Key West Holiday 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

Custom House Holiday Concert & Bazaar

Key West Art & Historical Society 12 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

Holiday Lighted Boat Parade

The Perry Hotel & Marina Key West 14 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

Pet Photos with Santa Qlaus and Nick Doll!

Hank's Hair Of The Dog Saloon 13 Dec 2025

Winter Party & Holiday Lights Trolley

May Sands Montessori School 12 Dec 2025

Holiday Bake Sale & Bazaar at Williams Hall

729 Fleming Street, Key West, FL, United States, Florida 33040 13 Dec 2025

An Evening Aglow: A Candlelight Christmas with Marjory Lee

Key West Theatre 16 Dec 2025

🎄🔎 Murder at the Kringels - Murder Mystery

5635 1st ave, Key West, FL, United States, Florida 33040 18 Dec 2025

December Duo Holiday Concert: Irie Monte and Crispin Campbell

533 Eaton St, Key West, FL, United States, Florida 33040 13 Dec 2025

Santa Run + Pilates Wellness Event

Blue Flamingo Resort Key West 13 Dec 2025

Watercolor Fundraiser with Tracey DeLellis at Alonzo's Patio Bar

Alonzo's Patio Bar 15 Dec 2025

Santa Visits the Hemingway Home & Museum! ✨

907 Whitehead Street, Key West, FL, United States, Florida 33040 20 Dec 2025

Curry Ford West's Sleigh The Ford

Curry Ford West 13 Dec 2025

Duo Holiday Concert

The Studios of Key West 12 Dec 2025

Christmas on the Farm Open House

Monroe County Sheriff's Office Animal Farm 14 Dec 2025

Snowy Days Children’s Holiday Concert

5210 College Rd, Key West, FL 14 Dec 2025

New Year's Eve at Four Marlins

1435 Simonton St, Key West, FL 33040 31 Dec 2025

Petal-n-Palette Bubbles & Blooms - Holiday Floral Design Class

The Gardens Hotel Key West Florida 20 Dec 2025

MINGLE & JINGLE at THE SHOPS AT MALLORY

The Shops at Mallory Square 12 Dec 2025

Mingle & Jingle - Holiday Cookie Crawl

The Shops at Mallory Square 12 Dec 2025

Keys Choral Arts: Holiday Concert

Tennessee Williams Theatre 13 Dec 2025

6th Annual Holiday Cookie Throw-Down! You be the judge!

200 William St, Key West, FL, United States, Florida 33040 24 Dec 2025

Christmas Dining at Four Marlins

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

Holiday Yappy Hour at Mac's!

Mac's Place 17 Dec 2025

Holiday Concert at Tennessee Williams Theatre

Tennessee Williams Theatre 14 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

Southernmost Republican Club Holiday Party and Elections

Key West Yacht Club 15 Dec 2025

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

Fausto's Food Palace 12 Dec 2025