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.

Meet The Team

CASEY POTTER

Founder & General Manager

As General Manager, Casey primarily oversees homeowner relationships, strategy, and business development. 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.

STACEY COTTER

Listing Manager

stacey@theholidaylife.com

Originally from Pensacola Beach, Stacey graduated from the University of South Alabama in 2010. Coming from a long line of military, she has lived all over the United States and Europe. and has worked in the real estate industry for over five years. As our Client Services Manager, Stacey is the first point of contact for homeowners interested in listing a property with our company. She works closely with our homeowner clients to introduce them to our program, gather all relevant data on the property to create a thorough and appealing rental listing, and serve as an advisor throughout the rental process. On the weekends, Stacey can be found at the beach with her sons or reading the latest New York Times bestseller. She is an active member of International Association of Women (IAW) and Young Professionals of Naples.

DANIEL DENNIS

Reservations Manager

info@theholidaylife.com

Dan’s role as Reservations Manager is to oversee our guest booking experience, from managing rate strategies to helping match prospective guests with the perfect residence for their stay. He also oversees our concierge service offerings to ensure all of our guests have a rental experience catered to their unique needs. Originally from upstate New York, Dan attended Siena College where he earned a BS in Marketing and Management. After graduation, Dan made the move to sunny Florida for an internship at Walt Disney World before settling in Naples. Dan comes to The Holiday Life from a position as a manager at a luxury boutique hotel in Naples and has a proven track record of exceeding guest expectations and creating memorable experiences. In his free time, you can find Dan "chomping" in support of Florida Gator athletics, kayaking the waterways or exploring the many great dining options in Naples.

ALONDRA TREJO

Guest & Marketing Services

alondra@theholidaylife.com

JANET KLINGMAN

Property Services Coordinator, South Naples & Marco Island

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.

SUSAN MCDONALD

Property Services Coordinator, Central Naples

As a property services coordinator for the downtown Naples area, Susan works closely with the owners of the properties in her portfolio and our cleaning crews to make sure each home is up to our THL standards prior to every rental check-in. She also assists guests with issues or requests they have to ensure their stay is seamless and enjoyable.