Harold J. Benedict came to the island of St. Croix from Hartford, Connecticut in the early 1920s to work for the St Croix educational system at the request of his future father-in-law, Robert L. Merwin, a local businessman who had himself traveled from the United States to the island of St Croix in the 1870’s. Not long after his arrival on St Croix, Harold, or “Benny” as most people referred to him, met and married Genevieve Merwin, the daughter of Robert L Merwin and his wife, Harriet Armstrong Merwin, daughter of the prominent Armstrong family.

Soon after their marriage on July 3, 1923, Harold and Genevieve (Ben and Gen) moved to Christiansted, where Harold was employed as principal of the Christiansted High school for 19 years. As their family grew, Harold and Genevieve purchased Hannah's Rest Great House and Estate on Centerline Road near Frederiksted, where they raised their family of four children, Harold Jr., Robert L., Patricia and Thomas (Hal, Bob, Pat and Tommy) until1944.

In 1943, Harold Benedict purchased five acres of undeveloped beach land from a Danish man who then owned much of the Smithfield Estate, just south of downtown Frederiksted. Having lived on the island for most of their lives, Genevieve and Harold knew that the beach they had just purchased was the best on the island. Harold only had one leg as a result of World War I and could only swim on this beach since there were few rocks and calm waters.

In the late 1940s, tourism was just taking off on the island with the development of the army airstrip. Tourists were now able to arrive on the island by airplane. In 1949, Harold and Genevieve, with the help of their son Tom, built the first cottage, Coral. The construction of four other cottages, Caribe, Castaway, Calypso, and Cruzan, soon followed Coral cottage. The new cottages were financed in part by ice cream and shell jewelry Genevieve made at the cottages and sold in the town of Frederiksted at night. Some of the shells for the shell jewelry were collected right off the beach. Some of the beach land was also sold to other property developers and to Genevieve's sister, Martha Shultz.

The original five acres of beachfront property is now the land that spans from north of Sandcastle on the Beach Resort to the vacant fenced in land south of Cottages by the Sea. Gen and Ben sold the land north of Sandcastle to a friend of theirs, Bob Schaff, and the land that is now Sandcastle on the Beach to a couple who eventually built The King Frederik Hotel, which was sold and renamed Sandcastle on the Beach in 2001 by the current owners, Cheryl and Simone. Gen and Ben also sold a large plot of land to Genevieve’s sister, Martha, and her husband, John Shultz, who built the cottages that are now Charthouse, Crows Nest, Compass Rose, Caravelle and Commodores Villa. They named their estate Marstrand. We, at Cottages, still refer to those cottages as the Marstrand Cottages. In 2004, the Shultz family decided to sell their cottages to some photographers from New York City who still own the cottages today.

Harold and Genevieve Benedict began to build Cottages by the Sea in 1949 and continued to expand and run the business until1964 when they decided to retire to St Petersburg, Florida with their children. All of the Harold Benedict children were raising their own families in the St Petersburg area, so Harold agreed to lease the property to one of his guests, Mr. Smjeikel. The lease passed to the Little and the McFee families who managed and developed the property for 12 and 21 years respectively. Under the McFee leasehold, more cottages were built and Martha and John Shultz’s home, Marstrand, was also included in the lease.

Gen and Ben built a beachfront home for themselves on the land between the Cottages and The King Frederik Hotel in the 1950’s. They also built another house next door to that house that was used by the leaseholders of the cottages as their residence and office.

Harold J. Benedict died in 1977 and Genevieve M. Benedict died in 1990. Bob and Tom inherited the two houses and the land that lies under Cottages by the Sea after the death of Genevieve and in 2001, Bob decided to sell his portion of the inheritance, the two houses, to the owners who were then purchasing the King Frederik (Sandcastle on the Beach). The new owners of these houses quickly turned Gen and Ben’s house into what is now The Beachside Café’, and the other house into what is now their Villa. As children, the building that now houses the Beachside Café’ was actually “Grandma’s house” to the Benedict grandchildren, where they came to visit with their grandmother Genevieve until just before her death in 1990.

Harold's son, Tom Benedict, moved back to run the family business of Cottages by the Sea in 2001 with his wife, Carol and son, Paul. Tom met Carol on the main patio of Cottages by the Sea in 1958 at a birthday party given for him on the patio by his parents. At the time, Carol was a missionary for the Lutheran church and ran the orphanage in Frederiksted called the Queen Louise Home. They were married in Frederiksted on April 2, 1960 in the Lutheran church. Carol used to take her children from the orphanage swimming on the same beach she now lives on. Carol and Tom also have four children, Patti, Matt, Ruth & Paul. Paul and Ruth both now work for Cottages by the Sea, Paul as the General Manager and Ruth as the reservationist and Marketing Director.

Over the past 50 plus years, Cottages by the Sea has been blessed to attract high quality, loyal guests. Many guests return yearly to escape the cold weather of the north in the winter months, while others study the turtle population or just come to relax and enjoy the beach in the spring and summer.

Many church, school, environmental and military groups have also chosen Cottages by the Sea as their base for lodging. Because of the property's natural beauty, it is common to have guests choose to get married on the beach or spend their honeymoon or anniversary with us as well. Many guests have even chosen to have their ashes sprinkled in the Caribbean Sea in front of Cottages by the Sea.

Despite a few devastating hurricanes and the island's cyclical economy, Cottages by the Sea has continued, and plans to continue, making your Caribbean experience a truly special and enjoyable experience.