Two Women Sitting On A Beach
Scroll to Explore

Discover Sunshine and May Celebrations at Islander

Adventures await in the waters and wilderness of Islamorada — the ultimate summer paradise. Shake off the spring showers and bask in our sun-kissed haven with a special lineup of May celebrations at Islander Resort. Whether you want to celebrate Mother’s Day with brunch, kick off summer with a Memorial Day feast, or are seeking to raise a toast on Cinco de Mayo in the Florida Keys, our calendar is packed with play. From craft-making to themed cocktails and beachside BBQs, Islander has a month filled with activities and adventures this May. Join us for a summer escape, where the festivities follow the rhythm of the Keys.

Beach Bliss on Cinco de Mayo 

Start May with a splash at our tropical Cinco de Mayo fiesta. Gather the family for a holiday filled with activities from piñatas on the beach to painting maracas poolside and weaving colorful Ojo de Dios crafts. Then, show off your skills in a sandy soccer match before sampling our delicious lineup of shrimp ceviche, street tacos, and sweet churros. Don’t forget to chill out with a beachside Paloma Spritz or a creamy coconut margarita at Tides — perfect for saying “¡salud!” to the day’s festivities. 

A Memorable Mother’s Day

On May 12, give the moms in your life a day of pampering and play. Start the morning at Elements with our sumptuous Mother’s Day brunch buffet, serving up everything from smoked salmon to farm-fresh eggs and fluffy pancakes. Sweeten the morning with our selection of breakfast pastries and dessert displays. And don’t forget — a special mimosa is waiting for Mom, on the house! 

In the afternoon, spend some together-time with creative on-site activities like our Sip and Paint event, enjoy a thoughtful flower hand-out, wind chime crafts, and Mother’s Day photos. As the sun settles, stop by The Oasis for a cold drink with your toes in the sand. We’re here to ensure every mom sparkles in the spotlight she deserves.

An All-American Memorial Day Weekend 

Nothing kicks off summer like a Florida Keys Memorial Day celebration, and at Islander, we like to celebrate all weekend long. From May 24 to 27, swing by Tides for refreshing drink specials, like our Lynchburg Lemonade. After you’ve spent some time exploring the ocean or tanning beachside, come hungry to our weekend BBQ buffets, featuring staples like burgers, briskets, cold salads, and classic cookout treats.

Throughout the holiday weekend, get in on the action with our Memorial Day activities, like American flag wind chime making, t-shirt tie-dyeing, and t-shirt painting. On May 27, show off your skills at our cornhole tournament, making for a perfect wrap-up to a fun-filled weekend.

Experience More, Save More 

Stretch out your stay and stack up the savings with our Stay More, Save More offer. Stay three nights to save up to 15%, five nights to save up to 20%, or extend your stay up to seven nights or more to save up to 25% off our best available rate. It’s an irresistible excuse to prolong your escape and enjoy every extra moment of island magic. Plus, when there's so much to discover, it’s easy to start living on “island time,” in the essence of the Florida Keys.

This May, book your getaway and let Islander Resort be your playground for fun, serene, and festive vibes. From vibrant Cinco de Mayo festivities to a heartfelt Mother’s Day and action-packed Florida Keys Memorial Day weekend, we’re ready to welcome you to our oceanside oasis. Dive into our calendar to discover all the ways you can celebrate and unwind with us this month, with a splash of Islander charm and sun-kissed joy.

Sign Up for Our Newsletter