Courtesy Three Waters Resort & Marina
It’s hard to beat a sunrise over the ocean, and at Three Waters Resort and Marina, they are truly a spectacle. The sprawling oceanfront property sits in Islamorada, a quiet Florida Keys community whose moniker translates to “purple island” in Spanish (likely due to those glorious morning displays). The resort itself derives its name from the convergence of the Florida Bay, the Gulf of Mexico, and the Atlantic Ocean; it’s no surprise then that water-based fun is the focus of this 15-acre slice of paradise.
Courtesy Three Waters Resort & Marina
The 214-key, dog-friendly property features a range of accommodation styles, from rooms just steps away from the sand to cottages fit for the whole family to the newest addition: the Cove, an adults-only hideaway secluded from all the resort goings-on—of which there are many. Dine at seven eateries, including a splurge-worthy new steakhouse, an open-air Latin American–influenced breakfast spot, and the Tiki Bar, home of the very first Rum Runner.
Courtesy Three Waters Resort & Marina
There are three pools—including the only swim-up bar in the Keys—and plenty of activities scattered around the property, from bocce ball to an arcade. Kayaks, paddleboards, two-person catamarans, and jet skis are available to take out for the day. And don’t forget add-on experiences like seaside massages and private fishing lessons (Islamorada is the Sportfishing Capital of the World, after all). Read: You will not get bored. And yet, there’s a case to be made for simply taking it easy. So order that Rum Runner, settle into a lounge chair under a shaded cabana, and relax.
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INSIDER INTEL
Stacey Peringer, director of guest experiences, shares her Islamorada musts
SECRET GARDEN
“My favorite way to spend a Sunday morning after a workout is hitting up Cafe Moka Islamorada. I love grabbing an iced coffee and soaking up some peace on their garden patio.”
GIFTING GO-TO
“Anytime someone asks me where to find unique home decor or gifts, I recommend Sea Dragon. All my favorite carved wood furnishings, lamps, and art pieces in my home have come from there.”
SECRET SAUCE
“One place I’m always down for is Islamorada Brewery & Distillery. It’s super ‘Keys-y,’ and most everything on the menu is brewed right there. The Lavender Lemonade is my current cocktail obsession.”
This article appears in the Spring 2026 issue of Southbound.
