Today we’d like to introduce you to STEPHEN JOHNSON.
Hi STEPHEN, we’d love for you to start by introducing yourself.
My story with short term rentals actually started about ten years before I ever owned one.
In 2015, my wife Joelle and I had two young daughters, 8 and 6. Up until then we had done a lot of camping as a family, but we had never really taken what I would consider a true family vacation. We didn’t have a lot of extra money at the time, but we decided we were going to make it happen. We chose Destin, Florida, where I grew up, and decided to drive down to save money instead of flying.
I spent hours looking at hotels trying to find something with an efficiency kitchen, or at least a microwave and refrigerator. With two young kids, eating out three meals a day for an entire vacation just wasn’t in our budget.
Somewhere during that search, I stumbled across VRBO. I had never heard of it and honestly didn’t even know that regular people rented out their condos and vacation homes to other families. I started looking through the properties and couldn’t believe what I was finding.
We ended up finding a fantastic condo across the street from the beach. When I sent the booking request, I told the owner a little about myself, my wife and our girls and that this was really our first family vacation. His name was Dave, and he lived in Michigan. I still remember his name more than ten years later.
Dave accepted our reservation, and that experience planted a seed with me that never really went away. I loved the idea that you could own a place your own family could enjoy while also opening it up to other families and giving them a place to make their own memories. I also loved that there was a real person on the other side of the reservation. Even back then, I remember thinking that someday I would love to own a vacation rental of my own.
That trip also completely changed the way our family traveled. From that point forward, we became vacation rental people. Over the next ten years, we stayed in VRBOs and Airbnbs two or three times a year. We had some incredible experiences and, like anyone who travels enough, some not so great ones. We also stayed in properties that were personally managed by the owner and others managed by larger property management companies. As a guest, I could absolutely tell the difference.
All those years of being a guest shaped what I eventually wanted to create. Long before I became a host, I spent years being a guest.
Fast-forward to 2025, and my wife and I were finally in a position to make that idea from 2015 a reality. We purchased a two-bedroom condo in Myrtle Beach, South Carolina, that we named Waterway Retreat. We live in New Hampshire, so deciding to self manage a vacation rental hundreds of miles away probably wasn’t the easiest way to get started, but I knew I wanted to be personally involved in the guest experience.
What I didn’t expect was how much I would fall in love with the hospitality side of it. It became much more to me than owning a condo and renting it when we weren’t using it. I became obsessed with learning the business, guest communication, pricing, cleaning and maintenance, marketing, technology, direct bookings and all the little details that can turn a good stay into a great one.
Today, Waterway Retreat has grown into its own small brand with its own direct booking website and a growing number of repeat and direct guests. But the part I’m most proud of is the experience we’ve been able to provide families who stay with us.
In a lot of ways, I still think about that first trip to Destin. Back then, I was the dad trying to figure out how to give his wife and two little girls a great vacation without spending money we didn’t have. Today, when a family books Waterway Retreat, I know there may be another dad or mom on the other side of that reservation trying to do exactly the same thing.
That’s something I never want to lose sight of.
We all face challenges, but looking back would you describe it as a relatively smooth road?
I wouldn’t say it’s always been a smooth road, but overall, it’s been a really rewarding learning experience.
One of the biggest things I learned early on is that owning a short term rental and operating one well are two very different things. After spending so many years as a guest, I knew the type of experience I wanted to provide, but there was still a lot to learn about everything that happens behind the scenes.
One unique challenge for us is that we live in New Hampshire while Waterway Retreat is in Myrtle Beach. I chose to self manage because being personally involved with our guests was important to me, but that also meant finding great local people I could trust and putting systems in place so that we could take care of things quickly even when I’m hundreds of miles away.
There has also been a learning curve on the business side. Myrtle Beach has a lot of vacation rentals, so simply having a nice condo doesn’t mean people are automatically going to find or book it. I’ve had to learn about pricing, seasonality, marketing, photography, direct bookings and how to reach the types of guests who are a good fit for our property.
Of course, things occasionally go wrong. An appliance can break, something can get missed during a turnover or a maintenance issue can come up unexpectedly. I’ve learned that you can’t prevent every problem, but you can control how you respond to it. I try to be available, communicate honestly and take care of things as quickly as possible.
Probably the biggest challenge for me personally is that I’m always looking for ways to make things better. I’m constantly learning, trying new ideas and figuring out what works and what doesn’t. More recently that has included building our direct-booking website and finding ways to create relationships with guests that go beyond a single stay.
There have certainly been challenges along the way, but they’ve been part of the experience. I’m still learning all the time, and I think that’s actually one of the things I enjoy most about it.
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
My full time career is actually very different from the vacation rental world. I work in automation and maintenance leadership for a large distribution operation, where I lead teams responsible for maintaining complex automated equipment and keeping operations running.
I’ve spent much of my career in maintenance and leadership roles, so problem solving, planning ahead and building reliable systems have become second nature to me. I think a lot of that has carried over into how I manage Waterway Retreat.
With a short-term rental, especially one that I manage from several states away, you have to be proactive. I try to think about what could go wrong before it does, have good people and processes in place, and respond quickly when something unexpected happens. My professional background has definitely helped me approach the property that way.
At the same time, hospitality has brought out a completely different side of me. At work, success might mean solving an equipment problem or helping a team perform better. With Waterway Retreat, success can be as simple as getting a message from a family telling me how much they enjoyed their vacation. I’ve found that incredibly rewarding.
What I’m probably most proud of professionally is the reputation I’ve built as someone who cares about doing things the right way and takes ownership when something needs to be done. That’s something I’ve tried to carry into Waterway Retreat as well. I don’t look at our guests as reservation numbers. They’ve trusted us with part of their vacation, and I take that responsibility seriously.
In terms of your work and the industry, what are some of the changes you are expecting to see over the next five to ten years?
I think the short term rental industry is going to continue to grow over the next 5–10 years, but I also think it’s going to become much more competitive and professional.
There was a time when someone could buy a vacation property, put it on Airbnb or VRBO, take a few decent pictures and expect the bookings to come. I think those days are quickly disappearing. There are simply too many choices now, and guests have become much more experienced with vacation rentals and know what a good stay should look like.
I think that’s going to put much more emphasis on the actual guest experience. Cleanliness, communication, consistency and the little details are going to matter even more. A beautiful property will always help, but I don’t think the property alone will be enough. Owners and managers are going to have to give travelers a reason to choose them over hundreds of other options.
I also think we’ll see more owners trying to build an identity outside of Airbnb and VRBO. The large platforms will continue to be important, but direct booking, repeat guests, email marketing and building an actual brand are going to become a bigger part of the business. That’s something I’ve only recently started working on with Waterway Retreat, and I’ve already seen how valuable it can be.
Technology will obviously continue changing the industry as well. AI, automated messaging, dynamic pricing and smart-home technology can make operating a short term rental much easier. I use quite a bit of technology myself, especially since I manage from New Hampshire, but I think there’s a balance. Technology should make hospitality easier; it shouldn’t replace the personal side of hospitality.
For me, that’s where I think the opportunity will continue to be. As the industry becomes more automated, there will still be value in knowing there is a real person behind the property who genuinely cares about your stay.
Maybe that’s because my first experience with a vacation rental was with an out of state owner who’s name I still remember over 10 years later. I think that says a lot about where I hope this industry doesn’t lose its way.
Contact Info:
- Website: https://Waterwayretreat.com
- Instagram: https://www.instagram.com/staywaterwayretreat/
- Facebook: https://www.facebook.com/CoastalCarolinaGetaway/
