Richard Veale
Owner and Real Estate Broker

Richard has previously owned a large vacation home rental business in the Orlando area and comes with a wealth of experience with the rental of investment properties and will be focusing on developing some more out of season rentals as well as keeping the homes fully booked through the season.  

Richard has been a Licensed Florida Real Estate Broker since 2005 and will always be available to help and advise on Real Estate services as well if needed in the future. Country Club Rentals is now introducing Home Watch services for  any of our owners that does not currently have this service we would be happy to share the benefits of this service of this offer to protect your investment. 

Richard is originally from the U.K. and relocated to Florida in 2004 and looks forward to working with you all. 

We are proud to say that Country Club Rentals still remains the only rental and property management company  in the area and we are respected throughout the industry. 

We all look forward to our ongoing relationships with you all.


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.  Kathy previously owned Country Club Rentals, Inc. from 2013 to September of 2017 and has remained to assist where needed.

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 is 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!

Betsy Smith

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 O'Brien and Dan O'Brien. Betsy agreed to remain in the office to assist in the transition and continues to provide support to this day.