The original Moorings Village was built in 1936 as a private estate. It consisted of several dwellings; one of them was known as the Main House, the others were its dependencies and guesthouse.
In the 1960’s, Hurricane Donna devastated Islamorada and the Florida Keys. Afterwards, the property was purchased by Mr. Ralph Edsell, Sr., who transformed it into a small resort. The Main House was divided into two apartments and another cottage was built raising the number of accommodations to five.
In 1988, The Moorings was purchased by the present owner and underwent an extensive face-lift and remodeling. It reopened in 1989 under the same name.
In 1989, a piece of land north of The Moorings was the subject of a development scheme which would have consisted of 200 oceanfront accommodations. After a long battle, The Moorings was able to purchase the land, as well as an adjacent piece of property that once housed a disruptive industrial park.
After a year of careful planning, construction plans began to add 14 new cottages. In order to create a sense of harmony, the new cottage architecture does not differ too much from that of the original ones.