Founded in 2013 by Casey Potter, The Holiday Life was born from a vision to elevate the vacation rental experience in Naples by combining beautiful properties with professional, hospitality-driven service. What began with a small collection of homes has grown into a trusted name in luxury rentals across Naples and Marco Island.
Now a proud part of John R. Wood Properties, The Holiday Life continues to lead the industry in personalized service and premium coastal escapes. As the unrivaled leader in the local vacation rental market, we provide a seamless alternative to traditional hotels—focused on high-touch care for both our homeowners and guests. Our approach is rooted in hospitality, with every detail thoughtfully managed to deliver comfort, ease, and unforgettable stays.
Values That Guide Every Experience
Hospitality at the Heart
Everything we do is centered around creating meaningful, memorable experiences—for our guests and our homeowners alike.
Local Roots, Insider Knowledge
As proud locals, we bring a deep understanding of Naples and Marco Island—and a personal touch that only comes with being part of the community.
White-Glove Service
From seamless bookings to beautifully prepared homes, we handle every detail with care, professionalism, and a commitment to excellence.
Trust Built Over Time
We value long-term relationships, built on consistency, integrity, and doing right by our clients, always.
Curated for Coastal Living
We don’t just rent homes—we design escapes. Every property and experience is selected to reflect the best of luxury coastal life.
Always Evolving
We stay inspired by new ideas, tools, and trends to ensure our service and offerings stay fresh, relevant, and top-tier.
Meet The Team
DANIEL DENNIS
General Manager
daniel@theholidaylife.comAs General Manager of The Holiday Life, Dan leads with a hands-on, hospitality-first approach—ensuring both guests and homeowners receive white-glove service at every step. He oversees the full spectrum of rental operations, from dynamic pricing strategies and team leadership to property performance and owner relations. Dan’s focus is on creating a seamless experience for our homeowners while maximizing the value of their investment and delivering memorable guest stays. A native of upstate New York, Dan earned his BS in Marketing and Management from Siena College before heading south for an internship with Walt Disney World. He quickly fell in love with Florida living and made Naples his permanent home. Prior to joining The Holiday Life, Dan managed a luxury boutique hotel in Naples, where he built a strong reputation for exceeding expectations and crafting personalized experiences for discerning guests. Outside of work, Dan loves to travel and draw inspiration from new places and experiences. He’s also a die-hard Florida Gators and Miami Dolphins fan—don’t be surprised to find him fully decked out in team gear on game day, whether he's cheering from the stands or the couch. When he's not traveling or rooting for his teams, Dan enjoys kayaking Florida’s scenic waterways and discovering the best of Naples’ vibrant dining scene.
SYDNEY ALLEN
Listing Manager
sydney@theholidaylife.comAs Listing Manager, Sydney brings over 14 years of real estate experience and a passion for helping properties shine. She handles everything from listing strategy to photos and descriptions, ensuring each home attracts the right guests and delivers strong results. With a sharp eye for detail and a team-focused approach, she’s all about creating great first impressions that lead to memorable stays. Originally from Indiana, Sydney brings Midwest warmth and real estate savvy to sunny Florida. Before joining The Holiday Life, she built a successful career in real estate, honing her skills across the industry and earning a reputation for professionalism, approachability, and always going the extra mile. Outside of work, she’s a proud Cat Mom, lifelong Disney World fan, and a die-hard Colts supporter (yes, even during rebuilding seasons!). You’ll often find her boating, relaxing at the beach, or catching Florida’s gorgeous sunsets with friends and family.
MARK BAKER
Rental Operations Coordinator
mark@theholidaylife.comBorn 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.
KELLY DUNN
Office Coordinator
kelly@theholidaylife.comKelly 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.
CYNDY
Accounting Assistant
BETH
Property Services Coordinator
THERESA
Guest Services Concierge
LEXI
Social Media Specialist
CASEY POTTER
Founder
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.