9 Christmas Events in Key West (2025)
As any regular visitor can tell you, Key West, aka the Conch Republic, is a truly unique and special destination any day of the year. You might think of us as a beach and watersports destination where you can swim, jet ski, and go snorkeling to your heart’s content. However, the winter season and the Christmas holidays are when the magic really happens.
If you are staying at one of our premier vacation rental properties during this special holiday, you’ll become aware of a sort of paradox going on in Key West. While our locals and visitors can most definitely go over the top with decorations, events, costumes, and so forth, the tempo is somehow less frantic than in other parts of America.
Maybe that’s because we are a small, friendly Florida Keys town, or maybe it’s the swaying palm trees and sunny weather — the December averages for Florida are a comfortable 77°F in the daytime and 70°F at night.
Let’s explore the most festive holiday events to experience during your magical Key West Christmas.
1. Key West Harbor Walk of Lights
Date: November 26th – December 31st
Head down to the Key West Historic Seaport (home to the famous Key West Bight Marina) for the Key West Harbor Walk of Lights and stroll through three blocks of dazzling light displays, Christmas trees, holiday music, and special appearances by Santa and Mrs. Claus.
The lights stay on every night from Thanksgiving through New Year’s Eve, making it the perfect family-friendly holiday outing throughout the holidays.
2. Holiday Village & BeLighted Bike Ride
Date: December 5th; 5-9 pm
A (sort of) parade of a completely different stripe is the Holiday Village & BeLighted Bike Ride, a benefit for Wesley House Family Services. Staged at the Coffee Butler Amphitheater in the beautiful Truman Waterfront Park, this family-oriented gathering is full of holiday cheer and culminates in a lighted bicycle ride.
Take this opportunity to see Key Westers apply their creativity and holiday spirit to their beloved bicycles, all while helping a worthy local organization, and stroll the Holiday Village full of fun festivities for all ages.
3. Hometown Holiday Parade
Date: December 6th; 7-10 pm
Barely one month after the madness and excess of the Fantasy Fest parade, this small-town confection will warm your heart and put you in the mood for the month ahead. The floats have a very homemade feel, and most of the marching groups are not bands.
Expect to see a few pirates and “parrot heads” sprinkled into the mix, because, hey, it’s Key West. But the Hometown Holiday Parade is a family-friendly event. The kids are delighted to scramble for the candies being tossed their way and interact with the parade participants. No crushing crowds are lining the parade route, and there is room for everyone to spread out and enjoy the great holiday vibes as the procession moves down Truman Avenue and then up Duval Street to Eaton Street.
4. Eaton Street Christmas Stroll
Date: December 7th; 3:30-7pm
One great way to start seeing the trimmings and get into the holiday mood is by joining in theEaton Street Christmas Stroll. This annual free event allows you to wander down historic Eaton Street while taking in the sights and meeting new friends.
Stop at various venues along the route offering music, entertainment, snacks, and maybe even a cocktail or two. You might even catch a special performance by the Keys Choral Arts community chorus caroling along the way for an extra dose of festive fun!
5. Conch Train Holiday Lights Tour
Date: December 8th and December 11th – 23rd; every 30 minutes from 6-8:30 pm. If you just want to cruise around enjoying the holiday sights, walking or bicycling around Old Town in our glorious subtropical climate should be perfect for you. But the extra festive option is to take the Key West Holiday Lights Train Tour.
Around the holidays, the famous Key West Conch Train offers special tours to see all the best holiday lights on the island, it’s a can’t miss! You’ll also find similar holiday light tours available through Old Town Trolley Tours.
6. The Rudolph Red Nose 5K Run
Date and time: December 13th; 8 am
Get ready to “run run Rudolph” Key West style at the annual Rudolph Red Nose 5K. It’s a serious race that doesn’t take itself too seriously — and it benefits a worthy cause! Santa hats and reindeer antlers abound, and, of course, red noses. But the real kicker is that everyone shows up in their finest Christmas pajamas!
This run benefits Positive Step of Monroe County, a 501(c)(3) non-profit organization serving Monroe County’s highest–risk kids and their families, and runners and walkers of all ages and abilities are welcome to participate.
The festivities extend throughout the day, with pool parties, a “Merry Market,” and a Christmas Pageant.
7. Schooner Wharf Lighted Boat Parade
Date and time: December 13th; Parade at 8 pm but expect other entertainment starting at 6 pm
Just a few days after the street parade comes the annual Lighted Boat Parade at the Key West Historic Seaport. Fishing boats, sailing ships, yachts, catamarans, and dinghies cruise by, each festooned with Christmas lights and decorations ranging from silly to spectacular.
Spectators line the harbor and fill up Schooner Wharf bars and restaurants to catch a glimpse of the light displays, and a party ensues, which lasts all evening and well into the wee hours.
Tip: The entire Key West Harbor Walk and Key West Bight Marina are decorated and lit up for the holidays, so while you’re here for the light show, you can enjoy a stroll to take in the sights and immerse yourself in the celebration.
8. Holiday Historic Inn Tour
Date and time: December 12th and 19th; 6-8 pm
For a curated tour that is an evening’s entertainment in itself, the Holiday Historic Inn Tour may be for you. Both dates take you to different destinations so if you’re in town on both dates, you won’t get a repeat performance. Each destination is decked out in its holiday attire, and at each stop, your hosts will give you a tour of the property, offering you holiday treats along the way.Tip: As you are checking out the various displays around the island, be sure to stop by Bayview Park to see the Official Christmas Tree and Menorah of the City of Key West. The tree is illuminated for the entire month, and a ceremonial lighting of the menorah takes place on the first evening of Hanukkah.
9. Christmas Day on Duval Street
Date and time: December 25th, all dayOne of our favorite things to do on Christmas Day is to head for Duval Street to enjoy the all-day promenade of strolling visitors and locals in their finest (or wackiest) holiday attire. Many of the restaurants, bistros, and cafes along this main drag offer outdoor seating on decks, porches, or balconies overlooking the sidewalk parade out front, so this is a perfect way to enjoy brunch or dinner.
If you are a visitor to the island, we suggest scouting out your perfect spot earlier in the week and making a reservation to ensure you nab the best seats for your special day.
A Festive Winter Wonderland in Key West
If you’re dreaming of a warm-weather Christmas filled with lights, tropical breezes, and island charm, Key West is the perfect place to celebrate—and the best way to experience it is with a stay that feels like home.
VHKW offers a curated collection of private vacation rentals, from historic Conch homes with wraparound porches to luxurious ocean-view villas, cozy cottages, family-friendly houses with pools, and elegant estates steps from Duval Street. Whether you’re planning a romantic holiday escape, a laid-back family gathering, or a festive getaway with friends, you’ll find a space that fits your style and puts you right in the heart of the island’s holiday magic.
Ready to unwrap your Key West Christmas? Book your holiday stay with VHKW.
