The History of Three Waters Resort
The Origins of Holiday Isle in Islamorada
In 1972, Holiday Isle made history when a bartender at the legendary Tiki Bar, known as “Tiki John,” created the very first Rum Runner cocktail. Mixed from a playful combination of leftover bottles of rum and tropical flavors, the drink perfectly captured the free-spirited, colorful personality of the Florida Keys. Word spread quickly, and the Rum Runner became a symbol of island life, drawing visitors from around the world to sip the original in Islamorada.
The Tiki Bar itself grew into one of the most famous beach bars in the world. Its open-air setting, live music, delicious cocktails, and fun energy attracted locals, celebrities, and vacationers alike. Over the years, Holiday Isle became woven into pop culture. The Holiday Isle’s poolside bar was renamed Kokomo, a nod to the Beach Boys’ 1988 hit “Kokomo” that celebrated the easygoing escape of tropical living. In 2013, the Zac Brown Band filmed their music video for “Jump Right In” at the resort, capturing the barefoot, carefree island spirit that Holiday Isle embodied.
From Holiday Isle to Postcard Inn
Through the decades, Holiday Isle continued to expand and evolve, eventually rebranding as the Postcard Inn Beach Resort & Marina. It remained one of the most recognized Islamorada resorts, celebrated for its nightlife, fishing, and beaches. But like much of the Florida Keys, it was tested by storms. Hurricane Irma in 2017 left devastating damage across the property and the island, requiring years of restoration. Still, the essence of Holiday Isle—its people, its music, and its culture—remained unshaken.
Rebirth as Three Waters Resort & Marina
Today, this iconic stretch of shoreline begins a new chapter as Three Waters Resort & Marina, A Tribute Portfolio Resort, named for its unique setting where the Atlantic Ocean, the Gulf of Mexico, and Florida Bay come together. Under the ownership of KSL Capital Partners and management by Davidson Hospitality Group, the property has been reimagined while honoring its roots. Beloved local spots were preserved and renewed Abel’s was carefully relocated to the marina, the Tiki Bar was refreshed while keeping its soul intact, and the Rum Runner once again follows its original recipe. The Kokomo Poolside Bar continues to serve as the perfect place for cocktails, music, and poolside relaxation under the Islamorada sun.
A Florida Keys Resort With a Storied Legacy
Through a partnership with Marriott International, Three Waters Resort & Marina has become the first Tribute Portfolio Resort in Florida, joining a collection of unique, independent hotels celebrated for their authentic character. With modern comforts layered onto its colorful past, Three Waters now offers guests the best of both worlds: an authentic Florida Keys vacation and the elevated experience of a premier Islamorada beachfront resort.
From its roots as Holiday Isle to its evolution into Postcard Inn and now Three Waters Resort & Marina, this property has always been more than just a resort in Islamorada. It is a living legacy—of fishing, music, good times, and community. A place where the past and present meet on the sand. And a destination where every sunrise begins another story in the Florida Keys.
Offers
Make the most of your Three Waters stay with our special offers and exclusive rates.
Three Waters Resort & Marina
Defrost in the Keys
Escape the cold – Book now to receive 25% off and a $150 food & beverage credit. Your sunshine is calling!
Three Waters Resort & Marina
Florida & Georgia Resident Special
Kick back and relax on a tropical beach vacation. We offer Florida and Georgia residents up to 20% off our best available rate.
Three Waters Resort & Marina
Stars, Stripes & Savings
Celebrate America's 250th Birthday. Book now and receive up to 25% off and a $250 dining credit for the 4th of July holiday.
Three Waters Resort & Marina
Resort Hopper: Celebrate Rum in the Keys
Embark on a tropical escape with the Resort Hopper package, featuring a $500 food and drink credit, exclusive rum experiences, and island-hopping via the Rum Runner Water Taxi. Savor signature cocktails, explore three oceanfront resorts, and keepsakes from your unforgettable Florida Keys getaway.
Three Waters Resort & Marina
Members Stay For Breakfast
Enjoy a daily breakfast for two guests at Mercado Morada (50 USD daily value) when you stay with us.
Three Waters Resort & Marina
Helm to Hearth Culinary Celebration (April 17 - 19, 2026)
Secure your spot at the Second Annual Helm to Hearth at Three Waters Resort & Marina — an unforgettable oceanfront weekend celebrating culinary excellence and marine conservation, featuring seven acclaimed chefs.
Three Waters Resort & Marina
Grand Getaway
Escape to paradise with 10% off select oceanview suites. Enjoy island-inspired design and stunning sea views, perfect for a romantic retreat or relaxing getaway. Don’t miss this exclusive offer!
Three Waters Resort & Marina
Resort Retreat Package
Stay 3+ nights and enjoy a $100 nightly food and beverage credit! Indulge in nine culinary destinations—your perfect escape just got better!
Three Waters Resort & Marina
Prepay & Save At Three Waters Resort
Plan ahead for paradise! Book and pay in advance to unlock savings!
Three Waters Resort & Marina
AAA Member Rate
Unlock exclusive AAA member perks and enjoy up to 20% off our Best Available Rate. Simply present your valid AAA membership card at check-in and start saving on your stay.
Frequently Asked Questions
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What is the history of Three Waters Resort?
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What famous bars are located at the resort?
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Is Three Waters Resort the former Postcard Inn Islamorada / Holiday Isle?
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Where was the Rum Runner invented?