Ensconce yourself within the ocean-inspired design of our rooms while looking out over the harbor and pools from your private balcony.
As the winter holidays approach, Key West embraces the festive season in its own unique way. For our cherished guests and anyone eager to experience the holidays with us, this guide shines a light on the must-see events and celebrations that make our island a winter wonderland unlike any other, all just steps away from our Key West Harbor resort. Where else but Key West can you trade snowflakes for palm trees and still feel the magic of the holidays sprinkled with that island flair? Explore the season's premier happenings and discover the festive charm and island flair that only Key West can offer
Our holiday season kicks into full swing with the 2023 "Harbor Walk of Lights" lighting up on November 22nd. A mere stone's throw from our Key West Harbor resort, the Harbor Walk at Greene and Elizabeth St. turns into a sparkling display of maritime magic. We're talking about the standout 20-foot Fishing Buoy Tree, the 16-foot Nautical Christmas Tree, and our all-time favorite, the Lobster Trap Tree. All of this beautifully captures the Key West vibe. Don't miss out on those fun light sculptures think playful pelicans, manatees, and yep, our iconic pink flamingos all shining bright under palm trees. Lazy Way Lane is also getting into the holiday spirit, so don't forget to check it out!
The 3rd annual Holiday Village & BeLighted Bike Ride is here, and it promises to be more enchanting than ever. Touted as the ultimate kick-off to the festive season in Key West, the Holiday Village offers an exhilarating evening for folks of all ages. This year, we're upping the ante with not one but two exciting rides. And for our younger guests? They can look forward to two expansive, holiday-themed inflatable obstacle courses. And because it's Key West and we love a touch of the unexpected, don't be too surprised if you see a hint of snowfall! The BeLighted Bike Ride, a radiant spectacle on wheels, takes off at 8 p.m. from the Truman Coffee Butler Amphitheater. Cyclists will trace the iconic route of the Fantasy Fest Parade. And for those who've decked out their bikes? Stay on after the ride for the "best bike" contest. It's time to light up the night! Holiday Village 4-8 pm. The bike ride leaves at 8 p.m. (Photo courtesy of Carol Tedesco.) Learn more.
Imagine the picturesque streets of Key West bursting with energy as local bands, community floats, and spirited groups participate in the Hometown Holiday Parade. The parade begins at 7 p.m. at Truman Avenue and White Street, right next to Bayview Park, and then winds its way down Duval Street before concluding at Eaton Street. The highlight for many? Seeing the children's faces illuminated with joy and anticipation at the magical sight of Santa. Truly, it's one of our most cherished holiday parades.
Next up is the Key West Art & Historical Society's Holiday Concert & Bazaar at the Key West Museum of Art and History, also known as the Custom House (the Big Red Brick Building.) This evening presents a joyous ensemble of local artisans, melodic choirs, and holiday entertainment, complemented by a sprinkle of festive libations. And let's not overlook the mesmerizing light show, thoughtfully designed by the brilliant minds at Key West High School's Conch 5 Studios
All aboard the Conch Tour Train for a delightful tour of Key West's holiday-decked spots. It's an hour tour that takes you to all of the island's most elaborately decorated neighborhoods, and there will be caroling too. Tickets are priced at $32.95 for adults and $22.95 for kids, with tots under two riding for free. Don't miss the special holiday glasses that add an extra sprinkle of magic to the already enchanting sights! For ticket information, click here.
Key West brings its unique flair to the festive season with the 32nd Annual Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade on December 9th. As the sun sets and 8:00 pm approaches, the Key West Bight and Harbor become a dazzling display of maritime merriment. The festivities commence at 6 pm, with the Harbor Walk coming alive with twinkling decorations and the infectious melodies of Caribbean Christmas carols, thanks to the Bahama Village Music Program's "House of Pan" steel band.
A variety of vessels, from battery-lit kayaks to grand schooners, showcase the island's creativity, adorned with everything from playful dolphins to iconic conch shells. It's not just a parade; it's Key West's maritime holiday tradition, reflecting the island's spirit and charm. With palm trees as festive symbols, dancing gingerbread men, and a hint of the Grinch, this event celebrates the season in true Conch Republic style. (Photo courtesy of Carol Tedesco.)
New this year! At Truman Waterfront Park, the Coffee Butler Amphitheater is transforming into a wintry oasis this December. Even amidst Key West's tropical climate, we're introducing a sprinkle of winter magic. Guests can glide on a custom ice skating rink, complemented by festive music and twinkling lights. Winter Wonderland also features rides like carousels and slides, a vendor village for unique holiday shopping, and a variety of tasty treats. For the little ones, there are crafts, letter-writing to Santa, and memorable photo opportunities.
Admission is just $10 per person, with children 5 and under entering for free. An additional $20 lets you skate for an hour, and a $10 All-You-Can-Ride wristband provides access to all the rides. For ticket information, click here.
We end the year with not one, but three sensational drops! Whether it's the new Queen's "Red Shoe Drop" at the Bourbon St. Pub, the iconic "Dropping of the Conch Shell" outside Sloppy Joe's Bar, or the thrilling "Lowering of the Pirate Wench" at Schooner Wharf Bar in the Historic Seaport, there's a countdown for everyone. (Photo courtesy of Rob O'Neal.)
Where palm trees twinkle and waves gently sway, Key West holidays light up in the most tropical way! Ho Ho Ho and Happy Holidays from our family to yours! #lovethemarker
October 17, 2025
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Waterfront Luxury
Ensconce yourself within the ocean-inspired design of our rooms while looking out over the harbor and pools from your private balcony.
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