Key West Christmas Events

Running of the Elves

Key West 20 Dec 2025

Key West Lighted Boat Parade 🎄

631 Greene St, Key West, FL, United States, Florida 33040 13 Dec 2025

A Very Tutu Christmas Trolley 2025!

504 Angela St, Key West, FL, United States, Florida 33040 15 Dec 2025

Holiday Lights Conch Tour Train

Sigsbee Community Center 12 Dec 2025

Freedom Flotilla Festival

Key West, Floirda 19 Dec 2025

17th Annual Rudolph APSMC 5K

Southernmost Beach Resort 13 Dec 2025

Red, lights and GrEEEn Holiday Golf Cart light Tour- The town is LIT!

The Greeen House 17 Dec 2025

An Evening Aglow: A Candlelight Christmas with Marjory Lee

Key West Theatre 16 Dec 2025

Mingle & Jingle - Holiday Cookie Crawl

The Shops at Mallory Square 12 Dec 2025

December' Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 13 Dec 2025

Scrooge Macbeth

319 Duval Street, Rear, 33040 10 Dec 2025

Christmas on the Farm Open House

Monroe County Sheriff's Office Animal Farm 14 Dec 2025

Robert Albury “Key West’s King of Soul” - A Night of Christmas Soul

Williams Hall 11 Dec 2025

A VERY PARROT CHRISTMAS - TONY BALTIMORE & the WILDE AWAKE

Green Parrot Bar Key West 25 Dec 2025

Christmas Dining at Four Marlins

1435 Simonton St, Key West, FL 33040 24 Dec 2025

Key West Christmas Ultimate Adventure H2.O 🎅

631 Greene St, Key West, FL, United States, Florida 33040 25 Dec 2025

Christmas Day Brunch

S/V Argo Navis 25 Dec 2025

Movie Matinee: 'The Santa Clause 2'

Sigsbee Community Center 18 Dec 2025

Christmas Eve & Christmas Day Lunch & Dinner at Yellowfin

5950 Peninsular Avenue, Key West, FL, United States, Florida 33040 24 Dec 2025

Christmas Lunch & Dinner at Matt's Stock Island Kitchen & Bar

7001 Shrimp Road, Key West, FL, United States, Florida 33040 24 Dec 2025

Anthony Rodia at Key West Theater

Key West Theater 11 Dec 2025

Anthony Rodia

Key West Theater 10 Dec 2025