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Our Company

Our Company

Casey Potter started The Holiday Life in 2013, after noticing a need for high quality, well-managed and easy to reserve rental properties in Naples, a favorite destination she visited often with family and friends. After a brainstorming session with her mom, Lisa, she quickly decided the Sunshine State was calling and left her career on Wall Street to begin managing a small handful of vacation homes.

Our Company

The Holiday Life has grown from there and in 2022, became a John R. Wood Properties company through a merger with the esteemed local real estate firm. Through this synergistic relationship, The Holiday Life continues to improve on Casey’s founding goal of providing a wonderful hotel alternative for local visitors while helping homeowners preserve and create value from their real estate investments.

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Meet The Team

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STACEY COTTER

General Manager

stacey@theholidaylife.com

Originally hailing from the picturesque shores of Pensacola Beach, Stacey is a seasoned professional with a diverse background that has shaped her into a dynamic leader. In 2010, she proudly graduated from the University of South Alabama, marking the beginning of a journey marked by resilience, adaptability, and success. Having roots deeply embedded in a family with a strong military tradition, Stacey inherited a passion for exploration and a commitment to excellence. This upbringing propelled her to live in various corners of the United States and Europe, fostering a global perspective that enriches her professional endeavors. For over seven years, Stacey has been an integral part of the Naples real estate industry, demonstrating an unwavering dedication to her craft. Her leadership style is characterized by a hands-on approach, strategic vision, and an innate ability to navigate the complexities of the rental market. Beyond her professional achievements, Stacey is an active member of the International Association of Women (IAW), where she contributes to a network of like-minded professionals. She is also a dedicated participant in the Young Professionals of Naples, further showcasing her commitment to continuous learning, networking, and community involvement.

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DANIEL DENNIS

Rental Operations Manager

daniel@theholidaylife.com

As Rental Operations Manager, Dan ensures a seamless guest booking experience, managing rate strategies and expertly matching prospective guests with the ideal residence for their stay. He also oversees concierge services, ensuring that every rental is customized to meet each guest's unique needs, creating memorable and personalized experiences. A native of upstate New York, Dan earned his BS in Marketing and Management from Siena College. Following graduation, Dan made the move to sunny Florida for an internship at Walt Disney World, eventually making Naples his home. Prior to joining The Holiday Life, Dan excelled as a manager at a luxury boutique hotel in Naples, where he developed a strong reputation for going above and beyond to delight guests. In his free time, you can find Dan "chomping" in support of Florida Gator athletics, kayaking through Florida's waterways, and discovering Naples' exceptional dining spots.

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MARK BAKER

Rental Operations Coordinator

mark@theholidaylife.com

Born in Boston, Mark moved to Southwest Florida at a young age and is happy to call Naples his hometown! He comes to The Holiday Life after nine years at a luxury boutique hotel in Naples where he brings his guest focused mindset to enhance the rental experience. Mark is our boots on the ground guy making sure properties are ready for a smooth arrival and is always ready to assist guests whenever needed to ensure a comfortable and enjoyable stay. Mark is an avid sports fan and in his free time loves to get in a game of basketball whenever he can, work on projects at his home and spend time with his family.

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KELLY DUNN

Office Coordinator

kelly@theholidaylife.com

Kelly returns to The Holiday Life after working alongside Casey for 7 years bringing a wealth of experience along with a background in the club and hospitality world with her degree in Hospitality Management from the University of Central Florida. As Office Coordinator, Kelly is the first point of contact for both guests and owners as well as assisting with administrative tasks to ensure a smooth operation. Outside of work, she is a proud mother of two and avid traveler, bringing both personal and professional passion to her role.

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JANET KLINGMAN

Property Services Coordinator

janet@theholidaylife.com

As our first and longest standing property services coordinator, Janet is our hostess with the mostest! Her job consists of being out in the field visiting our properties in the South Naples and Marco Island region, performing pre and post-stay inspections to make sure things stay in order from rental to rental. Originally from the Chicago area, Janet brings her midwest work ethic to the table day in and day out, going the extra mile for our guests and our property owners.

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CYNDY FALORIO

Accounting Assistant

cyndy@theholidaylife.com

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CASEY POTTER

Founder

casey@theholidaylife.com

Casey graduated from Georgetown University’s McDonough School of Business in 2010 where she earned a BS in Business Administration with concentrations in Finance and International Business. After graduation, she moved to New York City and spent three years working for the New York Stock Exchange, helping to develop the NYSE Bonds trading platform. Having grown up in West Palm Beach, Casey is a Floridian at heart and is grateful to have the opportunity to live and work in Naples! In her free time, she enjoys spending time at the beach, golf carting around with her golden doodle ‘Winnie’, and boating our beautiful waterways.

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