Today we’d like to introduce you to Alison Costello.
Hi Alison, please kick things off for us with an introduction to yourself and your story.
I grew up in Monroe, in the southeast part of the state, and some of my favorite memories were the trips we’d take Up North to visit family and friends. I fell in love with Charlevoix after my uncle bought a cabin there and invited us to spend time in the summers together. From long days on the lake to beach bonfires at night, it quickly became a place that felt special to me—full of charm, energy, and those classic northern Michigan moments.
Early in my career, I moved to Key West, Florida, where I spent several years in hotel management. During that time, I connected with a family who was looking to bring new life to their unique 11-bedroom, 11-bathroom home in Charlevoix. Recognizing the opportunity within the area’s thriving summer tourism market, we refreshed the home’s design and elevated its marketing, transforming it into the Charlevoix Lakeview Home. Today, it serves as a sought-after destination for weddings, family reunions, and group stays throughout the spring, summer, and fall.
Not long after, I was able to purchase my own piece of Charlevoix—a quaint one-bedroom cottage on a small inland lake. Now known as the Charlevoix Lakefront Cottage, it offers guests a quiet, peaceful escape just outside of town.
Since then, we’ve continued to grow. We added the Willow House, a three-bedroom home near Castle Farms that’s perfect for weddings and special events, and we’re excited to welcome a new three-bedroom riverfront home in East Jordan this summer.
For years, my businesses—Welcome Home Charlevoix and Welcome Home Key West—were side projects while I worked as the general manager of a boutique hotel in Key West. But a couple of years ago, when my husband and I were expecting our son, I decided to take the leap into full-time entrepreneurship.
Since then, we’ve expanded our portfolio in Key West, growing the business from nearly the top of Michigan to the Florida Keys. Traveling between the two with a toddler is an adventure in itself, but with the support of my husband and family, it’s been incredibly rewarding.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Every business comes with its challenges. I’ve learned that as an entrepreneur, you have to constantly evolve alongside your business and the industry.
One of the biggest challenges has been running operations remotely. That pushed me to really embrace technology and find tools that help automate and streamline the day-to-day, which has been a huge asset as we’ve grown.
Hospitality, by nature, is also incredibly demanding. You’re “on” for your guests seven days a week—holidays, weekends, even overnight—and burnout can be very real. Over time, I’ve learned how important it is to create balance and make space for myself, not just as a business owner, but as a mother, partner, and friend.
A big part of that has been learning to delegate and trust others. Building a strong team and empowering them to take on different areas of the business has allowed me to focus on what I do best. In a business where you’re always ‘on,’ success isn’t just about growth, it’s about creating something sustainable.
Appreciate you sharing that. What should we know about Welcome Home Charlevoix and Welcome Home Key West?
Welcome Home Charlevoix in Michigan and Welcome Home Key West in Florida are boutique vacation rental management companies, each thoughtfully tailored to reflect the character and expectations of their respective markets.
We curate and manage a collection of distinctive vacation rental properties—from charming waterfront cottages to expansive estates—each thoughtfully designed with its own unique character and refined, comfortable aesthetic. Every home is crafted to deliver a stay that feels effortless, memorable, and distinctly elevated.
Our approach is fully hands-on. We take care of every aspect of the process for homeowners, from design and maintenance to licensing, marketing, reservations, and guest communication. The goal is to make ownership truly seamless, so our clients can enjoy the returns without the day-to-day demands.
In a space often dominated by large-scale platforms and transactional management models, we take a more personalized, boutique approach. That attention to detail shows up in both strong revenue performance and consistently exceptional guest experiences.
How do you think about luck?
Luck and good fortune have absolutely played a role in both my life and my business. I feel incredibly fortunate to have been raised in a supportive, loving family that emphasized education (go Spartans!) and encouraged me to pursue what I love.
That said, I’ve learned the importance of taking smart risks, trusting your instincts, and continuing to learn along the way. Nothing moves forward if you take a backseat in your own life and career—being thoughtfully assertive is what creates momentum and opens the right doors.
Contact Info:
- Website: http://www.welcomehomecharlevoix.com/
- Instagram: https://www.instagram.com/welcome_home_charlevoix
- Facebook: https://www.facebook.com/profile.php?id=61559121269822
- LinkedIn: https://www.linkedin.com/in/alisoncostello/
