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The story of Islander Resort is woven into the fabric of Islamorada. From its early days as an exclusive retreat to its modern reimagining, Islander has evolved with care and intention, honoring its roots while embracing a bright future.

1900s A Pioneering Retreat

The oceanfront land that would become Islander Resort was once home to Henry Flagler’s exclusive fishing camp. Welcoming the Rockefellers and other elite adventurers, it was accessible via Flagler’s railroad, connecting this serene slice of Islamorada to the rest of the world.

1935 Resilience in the Wake of Disaster

The Great Hurricane, a devastating Category 5 storm, reshaped the Keys, leaving a lasting impact on the coastline. Though the original fishing camp was destroyed, the spirit of the site endured. The nearby National Hurricane Monument stands as a tribute to those who lost their lives in the storm.

A Large Sign With A Bridge In The Background

A Vision Realized

1951

Chicago attorney and avid fisherman Leo Samuels established Islander Resort with a dream of creating a tranquil, family-focused escape. Situated along 1,100 feet of coral-sand shoreline, the resort embraced Mid-Century Modern aesthetic, including its now-iconic “Space Age” sign—a bold emblem of 1950s optimism and innovation.

A New Chapter of Preservation

1999

Under new ownership by David Curry, the resort underwent careful renovations that preserved its mid-century charm while introducing eco-conscious updates. Native landscaping, underground utilities, and recycling initiatives ensured that Islander stayed true to its harmony with nature.

A Pool With Lounge Chairs And Umbrellas By It

Embracing the Future

2025

Today, Islander Resort reflects an artful marriage of heritage and renewal. Recent updates honor its history while enhancing the guest experience with modern comforts, sustainable practices, and reimagined amenities. Islander remains a place where generations connect, inspired by the timeless beauty and essence of the Florida Keys.