What Makes a Vacation Rental Brand Memorable? (It's Probably Not What You Think)

I've stayed in a lot of vacation rentals over the years.

Some have been beautiful beach houses with incredible views. Others have been cozy cabins tucked away in the mountains. I've stayed in luxury resorts, tiny cottages, boutique hotels, and just about everything in between. If I'm being honest though, many of them have blended together over time.

But every once in a while, you visit a place that quietly changes the way you see hospitality.

For me, that place was a little boutique hotel in Costa Rica called Sebu.

Looking back, it's funny because I couldn't tell you what kind of mattress we slept on or whether the bathroom had double sinks. I don't remember the thread count of the sheets or if it had a hot tub or not. Those are the things we spend so much time talking about as vacation rental owners, yet they aren't the things that stayed with me.

What I remember are the moments.

Every morning began with locally roasted coffee that had been grown just down the road. It wasn't simply left on the counter as another amenity. The hotel invited guests to visit the local coffee farm and see where it all began. That simple cup of coffee suddenly had a story, and somehow it tasted even better because of it.

Locally grown coffee and chocolate tour in Costa Rica

Not far from the hotel, we visited a local cacao farm where we learned how chocolate is made from start to finish. We walked through the process, met the people behind it, and left with a whole new appreciation for something most of us take for granted. It wasn't just another activity to check off our itinerary. It felt like we had been invited into a small piece of their community.

Even the little details reflected where we were. The soaps and shampoos were locally made. The restaurant featured fresh ingredients from nearby farms. Instead of pointing us toward the most popular tourist spots, they shared places the locals genuinely loved.

One of my favorite memories was a little restaurant where we met Paco, the resident dog who seemed to greet everyone as if they were old friends. We found ourselves returning to Jungle Bowl more than once, partly because the smoothie bowls were incredible, but mostly because we loved chatting with the owner while her young daughter played nearby (if you know me, you know I will take every opportunity I can to learn about someone’s story). Those interactions lasted only a few minutes, but somehow they became part of our story too.

And then there was the airplane.

Tucked away in the middle of the jungle was an old airplane that had been transformed into one of the most unique places you could stay. It felt adventurous, unexpected, and completely connected to its surroundings. I still find myself telling people about it.

The more I think about that trip, the more I realize none of those memories had anything to do with luxury.

They had everything to do with connection.

Connection to the people. Connection to the culture. Connection to the landscape. Connection to a story that could only be told there.

I don't think I realized it at the time, but that trip quietly changed the way I thought about hospitality. It also changed the way I approach branding.

Before Costa Rica, I probably would have described a great vacation rental by its amenities. After Costa Rica, I started asking a completely different question.

WHAT STORY CAN BE TOLD HERE?

That question has become the foundation of every brand I create today.

One of the biggest misconceptions I see in the vacation rental industry is that branding begins with a logo. While I absolutely love designing beautiful visual identities (cause that's totally my jam!), I've learned that a logo isn't where memorable brands begin. It's simply the visual expression of a much bigger story.

The strongest brands begin by understanding the people they're inviting in and the experience those guests are hoping to have.

That's the mindset shift that has shaped my entire business.

Guests aren't booking a place to stay.

They're booking the transformation they hope to experience.

They're booking uninterrupted conversations around the dinner table after months of busy schedules. They're booking slow mornings without alarms, adventures they'll talk about for years, and the chance to reconnect with the people they love most.

Your property becomes the setting where those memories unfold.

It's funny because when I first started designing brands, I thought my job was to create something beautiful. Looking back now, I realize that's only a small part of it. My real job is helping STR hosts uncover the story that's already there. The logo, the colors, and the website simply become the way we tell that story.

When I begin working with a branding client, we spend surprisingly little time talking about logos. Instead, we talk about their dream guests. Who are they? What inspired this trip? What are they hoping to leave behind for a few days? How do they want to feel when they return home?

Those conversations shape everything that follows. The photography feels more intentional. The website tells a richer story. The welcome guide becomes more personal. Even the smallest details begin working together to create an experience guests will remember long after they've unpacked their suitcases.

Maybe that's why I still tell people stories about our stay at Sebu after all this time.

Not because it was the fanciest place I've ever stayed, but because it reminded me that the most memorable destinations aren't defined by all the amenities they have. They're defined by how they make people feel.

And I think that's what great branding is really about.

Looking back, I think Costa Rica gave me much more than a memorable vacation.

It changed the questions I ask every time I begin working with a new client.

We don't start by asking what logo fits their property or what color palette feels on trend. We start by thinking about the story they're creating and the experience they want their guests to have.

And maybe that's the goal for all of us.

Not to create a property that's more impressive than everyone else's, but to create an experience that couldn't happen anywhere else.

An experience so connected to the people, the place, and the story that guests carry a little piece of it home with them.

If you're reading this and realizing you don't actually know who your dream guest is yet, you're not behind. That's genuinely the very first conversation I have with every single client, before we ever talk logos or colors or websites. I loved that first step so much that I turned it into something you can walk through on your own. It's called the Dream Guest Workbook, and it's free! It asks you the same questions I'd ask you over coffee if we were sitting down together, so you can get clear on exactly who you're creating this experience for before you touch a single design decision.

So now, one of the questions I find myself coming back to again and again is this:

What story will your guests still be telling years from now? Because I think that's the foundation of a truly memorable brand.