Windley Key, Florida
Inns, Lodges, Resorts
December 2025
By Polly Dean
As On The Fly South crew recently headed to the Florida Keys on a fishing trip, we had reservations for the first leg of the trip at Marriott’s Three Waters Resort & Marina in Islamorada. It had been several years since I had been to the Keys, and even though I had been to Islamorada many times, I was not familiar with this resort.
Photo by Polly Dean.
Upon arrival, I was pleasantly surprised and excited to learn that the property was formerly one that I knew very well. For decades, it was known as Holiday Isle Resort. As a youth, college student and young adult, I had spent many memorable (and even not so memorable, thanks to the world-renowned Tiki bar) times there.
Three Waters Resort is named for the meeting of the Atlantic Ocean, Florida Bay, and the Gulf of Mexico. Located on Windley Key in Islamorada, also known as the “Sportfishing Capital of the World,” it’s situated on 15 waterfront acres. The resort blends island adventure with relaxation, taking its inspiration from the tropical beauty and spirit of the Florida Keys.
Photo by Polly Dean.
Stays are available in any of their 214 island-inspired guestrooms, suites or cottages. Many offer balconies, where guests enjoy views of the ocean, marina or lush tropical landscaping. The newly renovated accommodations are designed using inspiration from the island’s flora and fauna. Custom seating, lighting and art are infused into the décor with bold lines and vibrant colors.
Photo by Jimmy Jacobs.
The more popular suites are located in two buildings overlooking the ocean. Some include balconies and floor-to-ceiling windows, or lanais with direct access to the beach, ideal for families or entertaining. Premium accommodations include two “Presidential Suites” providing both a sunrise and sunset view.
Fourteen distinct cottages offer expansive accommodations in a quieter area of the resort. These include an outdoor porch and patio and are perfect for fishing trips or family vacations.
The Cove is an adult-focused oasis with a swimming pool, private beach lagoon, pool-side bar and fitness center. The Cove offers 63 guestrooms and suites, all with king-sized beds and balconies with ocean and beach views.
The family pool. Photo by Jimmy Jacobs.
Nine unique dining experiences are also available on the property. These range from Kindler Wood-Fired Fare that is centered around cooking on an open hearth, Little Limon, a rooftop Latin American dining spot with sweeping views of the ocean, Mercado Morada celebrating the Latin American street market, the Islamorada Pizza Company, pool-side Kokomo and the Cove’s poolside Hideaway. Additionally, there are the Lucky Twist ice-cream window, Starbucks Coffee House, and the Tiki Bar. That latter one was established in 1969 and is the Keys first tiki bar and birthplace of the enduring classic, the Rum Runner cocktail.
The Tiki Bar at Three Water Resort & Marina. Photo by Polly Dean.
The resort and its full-service marina retain much of the same footprint it had in years past. It still holds the same character and amenities as I remember, but even better. Whether you seek world-class fishing, a family vacation, romantic escape, or a dream beach wedding, Three Waters Resort & Marina is your ultimate Florida Keys escape.
I vow to return to Three Waters Resort in the future and I sincerely don’t plan to wait so long between visits. I’ll bet a Rum Runner on that!
