Historic Shadow Point

Historic Shadow Point Vacation Rental in Key Largo

History of the Estate

Historic Shadow Point is a rare example of a naturally preserved Floridian ecosystem. A timeless orchid- studded haven of mahogany, buttonwood, lignum vitae, and gumbo-limbo trees. It is the most charming, spectacular, and intimate Family Vacation and event venue in Key Largo, FL. With our own private beach, lovely breezes, tropical gardens, and stunning 180 degrees of Largo Sound vistas, there is no better place for an unforgettable family get-together or event.


 Mr. Frank Sweeting from Bloomington, Illinois bought this property in the 1920s because of his love for fishing and warm weather. He bartered, entertained, and had many of his cronies and public figures to Key Largo to experience the excitement, the ambiance, and of course, his passion catching fish and gambling. Located on over two secluded acres in the Florida Keys, it is nestled in a native hardwood hammock and has been owned by the same family since 1923.

The two vintage Cottages on the property will sleep 12 to 16 guests.  Conveniently located one hour south of the Miami International Airport, Historic Shadow Point is an unmatched vacation rental opportunity and event venue. There's no place like it!

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.

The property was acquired by the same family who still owns 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

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Historic Shadow Point

5107 SW Anhinga Ave.

Palm City, Fl 34990


Mile Marker 103

598-601 Bonito Ave.

Key Largo, Fl.

Orchids at Historic Shadow Point Key Largo