Dreaming of a Christmas without shoveling snow, scraping windshields, or wearing six layers just to grab the mail? Welcome to Christmas in the Florida Keys, where the palm trees sparkle, the sunsets show off, and Santa may arrive by boat instead of sleigh. 🎅🌴

The Keys don’t do ordinary holidays—we do them island-style. Here’s what makes Christmas week down here so special (and why smart travelers start booking early 👀).

🎅 Boat Parades & Harbor Lights & Conch Tour Trains

Christmas boat parades are a BIG deal in the Keys. Locals deck out their boats with lights, inflatable Santas, and full-on island flair, then cruise through the harbors after dark. It’s festive, quirky, and very “only in the Keys.” Bring a cocktail, grab a dockside seat, and enjoy the show.

Hop on the Conch Tour Train and go caroling through the streets of Key West to see all of the lights and decorations on our tiny little island.

🎶 Live Music, Everywhere

From laid-back acoustic sets to full bands playing holiday tunes with a tropical twist, live music is part of the daily rhythm here. Bars, marinas, restaurants—you’ll hear everything from Jimmy Buffett vibes to reggae-Christmas mashups you didn’t know you needed.

🎁 Holiday Shopping (Keys-Style)

Skip the mall madness. Christmas shopping in the Keys means art walks, pop-up markets, handmade gifts, coastal décor, and one-of-a-kind finds. You’ll leave with gifts that actually have stories attached—and probably a little something for yourself (because island rules).

🏖️ Beach Days in December (Yes, Really)

While the rest of the country is bundled up, we’re enjoying sunshine, gentle breezes, and temps that scream flip-flops encouraged. Christmas Day might include a morning walk on the beach, afternoon boating, and sunset cocktails. Ugly sweaters optional.

🍽️ Festive Dining Without the Stress

Many local restaurants serve special holiday menus—fresh seafood, tropical sides, and seasonal cocktails—so you can enjoy Christmas dinner without cooking for a crowd. Or cook at your rental and eat outside. Because… December al fresco dining? Yes please.

🎄 A Holiday That Feels Like a Vacation

That’s the real magic of Christmas in the Florida Keys. It still feels festive—but also relaxed. No rushing. No freezing. Just sunshine, salt air, and time well spent with the people you love. You will find me out in the kayak paddling around the bay on Christmas day. As a bonus our sunsets and sunrises are truly amazing this time of the year.

🏃‍♀️ Holiday 5Ks & Festive Fitness Fun

If your idea of holiday cheer includes sneakers, a little sparkle, and earning that extra slice of pie, the Florida Keys deliver in a big way.

Throughout December, you’ll find festive 5Ks and fun runs like Running with the Elves, holiday charity races, and themed runs where costumes are encouraged (elf hats, ugly sweaters, tutus—no judgment, only applause). These events draw locals and visitors alike and are all about fun over finish times… though the scenery alone might make you PR without trying.

Picture this:
✔ Running at sunrise with palm trees instead of pine trees
✔ Holiday music playing instead of sleigh bells
✔ Post-race snacks enjoyed in shorts, not parkas

Many of these races support local charities and community organizations, so you’re burning calories and doing good. Whether you’re a seasoned runner, a casual jogger, or a “walk-it-for-the-t-shirt” participant, there’s a spot for you on the starting line.

And yes—spectators are welcome, especially the kind holding coffee or mimosas at the finish line. ☕🥂

📅 Thinking About Christmas Next Year? Start Now.

Holiday and winter-season vacation rentals book FAST in the Florida Keys. Click here to browse our rentals.

Prime properties—especially waterfront homes, pool homes, and larger family-friendly rentals—are often reserved months (sometimes a year) in advance. If Christmas 2026 (or winter season in general) is on your wish list, now is absolutely the time to start planning.

Early booking =
✔ Best selection
✔ Better locations
✔ Less stress
✔ More margaritas later 🍹

🎁 Ready to Put a Little Paradise Under the Tree?

Whether you’re dreaming of a cozy canal-front retreat, a boating-friendly home, or a place where Christmas morning includes palm trees and sunshine, I can help you find the perfect Keys escape.

Because Christmas memories hit different when they’re made in paradise. 🌴✨

And trust me—you don’t want to be the one saying, “We should’ve booked sooner.”

See you next Christmas