at 10:00 pm 504 Angela St, Key West, FL 33040-7433, United States

Anthony Rodia at Key West Theater

 Thu, 11 Dec at 08:00 pm Key West

DINNER & A SHOW - TONY BALTIMORE makes you dinner!

 Wed, 26 Nov at 08:00 pm Key West Theater

Mrs. Roper Romp

 Mon, 20 Oct at 05:00 pm Sunset Pier ~ Key West

LUV2GLOW - VIVID DREAMS - FANTASY FEST 2025 @Rick's Key West

 Wed, 22 Oct at 08:00 pm Rick's Bar USD 36 to 117

Mac McAnally - Night 2 - SOLD OUT

 Fri, 05 Dec at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Savannah Brady @ Wellen Park

 Thu, 06 Nov at 06:00 pm Wellen Park Florida

Paparazzi Row Block Party

 Fri, 24 Oct at 04:00 pm 1129 Fleming St, Key West, FL, United States, Florida 33040

Freedom Flotilla Festival

 Fri, 19 Dec at 05:00 pm Key West Free

Ann Hampton Callaway - Finding Beauty: Inspired Classics and Originals

 Mon, 17 Nov at 07:30 pm Tennessee Williams Theatre

Wharfstock at the Schooner Wharf Bar

 Wed, 22 Oct at 07:00 pm Schooner Wharf Bar

Will Kimbrough at Key West Theater

 Fri, 31 Oct at 05:00 pm Key West Theater

Trick or Treat Party at the Farmers Market

 Thu, 30 Oct at 04:00 pm 21 E Quay Rd, Key West, FL, United States, Florida 33040

BARBIE’S PINK POOL PARTY FOR BREAST CANCER AWARENESS

 Fri, 17 Oct at 04:00 pm 200 William St, Key West, FL, United States, Florida 33040

The Hush Hush Theatre + Sushi Productions present... PAST YOUR BEDTIME: A SURREAL EXTRAVAGANZA

 Wed, 22 Oct at 09:00 pm 801 Bourbon bar