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Holidays at Playa

December Holidays in the Florida Keys

Spend the holiday season at Playa Largo Resort.

Celebrate the season all month long with colorful bayside holiday markets and genuine Caribbean-inspired holiday experiences that bring the best of the season to your getaway at Playa Largo. Join us for weekly holiday fun as you connect with nature and soak up the December sunshine.


December 2, 3, 9, 10, 16, 17, 23, 24 | 11 am - 4 pm

Shop an island-inspired holiday market featuring curated collections of items crafted in the Keys or owned by local vendors each weekend in December.

Featuring Ocean Spa, Sweet Penelope Swimwear, Betty's Pawtique, La Gitana Cafe and Cigars, Keys Koquito, Mermaid and Me, Keys Toys, Cary Castro, Los Cayos Apparel


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Play by the Florida Bay

Holiday Passport to Dine
Dine around the Caribbean and beyond as you set sail through the resort with your own passport to dine. Explore holiday dishes and beverages at each on-site restaurant as you dine around the world to collect stamps and prizes as you explore.
Artisan Holiday Craft Classes
Participate in classes featuring a variety of holiday crafts from ornament making to painting and beyond.

Family Fun in the Island Sun

Tropical Gingerbread Houses

Build and decorate your own island-style gingerbread house.


Holiday Escape Room

Depart on a holiday theme adventure as you're put to the test with our island escape room.


Letters to Santa

Write your letter to Santa then drop it in our magical mailbox


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Christmas Week

Celebrate your holiday island-style December 24 - 25. Indulge in Christmas Eve and Christmas Day dining at Sol by the Sea. Then play by the bay with private water cabanas, rentals from Caribbean Watersports and our Winter Wonderland roller skating rink from December 24 - 31.

New Year's Eve

Cheers to the New Year with a variety of celebrations to choose from.


80s Roller Rink New Year's Eve Party

7 pm - 1 am | Tavernier Ballroom

Take a trip back in time to an iconic era of neon and roller rinks. Zip across our ballroom-turned ultimate 80's hangout with a roller rink, classic arcade games and nostalgic snacks. Big hair and leg warmers welcome.


Havana Nights New Year's Eve Beach Party

6 - 9 pm | Resort Beach

Let the evening transport you to the heart of Havana. Experience the allure of tropical paradise lighted with pops of neon and filled with Cuban-influenced style and flare. Dine and then dance the night away with Latin music under the palms as the colorful sunset appears on the horizon.


New Year's Eve Masquerade at Sunset Terrace

7 pm - 1 am | Sunset Terrace 

Don your mask, then step into an evening of enchantment as you bid goodbye to 2023 and raise a glass to the New Year. Elevated dinner, dessert displays and mixologist-made cocktails will compliment this evening of mystery and fun.





Holidays at Playa Package

Make memories filled with sunshine when you book your Holiday in the Keys package.

  • Collectible Playa Largo ornament
  • Two gingerbread beach cottage kits
  • Up to four tickets to our escape room
  • Daily breakfast for two adults

Use code HOL to book.


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