NOVEMBER 25, 2025
#160 How to Build a Boutique Short-Term Rental Business Without Burnout
Ever feel like scaling your short-term rental business means sacrificing your sanity? You’re not alone. Many hosts think success only comes by adding more properties, working longer hours, and constantly firefighting. But Jessica Hill, founder of Jet Setter Property Management, is proof that you can grow a profitable STR business without burning out.
Jessica’s boutique approach—12 carefully curated properties—shows that doing less, but doing it well, can create more revenue, happier guests, and a business that actually fits your life. In this episode, she shares exactly how she’s built a system that balances passion, profit, and purpose.
Intentional Design That Drives Connection
One of Jessica’s secrets? Boutique, emotionally resonant design. Every property is intentionally crafted to create a guest experience that sticks. Think custom murals, carefully selected decor, and curated amenities.
“I design spaces that make people feel something,” Jessica says. “When guests connect emotionally, they return—and they tell their friends.”
Boutique properties don’t just look good—they perform better. Emotional connection drives repeat bookings, five-star reviews, and higher nightly rates. For small portfolios, this is a major growth lever without adding doors or stress.
Systems, Boundaries, and Sustainable Growth
Jessica’s approach isn’t just about design—it’s about systems and boundaries that prevent burnout. She balances her healthcare career, motherhood, and business by:
- Delegating tasks to a trusted team of cleaners, virtual assistants, and local partners
- Automating guest communication with property management software
- Setting clear operating procedures that keep her properties running smoothly
- Protecting personal time so she can focus on high-impact activities
By focusing on sustainable systems instead of relentless hustle, Jessica has built a business that generates revenue without running her into the ground.
Boutique STRs: Quality Over Quantity
Scaling isn’t always about adding more properties. Jessica’s 12-property portfolio outperforms larger portfolios because each property is highly optimized for guest experience and profitability.
She advises:
- Focus on fewer, better properties
- Create unique experiences that guests can’t forget
- Standardize operations to save time and reduce stress
- Align your business model with your lifestyle goals
The boutique approach allows for more control, less burnout, and greater profitability per property.
Leading an STR Business on Your Terms
Jessica’s story is a blueprint for anyone craving freedom and impact in their STR business. She proves that profit and purpose can coexist, that growth doesn’t have to equal exhaustion, and that intentionality is the secret to scaling sustainably.
“More isn’t the goal—meaning is,” Jessica says. And her business reflects exactly that.
For hosts tired of chasing size over quality, her approach is a reminder that you can build a profitable STR business that supports your life and makes a difference for your guests.
Tune in now to hear Jessica Hill share her boutique STR model, her systems for balance, and her insights on scaling without burnout.
HIGHLIGHTS AND KEY POINTS:
[00:56] A short introduction about our guest Jessica Hill and how she got into the world of short-term rentals
[03:32] Jessica talks about her company and explains why she intentionally operates a boutique, hands-on property management model instead of scaling into a large, volume-driven portfolio
[05:19] Jessica emphasizes the importance of intimate, hands-on management that boutique operators provide compared to large-scale property managers
[09:55] Jessica’s active involvement in the guest experience and daily operations despite having a team
[11:03] Jessica shares about her W-2 job and what she has pulled over from her W-2 into her short term rental business
[12:35] Jessica explains explains why strategic design is a performance lever, not just aesthetics, in driving bookings and brand demand
[16:11] Jessica talks about how she monetizes design and listing optimization as value-add services within her boutique hosting model
[17:31] Jessica shares the key foundations smaller hosts should prioritize to deliver a high-touch guest experience through a boutique-style approach
[20:11] How Jessica balances a full-time W2 career, motherhood to a special needs child, and her co-hosting business through intentional time management
[22:32] Jessica shares how motherhood shaped her communication philosophy in short-term rentals
[25:15] Jessica emphasizes the power of over-communicating with her team to build ownership and brand-aligned service
[27:27] Jessica shares her piece of advice for all women who are chasing big dreams while also navigating life, being a mom, working a full time job
[29:51] The lightning round
Golden Nuggets:
- “Start and make sure that you have the proper systems in place.”
- “I have brought those people on my team to help with those things, so that way I can be a more effective property manager and do the things that I love to do.”
- “When you love what you do, you never work a day in your life.”
- “Don’t lose yourself in the day to day of motherhood. Carve out a little time for yourself, because you can’t pour from an empty cup.”
- “When we do learn something, it’s important that we implement it and execute it and keep our business moving forward.
Let’s Connect!
Website: https://stayjetsetting.com/
Facebook: https://www.facebook.com/stayjetsetting
Instagram: https://www.instagram.com/stayjetsetting
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