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.
It's the most wonderful time of the year, and we want to help you make this season one to remember. We've got a variety of holiday activities planned for the month of December: caroling, holiday ornament making, letters to santa, hot chocolate bar, wreath making, sandcastle competition... the list goes on! Explore our events to see what else we have in store for you this holiday season!
For Thanksgiving Weekend, why not start your break with something fun? The most lively Thanksgiving Eve party at Tiki Bar is sure to get you in the spirit of things with a festive party and our famous frozen drinks.
Thanksgiving Beach Olympics at Postcard Inn
In our first annual Olympics at Postcard Inn Beach Resort and Marina, you and your partner will gobble your way through yard games, fitness, and obstacle course-like challenges, all leading to the main event, THANKSGIVING DINNER! First prize is a Dinner for Four at Ciao Hound.
Thanksgiving Dinner at Ciao Hound
Join us for Thanksgiving Dinner at Ciao Hound. Enjoy classics like Turkey and Ham with the traditional sides or take your palette on an adventure with grouper puttanesca or lobster ravioli. Bring the family or enjoy a quiet dinner - indoors or on our patio. Dogs are welcome on our Pup Patio.
Thanksgiving Tiki Tailgate
Watch your favorite football team take on their rivals at Postcard Inn's Tiki Bar and Amara Cay's Tiki Bar. Play Football Squares for a cause - $2/square benefits Give Kids the World. Fill in a square and try your luck at both resorts to win prizes.
Escape to the Keys with a relaxing Christmas beach vacation at Amara Cay.
Christmas Eve Carolers
From 12-1pm look out for our festive carolers as you take a stroll in a tropical winter wonderland.
Christmas Day Breakfast with Santa
Keep your eyes open on Christmas morning. Saint Nick will be stopping by each resort to say hello to all of the good boys and girls.
From sand castle building to ornament making, there are endless chances to take advantage of the holiday fun!
Christmas Eve Dinner & Christmas Day Dinner at ReelCatch
Join us this Christmas for a Holiday Dinner at ReelCatch. Enjoy classics like Lamb Chops and Ham or switch it up this year with fresh sea bass or seafood linguini. Bring the family or enjoy a quiet dinner with your spouse. We can't wait to spend the evening with you!
Christmas Eve & Christmas Day Dinner at Ciao Hound
Join us this Christmas for a Holiday Dinner at Ciao Hound. Enjoy classics like Lamb Chops and Ham or switch it up this year with fresh sea bass or seafood linguini. Bring the family or enjoy a quiet dinner with your spouse. We can't wait to spend the evening with you!
Ring in the New Year island-style at Amara Cay.
New Year's Eve Dinner at Reel Catch
Bring on 2023 with a festive dinner at Reel Catch. Enjoy three carefully curated courses with choices of surf & turf, sea bass, and more. Bring the family or enjoy a quiet dinner with your spouse. We can't wait to ring in the New Year with you!
New Year's Eve Party at Raw Bar
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!
Welcome 2023 with sunshine and spirits in Islamorada.
Raw Bar NYE Party Menu
Second Annual Manatee Plunge at Postcard Inn's Beach
Looking to take a dip in the ocean to ring in the New Year? You can on New Year’s Day! Islamorada’s second annual Manatee Plunge at Tiki Bar is hosted in support of Give Kids the World, with the bar opening at 11 am. The Islamorada Manatee Plunge starts at 1 pm. Registration is $10 per person, includes a free beer and proceeds from registration will be donated to Give Kids the World, an 89-acre, nonprofit resort in Central Florida that provides weeklong, cost-free vacations to children with life-threatening illnesses and their families. So, put on a crazy outfit and head to the ocean on Holiday Isle Beach for this fun New Year’s Day event. It’s a refreshing start to 2023.
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.Postcard Inn Resort & Marina Pelican Cove Resort & Marina La Siesta Resort & Villas
“Love, love, love this place. Everything is pretty, well kept and clean. Palm trees by day & fire pit by night plus all the lawn games, pool, & tiki bar. Do yourself a favor & stay.”
“The views are amazing, the pool is tranquil, the beach is spectacular and the rooms are quite nice! Would definitely come back for another stay!”
“Highly recommended this hotel. No need to drive all the way down to Key West. Islamorada has so much to offer. This hotel is a true example of that.”