Happening Next

Key West Holiday Events

Holiday events Happening Next in Key West, FL

Lobster Trap Tree Lighting

231 Margaret St, Key West, FL, US 25 Nov 2026

Custom House Holiday Concert & Bazaar

 Key West Art & Historical Society 11 Dec 2026
MUSIC

The Lighting of the "Harbor Walk of Lights"

 Conch Republic Seafood Company 25 Nov 2026
HOLIDAY

Wesley House Holiday Village & Bike Ride

 Coffee Butler Amphitheater 4 Dec 2026
CYCLING

Winterfest

 Sigsbee Community Center 3 Dec 2026
MEETUPS

An Evening Aglow: A Candlelight Christmas with Marjory Lee

Key West Theater 15 Dec 2026
MUSIC

December Duo Holiday Concert: Irie Monte and Crispin Campbell

 533 Eaton St, Key West, FL, United States, Florida 33040 12 Dec 2026
ENTERTAINMENT

18th Annual Red Nose Run!

 Southernmost Beach Cafe 12 Dec 2026
SPORTS

Candlelight: Christmas Classics

 Key West Theater 26 Dec 2026
CANDLELIGHT-CONCERTS USD 40 TO 76

Santa at the Key West Cooking Show

 291 Front St suite 207, Key West, FL, United States, Florida 33040 13 Dec 2026
KIDS

Holiday Parade

 Key West Jr Football Field 5 Dec 2026
HOLIDAY

Sip + Shop Key West: Holiday Edition 🌴

 Effortless Creations 12 Nov 2026
KIDS

Nutcracker Key West

 5901 College Road, Key West, FL, United States, Florida 33040 4 Dec 2026
ART

Don't get Scared Now | A Home Alone Event

 Sigsbee Community Center 18 Dec 2026
HOLIDAY

Thanksgiving at Four Marlins

 1435 Simonton St, Key West, FL, US 33040 26 Nov 2026
THANKSGIVING

Santa at the Hemingway gardens

907 Whitehead Street, Key West, FL, United States, Florida 33040 4 Dec 2026
SPORTS

🎅🎄 Suds with Santa at Flagler Wash House! 🫧❤️ Supporting Kids Come First

 1812 Flagler Avenue, Key West, FL 12 Dec 2026
KIDS

Key West Lighted Boat Parade

 0 Duval Street, Key West, FL, United States, Florida 33040 12 Dec 2026
PARADES

Quilting with Margo Ellis: Quilted Gifts for the Holidays

 Williams Hall 24 Nov 2026
WORKSHOPS

ZEN Jewelry Pop-Up Shop at The Perry Hotel Lobby

 7001 Shrimp Road, Key West, FL, United States, Florida 33040 29 Nov 2026

Annual Holiday Ornament Paint Night With Jess

 22&Co Key West 3 Dec 2026
DRAWING-PAINTING

Early Bird Clean Up White Street & Truman Ave hosted by Fausto's Food Palace

Fausto's Food Palace 11 Dec 2026
HOLIDAY

Taz & Jordan's Annual Holiday Party!

925 Seminary St, Key West, FL 33040-4717, United States 13 Dec 2026
PARTIES

New Artworks November Open House: Kick Off to the Holidays

 614 Duval St, Key West, FL, United States, Florida 33040 19 Nov 2026
ART