In the 18th century, before America’s independence from England, Bahamian vessels frequented the waters surrounding what we know today as the Florida Keys. In the crystal-clear waters behind Turtle Key (today, part of Islamorada, the Village of Islands), Bahamian sailors hunted for turtles (indigenous and common) and occasionally shipwrecks.

In the summer of 1723, such sailors had been hunting turtles when they came across a large Spanish galleon sinking on the notorious Alligator Reef just south of Turtle Key. These salvagers didn’t even wait for the ship to settle before boarding and plundering the ship.

Loaded with booty, they needed a place to hide it. Their own boat was too small to carry the treasure so many sailors captured giant Leatherback Sea Turtles, each weighing 2,000 pounds, and rode them to shore. Via what we now know as Turtle Key Channel, the pirates made shore with their booty and proceeded to bury it.

By 1730, the Bahamian pirates disappeared from the Turtle Key area. It was rumored that they were forced to return home for political reasons, leaving much treasure behind. Although many have searched, that treasure from 1723 has never been found. By 1760, even Keys natives were nowhere to be found, as many were taken as prisoners by other invaders.

Due to migration surrounding the Revolutionary, Seminole and Civil Wars, Islamorada grew in the 18th and 19th centuries. In addition to pirates and salvagers, pineapple and turtle farming became common.

In the 20th century, the miracle of Flagler’s Folly, aka the Florida East Coast Railroad, changed life forever in the Keys. For a time, the railroad ended at the edge of Turtle Key. Tragically, in 1935, disaster struck Turtle Key: a category 5 hurricane devastated the Middle Keys, with the eye passing directly over Turtle Key.

Hundreds were killed and a monument to this no-name storm remains in downtown Islamorada. Flagler’s railroad was destroyed, many lost their homes and the economy, already suffering from the Great Depression, collapsed.

After the hurricane struck, the Red Cross Foundation built 19 Red Cross homes in Islamorada, including one on Turtle Key. These homes were virtually indestructible, likely even more storm resistant than the best homes today built to modern storm building codes! The Red Cross home remaining today on Turtle Key is known as the Hawksbill Cottage, named for a sea turtle species commonly found in the area.

It took a generation for Turtle Key and the surrounding area to recover from the great storm of 1935. Over the years, the Red Cross Cottage (Hawksbill Cottage) saw many uses, including a brothel and a waypoint for a thriving rum-running business, both benefiting from Turtle Key Channel and the deep, blue waters in front of Turtle Key.

Today, Turtle Key has lost some of these colorful activities, but remains a hub of island living and host to new beginnings – weddings – almost every weekend! More broadly, Islamorada is a thriving destination in the Florida Keys known for snorkeling, SCUBA, fishing and boating.

*Based on truth but touched by love and inspiration from the Florida Keys!

Property Overview

Situated on roughly four acres of beautiful secluded island, the Turtle Key property hosts five private guest cottages. Among the resort’s many features are: a nature walk, common area and boardwalk, pool and ocean porch and grilling area.

Accommodating a wide variety of getaways, events and vacations, the grounds are typically booked for weddings throughout the year. Other pop-up events and activities on the property include: yoga classes, retreats and spa days.

The management team on the grounds plays an active role in making each guest’s stay memorable and enjoyable. In combination with the Virtual Concierge service, they will check-in daily with each cottage to ensure guests are comfortable and have everything they need.

The Turtle Key Channel

The Turtle Key Channel allows guests immediate access to all the water surrounding the island. Many who frequent our cottages choose to bring their boat during their stay, allowing for complete freedom to sail the sea as they please.

If you’d like to arrive by boat, we encourage you to visit our helpful water maps to find the best route.

*Please note: the grounds of Turtle Key have been completely renovated and all housing, furniture and living quarters are sparkling new. As we open our doors to guests, there will be some ongoing construction on varying projects, including the Turtle Key Channel. We thank you for your understanding.