When most of the U.S. bundles up against winter, a warmer celebration waits down South. Spending the holidays in Key West, Florida, means trading bulky jackets for sandals and gray skies for sunshine. The island’s easygoing charm takes on a festive glow, with twinkling lights woven through palm trees and Santa arriving by boat instead of sleigh.
If you are dreaming of a warm place to celebrate the holidays in style, few destinations make it feel as special as Key West. Compass Realty is here to tell you what makes the island such a wonderful place to celebrate.
Embrace Island Warmth
While family up North scrapes ice off the windshield, you could be walking the beach in shorts. Key West stays mild and sunny through late fall and winter, with daytime highs usually in the mid-70s to low 80s and comfortable evenings. That warmth makes November and December ideal for biking through Old Town, dining outdoors, and catching the sunset from the water. For many travelers, the weather alone is reason enough to head South for the season.
Thanksgiving in Paradise
The holidays in Key West, Florida, kick off with a tropical take on Thanksgiving. Start the day at the Southernmost Turkey Trot & Rooster Romp, two festive running events from the Southernmost Point Buoy that support local reef conservation.
When it is time to eat, restaurants across the island serve traditional turkey dinners alongside Key West favorites like fresh seafood and Key lime pie. If you want to prepare your own Thanksgiving dinner, Compass Realty’s Key West vacation rentals have kitchens, allowing you to prepare the perfect holiday meal. Late November also brings the Lighting of the Bight at the Historic Seaport, which officially switches on the island’s holiday lights.
Festive Things to Do During the Holidays in Key West, Florida
As December arrives, the island really knows how to celebrate. The Key West Historic Seaport glows nightly with the Harbor Walk of Lights, three blocks of glittering trees, holiday music, and colorful displays. Santa swaps his sleigh for a sailboat during the beloved Schooner Wharf Lighted Boat Parade, when a fleet of decorated vessels drifts through the harbor after dark.
Beyond the waterfront, the calendar stays full:
- Watch the Hometown Holiday Parade wind through Old Town with floats, music, and local charm.
- Take a holiday lights tour to see historic homes decked out in elaborate displays.
- Set sail on a Cocoa and Carols cruise for hot cocoa and Christmas songs on the harbor.
- Ring in the new year with Key West’s famous midnight “drops,” the island’s quirky answer to the Times Square ball.
You can plan around even more seasonal fun with the island’s holiday event calendar.
Where to Stay for the Holidays
Making the most of the holiday season means having a comfortable place to call home after a day of celebration and cheer. At Compass Realty, we offer vacation rentals throughout Key West, including in Old Town, Truman Annex, and more. Instead of squeezing into a cramped hotel room, your whole group can spread out in a private home with full kitchens, multiple bedrooms, and inviting living spaces. Cook a Thanksgiving or holiday feast, gather around the table, and celebrate together in true island style.
Browse our full collection of rentals to find the perfect spot for your getaway. Reserve your stay online or call us at 305-292-1881 to start planning your escape.
