It's the most wonderful time of the year! Whether you're celebrating Thanksgiving, Hanukkah, Kwanzaa, Christmas, or New Year's Eve, a trip to the Florida Keys is sure to make your holidays memorable. Skip the planning and let your worries melt away with sunny days on the beach, festive events, daily activities, and delicious meals at our Islamorada restaurants.

DECEMBER 25, 2021


Escape to the Keys with a Christmas beach vacation at Postcard Inn. Gather your loved ones for a beautiful Christmas Brunch at Ciao Hound or indulge in a special Christmas Dinner at Ciao Hound. Celebrate all week long with festive events and activities for guests of all ages.

See all Events

DECEMBER 31, 2021


Ring in the New Year island-style at Postcard Inn. Join us for a Florida Keys New Year's Eve party at Raw Bar complete with tropical cocktails, fresh seafood, and a live band and DJ! For guests seeking an evening dinner of celebration, reserve a table for a prix-fixe four-course New Year's Eve Dinner at Ciao Hound.
Please note: Reservations for NYE Dinner are required with all patrons confirming via a credit card. Please call 301-905-8392 for reservations and questions.  

Oceanfront restaurant in Islamorada at Postcard Inn

JANUARY 1, 2022


Welcome 2022 with a New Years Brunch at Ciao Hound. Featuring favorites such as Banana Bread French Toast and Short Rib Hash, as well as morning cocktails and treats for all, guests can kick their new year off right with sunshine and spirits in Islamorada. 

FEBRUARY 14, 2022


Join us for an elegant evening dinner for you and your loved one at Ciao Hound in islamorada. Our Valentine's Day Dinner features a four-course prix-fixe menu with choices ranging from Lobster Ravioli to Grouper Puttanesca and Molten Lava Chocolate Cake. 

Friends on a Florida Keys vacation dining by the ocean



Guests enjoy complimentary shuttle service from 3 pm - 11 pm every day to our other resorts and local attractions between MM 77.5 to MM 85. The Front Desk can arrange your shuttle service or provide the direct phone number to request a pick-up during your stay.

stay & explore all 4

When you stay at one of the resorts in the Islamorada Resort Collection, you'll have access to explore the unique amenities, events, and restaurants of four resorts. Guests enjoy free shuttle service between each resort as well as nearby attractions.

Amara Cay Resort  Pelican Cove Resort & Marina  La Siesta Resort & Villas


Guests playing games by the beach

Up to 40% Off

Take a vacation from inflation. Book at any Islamorada Resort Collection destination and receive up to 40% off. Hurry! Limited time sale.

Book Now