Historic Shadow Point

Historic Shadow Point Vacation Rental in Key Largo

History of the Estate

This unique property is an unforgettable slice of 1920s Key Largo. Because of its size and location, Historic Shadow Point is very popular for family gatherings and other special events. We have catered to guests from all over the world, and many come back year after year.

The vintage Cottages are situated on a secluded, shady peninsula surrounded by water on three sides, with clear views of mangrove islands and abundant wildlife. Built-in the 1900s by a sailing ship's captain, each house represents early Keys architecture from the pioneering times of Florida.

History of Hurricanes

In 1926, the first Overseas Highway was under construction  when in September a Great Hurricane struck Miami killing 200 and severely damaging the roadway and bridges being built in the Upper Keys. On October 21 a second hurricane passed just east of the Upper Keys doing more damage to the highway in Islamorada and Key Largo areas.

on September 28, 1929, a Great Hurricane, of which little is written passed through the Upper Keys with estimated winds of 150 mph. Reportedly storm surges were 6-9 feet at Garden Cove. Railroad service was out and sections of the highway were washed out as far as Big Pine Key.

The great Labor Day Hurricane of 1935 had the lowest barometric pressure ever recorded over land in North America. Winds were estimated to exceed 200 mph with storm surge up to 18 feet. With the railroad destroyed a new highway was opened in 1938.

in 1947, 1948 there were several hurricanes that hit the keys, some being as strong as 120mph.

In 1950 they started naming Hurricanes.

On September 10, 1960 Hurricane Donna hit the upper keys at 155mph. It was the worst since 1935.

After Donna 21 years passed before  Floyd, and then Andrew arrived in 1992 on August 24. Our latest was Hurricane Irma in August of 2017.

Despite going through numerous hurricanes the house is still standing which is a testament to the builder and designer of which we know little. This  property was acquired in 1923 by the same family who still own it to this day.  They have worked very hard over the generations to keep the houses as original as possible. The homes are decorated with pieces reflecting the years of being connected to the local waters. Their ancestor, Marvin D. Adams, is responsible for constructing the canal that bisects Key Largo. Known as The Cut to locals, The Marvin D. Adams Waterway allows boaters to travel conveniently from the Atlantic Ocean side to the Gulf of Mexico in minutes. The structures on the property are likely the oldest original residential homes still intact and in use on all of Key Largo. 

Garden Weddings, Beach weddings, Vacation Rental

Orchids abound in the Garden 

Historic Shadow Point Vacation Rental in Key Largo

Vacation Rental on Water in Key Largo - Perfect for Family Gatherings and Weddings.

Historic Shadow Point -Key Largo, Fl

Our Fleet of Kayaks and Paddleboards for guests to use


View of Property and Surrounding Water

cast iron items
replica of a 1920s phonograph
antique bottles

Period antiques of cast iron items, rare bottles, and a phonograph bring you back to the 1920s