Kathleen O’Brien


Kathy hung up her hard hat and work boots from her days working in local government as the Agent for the Conservation Commission in the Metro West Boston area and moved to Fort Myers in 2005. After moving to Ft. Myers, Kathy obtained her Mortgage Broker license. Her specialty was assisting first home buyers achieve their goal of home ownership. That was further emphasized when she obtained her Real Estate license. Kathleen is the mother of three children. Shannon, a successful business woman who resides in the Boston area, Brendan a graduate student at the University of Florida in the study of Physics and Erin who is a graduate of Fort Myers High School and will be attending Florida South Western College this fall to study business. In her free time, Kathy enjoys cooking, gardening and traveling.  Her number one concern is making your Country Club vacation the best it can be!

Daniel O’Brien

Vice President/Broker

Betsy Smith
Director of Operations

Betsy has been associated with the travel business for a number of years. Prior to her involvement in the rental business she managed an upscale luggage and travel accessories store in Nashua, NH for over 20 years. 
She and her husband moved here from New England 16 years ago with the thought of enjoying a quiet retirement. Only a few months into this quest they found themselves to be bored, which led to their involvement in the vacation rental business. Their initial foray in the business was with another rental company for several years. After a brief second attempt at full retirement, which was as equally unsuccessful as the first, they established Country Club Rentals which they successfully owned and operated for eight years. In 2013 they sold the business to Kathy and Dan. Betsy agreed to remain in the office to assist in the transition and continues to provide support to this day.


Beth Colson

Administrative Assistant

 Fenway Frank O’Brien

Senior Security Officer

Fenway has served as the Senior Security Officer for the past three years. Although politically incorrect to share Fenway’s age, he is ten years old and has maintained his boyish figure by patrolling the office tirelessly. You will always be greeted by his friendly smile and disposition. When not on duty, he can be found sharing a chair with Kathy, but don’t be fooled, he has his eye on you and will most assuredly bark at you as you leave the office. We don’t have the heart to tell him he should be barking when you come into the office. Treats are always welcome as he has earned them!!