This week, we are featuring Tom May, founder of Fade Away Vacations. Tom has been partnering his business with OwnerRez since 2022, and what started as a small personal investment has grown into a portfolio of thoughtfully designed homes focused on helping guests “fade away” and create meaningful stays.
Can you tell us a little bit about your history?
Fade Away Vacations started from a simple idea: create places where people can truly disconnect from the noise of everyday life and reconnect with what matters most. What began as a personal investment in a few properties quickly turned into something more meaningful, designing experiences for families, couples, and groups looking to “fade away” for a while. Over time, we’ve focused on building a small portfolio of high-quality homes that prioritize comfort, location, and memorable stays.
What is your background?
My professional background is rooted in technology and consulting, specifically working with organizations to design and implement resilient infrastructure and disaster recovery strategies. That experience translated well into the vacation rental space; systems thinking, process optimization, and attention to detail all play a big role in running a successful operation.
Were you always in vacation rentals or property management? If not, what did you do before?
This is definitely a second career. Vacation rentals started as a side venture and passion project, and over time, evolved into a business. Before launching Fade Away Vacations, I spent years in IT consulting and professional services, helping businesses solve complex infrastructure challenges. That work required a strong focus on reliability, customer experience, and delivering consistent outcomes, skills that directly carry over into hosting and property management.
Are you from the geographical area where your properties are located, or did you move there later?
I’m not originally from all the areas where our properties are located, which gives me a guest-first perspective when selecting and designing each location. Each location was chosen intentionally. We look for areas that offer a unique combination of relaxation, recreation, and accessibility, places we’d personally want to visit, but also areas that tend to create lasting memories for guests. Whether it’s proximity to nature, water, or local attractions, the goal is always the same: help people truly unwind.
What do you love most about the vacation rental business?
The ability to create memorable experiences for people. There’s something incredibly rewarding about knowing a family celebrated a milestone, reconnected, or simply relaxed in one of our homes. It’s not just about providing a place to stay, it’s about being part of someone’s story, even in a small way.
What do you dislike the most about it?
Like any hospitality-driven business, it’s 24/7. Issues don’t always happen during business hours, and there’s always an expectation of responsiveness. Managing that while maintaining consistency across properties can be challenging, but it also pushes us to build better systems and processes.
How do you use OwnerRez to manage your business?
OwnerRez is the operational backbone of our business. We use it to centralize bookings, manage guest communications, automate workflows, and keep everything organized across platforms. It allows us to run a streamlined operation without sacrificing the personal touch guests expect.
What is the most useful feature OwnerRez offers?
Automation and integrations are the most valuable. The ability to automate messaging, scheduling, and operational tasks ensures consistency while saving time. It allows us to focus more on the guest experience rather than getting buried in manual processes.
Tom has done an impressive job of building strong systems that allow him to deliver consistent, memorable stays for his guests. We look forward to seeing Fade Away Vacations continue to grow in 2026!