Who We Are

A local team, a curated portfolio, and thirteen years of getting the details right.

Our Story

Founded On Hospitality

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.

How We Work

From Booking to Departure, We Handle the Details

At The Holiday Life, we create exceptional vacation experiences in some of Southwest Florida’s most sought-after destinations. Whether you’re planning a quiet family getaway, a sun-soaked celebration, or a season of remote work by the sea, our handpicked homes offer more than just a place to stay. They offer a feeling of home, elevated. From the moment you book to the day you depart, our local team is here to make your stay seamless. Expect beautifully maintained properties, personalized touches, and concierge-style service designed to help you relax, recharge, and make the most of your time away.

Meet The Team

The People Behind the Experience

General Manager

Daniel Dennis

Dan leads with a hands-on, hospitality-first approach, overseeing rental operations and ensuring white-glove service at every step.

Listing Manager

Sydney Allen

Sydney brings over 14 years of real estate experience and a passion for helping properties shine and attract the right guests.

Property Care Manager

Mark Baker

Mark is our boots on the ground, ensuring properties are ready for smooth arrivals and assisting guests whenever needed.

Office Coordinator

Kelly Dunn

Kelly is the first point of contact for guests and owners, bringing seven years of experience and hospitality expertise.

Founder

Casey Potter

Casey founded The Holiday Life in 2013 with a vision to elevate the vacation rental experience in Naples.

Property Services Coordinator

Beth

Beth helps ensure every property is well-maintained and guest-ready, coordinating services across our portfolio.

Social Media Specialist

Lexi

Lexi brings The Holiday Life story to life online, capturing the homes and experiences that make us who we are.

Accounting Assistant

Cyndy

Cyndy keeps our finances running smoothly behind the scenes, supporting the team with precision and care.

Property Services Coordinator

Kiersten

Kiersten works alongside the property services team to keep our homes in top condition for every arrival.

Guest Services Concierge

Theresa

Theresa is dedicated to making every guest's stay special, handling requests and recommendations with warmth.

What We Value

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.