From Wedding Venue Dreams to Airbnb Success: Our Kentucky Property Pivot

A Pattern of Unintentional Rentals

A few weeks ago, I shared the story of our very first short-term rental—our North Carolina home that was never meant to be a rental at all. Today, we’re continuing down that path with a deeper look into our Kentucky property, which followed a surprisingly similar trajectory.

Much like our first home, our Kentucky property wasn’t intended to be a short-term rental. In fact, when we purchased it in 2021, our grand vision was to turn it into a luxury wedding venue.

The Vision: A Dream Wedding Venue on 90 Acres

The Kentucky property is stunning—set on 90 acres with a 6,000-square-foot main house featuring five bedrooms and five and a half bathrooms. It was ideal for hosting full-weekend wedding guests. We had every intention of making it a beautiful and profitable event space.

We did our best due diligence before submitting an offer. Within weeks of closing, we started the conditional use permitting process, which kicked off in August 2021. We ultimately did get the permit to run a wedding venue, but with 18 restrictions—an unusually high number. Most local venues had one or two. The challenges mounted, and by April 2022, nearly nine months after the purchase, it became clear that the wedding venue dream wasn’t going to work the way we had hoped.

Pivoting the Plan: Turning to Short-Term Rentals

We had a difficult decision to make: sell the property or repurpose it. Fortunately, our existing permit allowed for overnight guests as part of the wedding hosting plan. So we pivoted and launched it as a short-term rental instead.

The property included a secondary structure known as the carriage house: an apartment above a garage, roughly 1,000 square feet with two bedrooms and one bath. In May 2022, my family moved into the carriage house while I was expecting our third child, due that August. We began setting up the Airbnb listing and welcomed our first guests in July 2022.

Challenges from the Start

Our early Airbnb days were anything but smooth. We faced pushback from neighbors who argued that the overnight guest permit applied only to weddings, not traditional short-term rentals. So we had to apply for an additional conditional use permit in June or July 2022.

To complicate matters, I had an unplanned emergency C-section just as our Airbnb was ramping up. We had to block off dates to allow for recovery in the main house, which was more accessible than the upstairs carriage apartment.

Key Lessons Learned

1. You can never do too much due diligence.
We thought we’d done our homework—talked to the zoning office, researched nearby venues, and evaluated the county’s conditional use policies. But our permit ended up being far more restrictive than anticipated. The lesson? Research not just the legalities, but also the community mindset.

2. Understand the local community culture.
Our county was rural and resistant to outsiders, especially when it came to new business and outside guests. Had I joined local Facebook groups beforehand, I might have picked up on the sentiment sooner. It’s now a step I always recommend when considering an investment property.

3. Attractions alone aren’t enough.
Our location seemed ideal—central to Kentucky’s famous Bourbon Trail, near Louisville, Lexington, Frankfort, and Bardstown. But attractions aren’t everything. Even a great location can struggle if the community isn’t aligned with your business goals.

Designing with Purpose: How Branding Lives Inside the Walls

When I started designing The Commonwealth, I really wanted the brand to come to life inside the walls of the property—not just in the name or the logo, but in the actual guest experience. Each of the four ensuite bedrooms was designed around the concept of the four U.S. Commonwealth states: Virginia, Kentucky, Pennsylvania, and Massachusetts.

In the Pennsylvania room, for instance, I leaned into the state’s palette of blush pink and navy blue. I added blush accent pillows, a navy blue comforter, little touches that pulled directly from the state’s identity. These small details might not scream “brand” at first glance, but when you know the story behind them, they make everything feel cohesive and intentional.

The Virginia room was special to design because that’s where I’m from. I drew a lot of inspiration from Colonial Williamsburg. Deep greens, traditional touches, and a beautiful dark green dresser that anchored the room. I also incorporated pink dogwood accents (Virginia’s state flower) through pillows and textiles.

And in the Kentucky room, which is the primary suite, I wanted to nod to the equestrian heritage without being too on-the-nose. The previous owners had left behind a beautiful antique furniture set in a golden velvet fabric with dark wood accents—perfectly in line with Kentucky’s state flower, the goldenrod. It added that local touch in a way that felt elevated, not kitschy.

All of these design decisions helped me shape a short-term rental that stood out—and more importantly, told a story. When guests walk through the home, they’re not just entering a place to sleep; they’re entering an experience.

Launching the Rental and Maintaining Momentum

July 2022 is when we officially opened up booking for The Commonwealth. I was nine months pregnant at the time (baby number three was due in August!), and we hit the ground running with three bookings in the first week. That initial momentum was helped by Airbnb’s algorithm, which favors new listings but we’ve managed to keep our listing near the top ever since.

I’ve been hosting on Airbnb since 2018 and have never lost my Superhost status. One of my go-to strategies for maintaining a perfect five-star rating? I send guests a follow-up message shortly after checkout around 1 PM.

Hosting Through Challenges—and Remotely

Aside from a few short breaks right after I recovered from an emergency C-section in August 2022, and again in February 2024 after another surgery, we’ve had near-constant bookings. When we moved away from Kentucky in March 2024, we transitioned to managing the property remotely.

Luckily, we found tenants to live in the guest house, which has been a huge help. I still manage all the booking, scheduling, and coordination, but they’ve stepped in for the occasional emergency or one-off task. For example, we had a rare same-day turnover that coincided with a toilet issue. The plumber had to remove the toilet and left behind a small mess but the tenants were able to double-check everything before the next guests arrived. It all worked out, but having that extra set of eyes made a huge difference.

Managing remotely isn’t always perfect, but it has gone smoothly overall. It’s sparked a real passion in me to expand into co-hosting. If you or someone you know is looking for a short-term rental co-host, I’d love to be considered. I’ve been doing this for nearly seven years, and I’ve developed systems that run efficiently and profitably even from afar.

Getting Clear on Our Ideal Guests

Initially, when I designed the home, I envisioned a bride as the end-user since it was meant to be a wedding venue. But now that we’ve been running The Commonwealth as a short-term rental for several years, it’s become clear who our ideal guest actually is.

Our typical guests are usually groups of adult couples, lifelong friends who are reuniting. Sometimes they met in college or high school, sometimes through their kids, but they’re using our home to catch up and enjoy the Bourbon Trail together. It’s often been a year, five years, even ten years since they’ve all been together. Our home gives them the space and setting to reconnect.

Nearly all of them incorporate Bourbon Trail experiences into their trip. So, I’ve built a few touchpoints into the guest experience to make that as smooth and enjoyable as possible:

Upon arrival, guests receive a printed Bourbon Trail guide in the home. Even if they’ve already booked tours, they love flipping through and seeing what else is nearby.

At booking, I send them contact info for local tour bus companies, so they can enjoy the bourbon without worrying about driving.

Before check-in, I share my personal recommendations based on the kind of traveler they are. Some guests are bourbon connoisseurs. They know their mash bills, tasting notes, and favorite distilleries. Others are just along for the fun (I’m this type!). We offer customized suggestions for both.

All these touches are part of what makes our property not just a place to stay, but a destination.

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Ready to Elevate Your Brand or Rental?

If you’re a fellow host looking to elevate your rental experience or a realtor aiming to clarify your personal brand, I’d love to help. I’m linking that Power Hour booking page again in the show notes, along with the original episode on the wedding venue zoning saga for those who want the full backstory.

Thanks for following along and for walking down memory lane with me.

A Quick Note: Let’s Tackle Your Branding Together

If you’re feeling stuck with your branding or marketing strategy—whether you’re a realtor, a short-term rental owner, or somewhere in between—I’d love to invite you to book a Power Hour session with me. It’s a focused, one-on-one video call where we dive straight into your challenges and map out tailored solutions.

You can find the link to book in the show notes. Let’s turn your ideas into intentional action.