A serene beach setting with Adirondack chairs around a fire pit, overlooking a calm sea at sunset.

Embrace Holiday Magic at The Islands of Islamorada: A Festive Getaway in the Upper Florida Keys

Published on October 30, 2024

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Dreaming of a holiday escape that combines the warmth of family traditions with a luxurious tropical retreat? The Islands of Islamorada has curated a holiday experience where guests can unwind, make new traditions, and embrace the magic of the season in the heart of the Upper Florida Keys. Here’s a peek into how you can celebrate the holidays in this breathtaking, island paradise.

Your Island Retreat Awaits

Nestled among the turquoise waters and lush landscapes of Islamorada, The Islands is a residential-style resort that offers both spacious one-bedroom suites and expansive four-bedroom waterfront villas. Ideal for families and couples, each villa features a full kitchen, so you can truly feel at home while soaking in the stunning ocean views. Imagine spending your holiday mornings sipping coffee on a private terrace overlooking the sea—no passport required!

Endless Adventures & Island Fun

Whether you’re up for active outdoor fun or a more laid-back beach day, The Islands has something for everyone. You can relax on a private beach, challenge friends on the pickleball courts, or explore the water with paddleboards, kayaks, and fishing gear. To add a special touch to your experience, the resort’s Coastal Concierge team is ready to arrange eco-adventures like snorkeling excursions and interactive marine life tours tailored to guests of all ages.

Festive Island Traditions

Celebrate the holidays with memorable activities that bring everyone together. The Islands of Islamorada invites you to create new traditions in this tropical haven with the following festive options:

  • Christmas Eve Cookie Decorating: Families can enjoy decorating sugar cookies in the comfort of their villa with a holiday cookie kit, priced at $45. Each kit comes with pre-made dough, frosting, and sprinkles to make the sweetest holiday memories.
  • Christmas Day In-Villa Dinner: Skip the holiday cooking stress and indulge in a ready-to-enjoy Christmas feast delivered right to your villa. Choose from classics like turkey, ham, casseroles, and pumpkin pie, with a nod to the local flavor of Florida’s key lime pie. This service makes it easy to celebrate with delicious holiday fare, island-style.
  • Holiday Tree Package: For a touch of holiday spirit, order a beautifully decorated six-foot artificial Christmas tree, set up in your villa for $200. The festive setup includes ornaments and lights, letting you enjoy the season without the hassle.
  • Celebrate New Year’s Eve & Wellness in Style: Ring in the new year with an unforgettable celebration at The Islands! Join fellow guests for a New Year’s Eve party complete with live music from a local artist and a delicious feast. Be sure to reserve your spot in advance to enjoy this lively evening. And to start the year on a high note, The Islands offers a complimentary New Year's Day yoga class followed by refreshing green juices—a perfect wellness reset for 2025.

Special Winter Offers

Whether you're planning a quick trip or a longer winter escape, The Islands offers a few ways to make the most of your stay:

  • Stay Longer and Save: Extend your holiday with discounted rates: save 20% when you stay three nights, 25% for 4-6 nights, or 30% for seven nights or more.
  • Advanced Purchase: For those who like to plan ahead, book your stay at least 14 days in advance to receive a 25% discount on a minimum three-night stay.

View all offers here.

Travel in Style: Seaplane Arrivals

Arrive at The Islands in unforgettable fashion with an exclusive seaplane experience, offered in partnership with Tropic Ocean Airlines. Fly directly to the resort by seaplane and enjoy spectacular aerial views of the Florida Keys on the way—an adventure in itself! The seaplane accommodates up to eight passengers, making it perfect for families or groups looking for a unique travel experience.

Plan Your Holiday Getaway

To ensure your holiday experience is as magical as possible, book your festive arrangements at least two weeks in advance. Ready to celebrate the season in paradise? For more information or to reserve your stay, call (305) 440-3255 or visit theislandsofislamorada.com. Follow along on Instagram @theislandsofislamorada for a daily dose of island inspiration.