• A long shot of the Havana Cabana pool lined with trees and lounge chairs


It’s the most wonderful time of the year! And what better way to celebrate the holiday season than with an island escape to our Key West hotel! With a few weeks left to book our Stay 2+, Save 20% offer, now is the perfect time to treat yourself and your loved ones to a warm island escape! And while you’re here, don’t miss these quirky and festive things to do during an authentic holiday season in Key West.

Party with us at our Havana Cabana’s Elfin Big Holiday Pool Party
Celebrate the holidays with us as we host our final blow out pool party for this year!
The party kicks off in our heated pool at 5PM on December 21st. We will have our very own Floridita Salsa Band playing poolside all night, a live radio broadcast by local party station WEOW 92.7, and an instant photo booth for your selfies with Santa! Dress to impress as an elf or Santa for your chance to win a free night stay! Danny from Rodriguez Cigars will also be there, so make sure to bring a new toy for Toys For Tots to receive your free Rodriguez Cigar!

See the Key West Nutcracker
You may have heard of The Nutcracker, you may have even seen it..but I guarantee you’ve never seen it done in a Key West style! This live performance playing from December 7th- December 16th, has everything from chickens, roosters, sea fans, anemones, and yes, even a conch shell! Set to the enchanting music of Tchaikovsky, the production follows Clara and Fritz as they encounter magical creatures such as the Sea Star Fairy, the Wicked Rooster-King, and many more. This is a great production for both adults and children, and is only shown every 2 years, so make sure to grab your tickets here!

Watch The Lighted Boat Parade
Get in the Holiday Spirit island style, with the Schooner Wharf’s Annual Lighted Boat Parade! The festivities start on December 14th at 6PM with a live musical performance by the children of the House of Pan Steel Drum Band of Bahama Village. The parade then kicks off at 8PM with vessels of all shapes and sizes, dazzled with beautiful holiday lights! Past vessels have included kayaks with battery powered lights, fishing boats, and yachts. The parade takes place at Key West Bight Marina and is free of charge! For more information on the parade, visit the official site here.

See some cute pups at the Key West Dachshund Walk
What’s better than hundreds of dachshunds? Hundreds of dachshunds dressed in cute outfits and costumes of course! Make sure to catch these cute pups at 12PM on December 31st. The parade is free to view, and is also free to enter with no registration required. Over 200 dachshunds and owners participated last year, and even more are predicted to come out this year!

Ring in the new year with Sushi
Ring in the new year in 80-degree weather with Key West’s famous High Heel Shoe Drop! Come out and witness Sushi, our local celebrity/ Queen of Key West as she is lowered down in a giant 6 foot red glittering high heel seconds before midnight! Sushi will be “dropped” from the 2nd story of Bourbon Street Pub on 724 Duval Street right before midnight on December 31st. Make sure to get there a little early though, as thousands of people (including many news outlets such as CNN) will be there to witness the famous drop! For more information, visit the official site here. 

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