SEPTEMBER 30, 2025
#152 Vacation Rental Success: How Allison Bayley Built a 66-Property Powerhouse
What does real vacation rental success look like?
For Allison Bayley, it meant transforming her family’s real estate legacy into a thriving business—one that now manages 66 properties and dominates its market. And here’s the kicker: she started with grit, a tiny 600-square-foot office, and a whole lot of late nights bartending to make it happen.
Her story is living proof that age, background, or appearances don’t define you—passion and persistence do.
The Road to Vacation Rental Success
Allison’s path was anything but traditional. From summers at her grandparents’ campground to scuba diving in California, she didn’t set out to run a vacation rental company. But when her mom, a real estate agent, called her home with a bold idea, Allison took the leap.
What followed was a crash course in entrepreneurship—long hours, uncomfortable risks, and learning to trust her vision even when others doubted her.
Today, her company is a women-owned, women-operated powerhouse redefining what a family business looks like in the modern hospitality landscape.
Breaking Barriers in the Vacation Rental Industry
As a young, tattooed, non-traditional professional, Allison faced plenty of skepticism. But instead of letting it slow her down, she used it as fuel to prove the doubters wrong.
Here’s what set her apart:
- A cutting-edge tech stack to streamline operations.
- A fierce focus on guest experience that built loyalty and trust.
- A bold mindset that turned obstacles into opportunities.
This mix of strategy and resilience is the essence of vacation rental success.
Lessons Every Host Can Learn
Allison’s story isn’t just inspiring—it’s actionable. Whether you’re managing two properties or dreaming of 20, here are her takeaways:
- Start where you are—even if it’s in a 600-square-foot office.
- Build systems that scale with you.
- Don’t let appearances or industry stereotypes define your path.
- Keep guest experience at the heart of your business.
Wrap-Up
Vacation rental success doesn’t come from luck—it comes from courage, persistence, and a willingness to take risks others won’t. Allison Bayley’s story proves that when you pair vision with hard work, you can build something extraordinary.
Whether you’re at the very beginning or well on your way, her journey is your reminder that the future of your business is bigger than you think.
HIGHLIGHTS AND KEY POINTS:
[01:08] A short introduction about our guest Allison Bayley and how she got into short-term rentals
[03:14] How Allison’s mom’s phone call felt like the right moment to return home and take on more responsibility
[04:47] Allison shares how she and her mom set up the vacation rental business in the early days
[07:43] Allison reflects on the early fatigue and mental strain of building her business while juggling long shifts in hospitality
[10:52] Allison shares how she faced misjudgments for her tattoos, piercings, and colored hair and the way she navigated those perceptions
[15:41] How Allison’s early responsibility and guidance from her sister and therapist shaped her emotional resilience and wisdom
[18:26] Allison’s perspective on what makes a good boss and recalls lessons from a former mentor about keeping doors open and not burning bridges
[19:47] Allison talks about her all-female, close-knit team and the challenges of balancing friendship with leadership in her seasonal business
[28:42] Allison describes her evolving use of systems and technology to streamline operations and manage growth
[32:54] Allison shares her evolving perspective on team feedback, communication tools, and embracing growth through discomfort
[37:15] Allison’s post-season shift in strategy and vision for guest experience and future concierge services
[39:46] The lightning round
Golden Nuggets:
- “They say, mind over matter, and that’s where I really just had to often remind myself, is mind over matter. And having a good mindset around it is what is required to continue on.”
- “The grass is only greener where you water it.”
- “Training our brains to actually recognize when those negative thoughts are happening in real time and rewinding and rewiring them to shift them to positive thinking is one of the best gifts you can give yourself.”
- “You cannot control other people’s actions. You can only control your reaction.”
- “A good boss to me is someone that you can rely on, and someone that you know the door is always open, and that when and if the time comes, that the opportunity for animosity is always there.”
- “The uncomfortability is the only way that you’re going to be able to grow.”
Let’s Connect!
LinkedIn: https://www.linkedin.com/in/allison-bayley-11881b170/
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