Make It a May to Remember at Grassy Flats

From Mother’s Day pampering to Memorial Day sunsets, May is the perfect month to escape to the sun-soaked serenity of Grassy Flats Resort. Whether you're craving adventure, relaxation, or one last rooftop toast before summer, there’s something special happening all month long. Here’s why May is the perfect time to book your tropical getaway.

Treat Mom to Paradise – Mother’s Day Brunch at the Rhum House (May 11)

This Mother’s Day, trade flowers and cards for sunshine, fresh flavors, and time well spent. Join us at The Rhum House for a laid-back yet elegant brunch designed to pamper Mom with island-inspired dishes, tropical sips, and warm ocean breezes.

Make your reservations here.

Key West Paddle Classic (May 10)

We're proud to host fans and participants of the legendary Key West Paddle Classic. Whether you're racing, cheering from the shoreline, or just soaking in the energy, Grassy Flats is the perfect home base.

Check out their silent auction here!

Last Call for Rooftop Views – Palm Deck Closing for Summer Soon

This is your final chance to catch a Grassy Flats sunset from the Palm Deck rooftop before it closes for the summer! Through Memorial Day, we’re serving up breezy cocktails, live music, and the kind of golden-hour views that stay with you long after vacation ends.

Come raise a glass and take in one more sunset before the Palm Deck’s summer break!

Memorial Day Weekend – Summer Starts Here (May 24–27)

Looking for a quiet yet unforgettable way to kick off summer? Memorial Day Weekend at Grassy Flats is your answer. Think warm days on the water, cool nights under the stars, and plenty of space to relax, reflect, and reconnect.

Whether it’s a couples' escape, a family trip, or a last-minute getaway with friends, our beachfront setting and low-key vibes make for a perfect long weekend.

Expect a few special touches that weekend, including live music, fresh local bites, and everything you need to welcome summer the right way.

May Is Magic — Come Feel It for Yourself

May is the perfect time to experience the magic of Grassy Flats. From honoring the moms in your life and cheering on paddle boarders, to rooftop sunsets and Memorial Day memories, this month has it all.

Don’t wait — rooms are going fast! Book your stay today and let the countdown to your island escape begin.