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A Guide to the Holidays in Islamorada

The holiday season is a popular time of year for travelers to visit Islamorada and the Florida Keys. This is in part due to the area’s sustained warmth during a time of year when other parts of the country start to feel the winter chill. In addition to our tropical, warm climate, the team at Islander Resort and the community across Islamorada knows how to do the holidays right. 

From special deals to beloved local events, here are some experiences travelers can enjoy in Islamorada this holiday season. 

Enjoy a Tropical Thanksgiving at Bayside Villas by Islander Resort

Thanksgiving is all about family, whether born or chosen, and what better way to treat everyone than with a private villa by the water? For up to six guests, this Tropical Togetherness Thanksgiving Package can provide a dream holiday. The three-night stay spans over the Thanksgiving holiday and includes a three-course Thanksgiving dinner prepared by our Executive Chef at Islander Resort. 

Check Out The 18th Annual Islamorada Holiday Fest | December 2nd

Moving past Thanksgiving, one of the area’s best local holiday traditions returns early this December. The Islamorada Chamber of Commerce Holiday Festival brings over 20 tons of snow to our side of the sunny Florida Keys for some winter magic. There will also be a 35-foot holiday tree blowing snow, a holiday parade, craft booths, and a bazaar with tons of great gift buys. Admission is free. 

The Islamorada Chamber of Commerce Holiday Festival. 87000 Overseas Highway. Islamorada, FL 

Stop By The Fish & Friends Holiday Party | December 13th

In Nearby Key Largo, REEF — the Reef Environmental Education Foundation — will be celebrating the holidays with locals and travelers this December. This monthly meeting typically features workshops and seminars on conservation, but this special holiday installment will instead be a simple party. You can expect tunes, a photo booth, light refreshments, and meet local ocean-life enthusiasts if this sounds fun. 

Fish & Friends Holiday Party. 98300. 8700 Overseas Highway. Key Largo, FL 

Eat at Islander Resort 

For travelers staying in Islamorada throughout the holiday season, one of the best ways to treat yourself is with memorable meals. Those staying at the Islander Resort can take advantage of the property itself being a culinary destination. Seven days a week, you can visit Tides Beachside Bar & Grill and eat from its eclectic, all-day menu. 

For a more upscale holiday meal, guests can also visit Elements Lounge & Restaurant. Reserve a table for Thanksgiving and enjoy a three-course feast at Elements. Other upcoming holiday meals include a Holiday Breakfast Buffet from December 24, 2022 - January 1, 2023 and special dinner menus on Christmas Day and New Year’s Eve.

Book Ahead For Holiday Savings

Book ahead this holiday season and enjoy a discounted rate on your stay at Islander Resort. Take advantage of this Advance Purchase special, which offers up to 15 percent off our best available rate for bookings made 7 days or more prior to arrival.

Spring Sale

Save more when you stay for longer and enjoy savings of up to 25% off

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