AUGUST 05, 2025
#144 How to Scale Your Short-Term Rental Business Without Burnout
What if you could scale your short-term rental business—without the burnout or chaos? That’s exactly what Kit Leggett did, and in this episode, she’s sharing how.
Kit went from being jobless during COVID to managing 35+ short-term rental properties—all while building a business culture so strong her team calls it their favorite place to work.
But her success isn’t just about numbers.
It’s about how she leads—with intention, with heart, and with the belief that success should feel good.
Why Scaling Your Short-Term Rental Business Can Feel Overwhelming
Growth is exciting—but let’s be honest, it can also feel scary. You’re juggling turnovers, guest issues, and wondering if scaling means sacrificing your freedom. The good news? It doesn’t have to.
Kit Leggett’s story proves you can scale your short-term rental business without losing yourself in the process. She’s done it—and you can too.
Meet Kit Leggett – From Jobless to Managing 35+ Properties
During COVID, Kit faced a major life pivot. After losing her job, she leaned into real estate and discovered short-term rentals. Today, she manages over 35 properties and leads an all-women team that thrives on flexibility, fun, and family. They even bring their kids to team meetings and celebrate wins with zip-lining adventures.
The Secret to Scaling with Soul
Scaling isn’t just about adding more properties—it’s about building a foundation that supports you and your team. Kit calls this “scaling with soul.”
Systems That Simplify
She built documented workflows for cleanings, turnovers, and guest communication, using tools like property management software and automation to save time.
A Culture That Inspires
Kit created a supportive environment where her team feels valued, motivated, and excited to contribute to the bigger vision.
Mindset That Fuels Growth
The biggest shift? Believing that growth doesn’t mean chaos—it means possibility.
Tools and Strategies to Scale Your Short-Term Rental Business
Want to follow Kit’s lead? Start with these essentials:
- Property management software for automation and pricing adjustments
- Documented systems (Loom videos, Google Docs) for training and onboarding
- A willingness to delegate—even if it’s scary at first
3 Simple Steps to Start Scaling Today
1. Systemize Your Workflows
Record how you handle cleanings, guest messaging, and turnover days. These become your training manuals for future hires.
2. Make One Smart Hire
Pinpoint your biggest bottleneck and delegate it. Even hiring a part-time VA or local assistant can free up hours every week.
3. Lead with Your Values
Define what you want your company to feel like—family-focused, fun, flexible—and bake it into every process.
Ready to Scale Without Burnout?
Kit Leggett proves you don’t have to hustle your way into exhaustion to grow a successful short-term rental business. With the right systems, mindset, and team culture, you can scale—and actually love your life more as you grow.
HIGHLIGHTS AND KEY POINTS:
[00:05] A short introduction about our guest Kit Leggett and what made her decide to start in the world of short-term rentals
[04:19] Kit shares what sparked her first STR listing during COVID, jumpstarting her journey in a booming market
[06:13] Kit recounts the emotional toll of doing everything herself early on, leading to a breakdown that pushed her to finally ask for help
[09:44] Kit shares the messy but meaningful evolution from micromanaging her first cleaner to creating a more sustainable, trust-based system
[11:15] How hiring a local, all-women team transformed Kit’s business and became a mission-driven extension of her values
[13:33] Kit shares her client reactions and the day-to-day logistics of working with kids
[16:16] What inspired Kim to create a work culture where kids are welcome
[18:55] How Kit’s team-first mindset and hands-on leadership organically created a loyal, supportive culture among her all-women staff
[24:23] Kit describes how she plans team activities organically and affordably, focusing on connection rather than formal budgets
[27:48] Kit shares how a casual coffee chat led to acquiring 13 hosting contracts through an informal but strategic business offer
[31:07] How Kit calculated a fair purchase price for hosting contracts using a practical, grounded approach
[33:52] Kit reveals how she financed her contract acquisition that did not require upfront cash
[35:38] Kit shares the single biggest factor enabling her to manage over 35 properties
[38:12] Kit’s perception of failure and her response to setbacks
[39:44] Kit reveals a game-changer software for automating operations and managing cleanings at scale
[42:22] How Kit structures scheduling and autonomy for her cleaning team
[44:32] Kit shares about her plan to expand beyond her local market
[47:02] The lightning round
Golden Nuggets:
- “When we find good team members, they’re like gold to our businesses, and we want to do everything we can to keep them.”
- “I just love supporting women, and we’re a tight knit group, and we really rely on each other, and help each other.”
- “Any kind of culture starts at the top, and works its way down.”
- “When your team knows that you will bend over backwards to help them, they will do the same for you.”
- “It’s so important to test different things on the journey of continuous improvement. But give yourself grace when it doesn’t work out and you have to pivot, that’s okay.”
- “The cleaners are the backbone of the business. And if you don’t have a good team or good systems in place with good software, then you’re going to be scrambling.”
- “Surround yourself with people that do encourage you and do help you.”
Let’s Connect!
Website: https://stayinthevalley.com
Instagram: https://www.instagram.com/stayinthevalley/
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