Celebrate the Holidays in Paradise
Whether you’re traveling from the Northeast or driving down from northern Florida, winter feels entirely different in Islamorada. Instead of icy mornings, you’ll find ocean breezes and warm evenings illuminated by twinkle lights. December at Islander Resort is crafted for travelers seeking sunshine, celebration, and a touch of the unexpected — all wrapped in the laid-back charm of the Florida Keys.
This season, Islander Resort invites guests to experience the holidays through its Seasons of Sunshine program — a collection of festive events and special moments that make December one of the most memorable times of the year in Islamorada.
At the heart of the festivities is Sandy’s Bar, where each Friday transforms into a cheerful escape during the Sandy Claus Social. Guests can sip seasonal cocktails, enjoy live music, and join in lighthearted activities like the Elf Name Cocktail Contest or Sparkle Up Sandy’s craft hour to create keepsake ornaments or seaside postcards. The highlight of the month, the Big Sandy Claus Soirée on December 26, brings everyone together for live entertainment, trivia, and festive surprises — a perfect way to close out the year island-style.
For something more intimate, Snow Globe by the Sea offers an unforgettable beachfront dining experience. Drift restaurant hosts private igloo dinners under the stars, complete with a curated three-course menu and chilled champagne, creating a one-of-a-kind evening framed by the sound of the waves and the glow of the Atlantic horizon.
Families and couples alike can fill their stay with resort-wide activities featured on the Resort Happenings Calendar — from relaxed Yoga by the Sea sessions to live entertainment and beachside gatherings. Each event captures the genuine, easygoing atmosphere that defines Islander Resort and the spirit of the Florida Keys.
Beyond the resort, the village of Islamorada offers even more reasons to explore. Local galleries and shops feature coastal gifts and handmade art, while nearby events like the Morada Way Art Walk and waterfront dining experiences extend the festive feeling throughout the island. It’s the perfect pairing of laid-back island life and seasonal excitement.
Guests staying at either Islander Resort or Bayside Villas will find comfort, space, and connection at every turn. Oceanside rooms and multi-bedroom villas make it easy to relax between adventures, while direct beach access and resort amenities keep the focus on enjoying the moment — not the weather back home.
This December, trade the snow for sunshine, the scarves for sandals, and discover why the Florida Keys are the perfect setting for your holiday escape.
Plan your Seasons of Sunshine getaway at Islander Resort or Bayside Villas — where every day feels like a celebration, and the season shines a little brighter by the sea.