Meet the Team Behind Deserving Vacations

Locally managed. Personally cared for.

Deserving Vacations was built on a simple belief: vacation rental management can be done better — with stronger relationships, more personal service, and genuine hospitality at the center of it all.

That belief has guided us since 2009.

Today, Deserving Vacations has grown into a team of local professionals who know the Charleston area, know our properties, and genuinely care about the owners and guests we work with. We've grown quite a bit over the years, but we've been intentional about staying boutique, accessible, and hands-on.

Because to us, great property management has always been personal.

Nathan Bullock

Founder, CEO & Co-Owner

Deserving Vacations is Nathan's baby.

Originally from Okemos, Michigan, Nathan is a proud Michigan State University graduate who made his way south to Charleston in 2004. A year later, he began what would become a lifelong career in hospitality at Wild Dunes Resort.

Nathan started as a Reservations Associate in 2005, learning the guest side of the vacation rental business from the ground up. He moved into property management in 2007 and then into housekeeping management in 2008. Those years gave him a firsthand look at nearly every side of vacation rental management — from the guest experience to property care and, most importantly, the relationships with homeowners.

And he saw an opportunity.

Nathan knew there were vacation homes that had yet to reach their potential. More than that, he believed property owners deserved a management experience that was more personal, attentive, and invested in their success.

So in 2009, he founded Deserving Vacations.

Nathan grew the company slowly and intentionally over its first decade, focusing on relationships, quality, and doing right by the owners who trusted him with their homes.

Then came 2020.

Like so much of the hospitality industry, Charleston's vacation rental market came to a halt when COVID arrived. But when travel returned, it returned in a big way. Since then, Deserving Vacations has more than doubled in size.

The company may be bigger today, but Nathan has never wanted it to feel bigger. Maintaining the relationships and level of service DV was built on remains incredibly important to him.

More than 17 years after starting the company, Nathan is still very much at the center of it. He's our problem solver, our sounding board, our steady hand, and the person who keeps us focused on why Deserving Vacations exists in the first place.

He's the backbone of all things Deserving — and we wouldn't have it any other way.

Holly Bullock

CFO & Co-Owner

Holly's path to Deserving Vacations wasn't quite as direct — but looking back, it makes a lot of sense.

Born in Cincinnati, Ohio, Holly graduated from Tiffin University in 2007 and spent her first year after college working as an IT technical recruiter. Ready for a change of scenery, she packed up and moved to Charleston in 2008.

Her first stop? Wild Dunes Resort.

Holly began as a Resort Ambassador, where she got her first taste of the hospitality industry — and happened to meet Nathan along the way. She later moved into Human Resources before beginning a career that would ultimately blend HR, technology, operations, and customer service.

In 2009, Holly joined Benefitfocus, where she discovered how much she enjoyed the intersection of people, technology, and service. That experience eventually led her into healthcare technology, including seven invaluable years with Cincinnati Children's Hospital Medical Center, where she grew from an HRIS role into a consulting position.

She later joined CommonSpirit Health, continuing her work in technology and innovation, and ultimately served as an Innovation Lead Analyst.

Then, in 2021, Deserving Vacations came calling.

The company was growing quickly, and Nathan needed another set of hands — preferably someone who understood HR, technology, operations, customer service, and the business itself.

Fortunately, he knew someone.

Holly joined Deserving Vacations full-time in August 2021. She'll be the first to tell you she isn't particularly interested in titles, but since every company apparently requires them, CFO seemed to fit best.

In reality, her role covers a little bit of everything: company financials, owner relations, new-owner onboarding, payroll, technology, the website, marketing and social media — along with whatever else happens to land on her desk that day.

Her background may look a little unconventional for vacation rental management, but that's exactly what makes it valuable. Holly brings the systems, service mindset, and operational experience that help Deserving Vacations continue to grow without losing the personal approach that made it successful in the first place.

A Family Business, in a Place We Love

Somewhere between all those years at Wild Dunes and building Deserving Vacations, Charleston became much more than the place Nathan and Holly had each independently decided to call home.

It became their place.

Nathan and Holly were married on Sullivan's Island in 2013, followed by a reception at the Citadel Beach House on Isle of Palms. So, yes — you could say this little stretch of the Lowcountry is pretty special to them.

Today, they live in Mount Pleasant with their three children, Evie, Calvin and Rowan, and their dog, Clyde.

Deserving Vacations has grown alongside their family. What started with Nathan, a handful of properties, and an idea for doing things differently has become a team they're incredibly proud of.

And through every stage of that growth, the goal has stayed remarkably simple:

Take great care of our owners. Take great care of their homes. Take great care of our guests.

That's Deserving Vacations.