Enjoy a Little Piece of Paradise

Escape from reality and treat your mind, body, and soul to a relaxing and rejuvenating Caribbean island vacation in the pristine Cayman Islands. Head O' Bay is a beautiful beachfront home located on 10 acres of land on Little Cayman in the Caribbean Islands. Little Cayman lies 120 miles west of Jamaica and are exclusive, beautiful islands known for sandy white beaches and relaxing, laidback environment.

Little Cayman is known as one of the best scuba diving locations in the world. Guided Deep sea and Bay fishing is available at Head O' Bay through the Little Cayman Fishing Club. Go to the LCFC page for rates and policies, and learn more about the excisting fishing adventures that lie ahead!  Whether you want to spend a week of lounging in hammocks on the beach or you are ready for an adventuresome vacation full of activities, choose Head O' Bay and discover paradise.

About Us

At Head O' Bay, we are a family-owned-and-operated business and we have been renting our private home in the Cayman Islands for 6 years. The home was specifically built for vacation rentals and our goal is to provide families and couples with a fun, relaxing, and affordable vacation.


There's no other place on earth I'd rather be than having breakfast on the terrace at Head O'Bay.

Rich and Bev Jerdan