#121: The Business of Big Short-Term Rentals: Kim Herrlein’s Secrets

by | Feb 25, 2025 | Podcast

Big Short-Term Rentals

FEBRUARY 18, 2025

#121: The Business of Big Short-Term Rentals: Kim Herrlein’s Secrets

Scaling and Managing Large Vacation Rentals Like a Pro

Ever wondered what it takes to scale and manage large vacation rentals successfully? In this episode, I sit down with Kim Herrlein, a real estate investor who has mastered the art of hosting large groups and turning big properties into thriving short-term rentals.

Kim shares the strategies that helped her expand her portfolio, from acquiring and designing properties that cater to large groups to optimizing operations for efficiency. She dives into the challenges of managing high-occupancy rentals, keeping guest experiences seamless, and ensuring top-tier cleanliness despite high turnover. Plus, she reveals her secrets to building a loyal customer base and staying ahead in the competitive vacation rental market.

If you’re looking to scale your short-term rental business or break into large-group hosting, Kim’s insights will give you the tools and inspiration to take your rentals to the next level. Don’t miss this expert-packed conversation!

Why Large-Scale STR Management Matters

As the short-term rental industry grows, catering to larger groups presents unique opportunities and challenges. Kim highlights key factors that make large vacation rentals successful, including:

  • Maximizing Space: Expanding and designing properties to accommodate more guests.
  • Guest Experience: How to create seamless, high-quality stays.
  • Scaling Operations: Managing multiple properties while maintaining high standards.
  • Market Timing: Understanding when to sell and reinvest in properties.

Key Takeaways

[00:09] A short introduction about our guest Kim Herrlein

[00:56] How Kim started in short-term rental industry and scaling her first property

[01:44] Kim shares the planning and renovation of expanding a four-bedroom house into 10 bedrooms

[03:09] Kim explains how personal experience and a prime Coachella location drove her investment decision

[04:16] How Kim gradually expanded a four-bedroom home to 10 to maximize its rental potential

[05:58] Kim shares how she expanded to 14 properties across five regions, adapting designs and learning how guest needs differ by location

[08:14] Kim highlights the importance of market timing to sell properties at their peak value

[11:19] Kim talks about new owners’ unrealistic expectations, the evolution of property management, and using tech and VAs to stay ahead

[15:48] How Kim manages and overcomes the challenges of managing large vacation properties

[21:55] Kim talks about the challenges of turnovers for large vacation rental properties and maintaining cleaning standards

[25:06] What Kim looks for when hiring a host and the qualities and systems she values to ensure a great guest experience

[28:36] How Kim manages guest communications for large groups to ensure a seamless experience

[31:57] Kim talks about the challenges of securing repeat bookings for large-group vacation rentals

[35:12] Kim highlights the biggest lesson she has learned in hosting large groups of people

[37:48] The lightning round

Golden Nuggets

  • “Inheriting property management clients can be challenging because they often lack market exposure and understanding.”
  • “Having the right team and systems in place is crucial. I couldn’t do this without my people and tech.”
  • “Guests don’t mind issues as much as they mind issues being ignored. Communication is everything.”
  • “This too shall pass. Stay in gratitude, whether times are tough or great.”

Take Your STR Business to the Next Level

Whether you’re new to short-term rentals or looking to scale your business, Kim’s expertise offers a roadmap for success. From maximizing space and guest experience to scaling efficiently, her strategies will help you stay competitive in the growing STR market.

Ready to transform your vacation rental business? Tune in now!

Let’s Connect!

Website: Purveyors of Leisure

Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

The Latest…

#156  Unreasonable Hospitality with Candice Menard

#156 Unreasonable Hospitality with Candice Menard

OCTOBER 28, 2025  #156  Unreasonable Hospitality: How Candice Menard Is Transforming the Short-Term Rental ExperienceWhat if standing out in the short-term rental industry isn’t just about the property—but the experience you create? In a world where guests are flooded...

#155 Ashley Freeman’s Short-Term Rental Success

#155 Ashley Freeman’s Short-Term Rental Success

OCTOBER 21, 2025  #155  Short-Term Rental Success: How Ashley Freeman Built a 115-Property EmpireHow do you rebuild your life—and create extraordinary success—after everything falls apart? In this episode, I sit down with Ashley Freeman, a former tennis pro who turned...

#154 Building Wealth Through Short-Term Rentals

#154 Building Wealth Through Short-Term Rentals

OCTOBER 14, 2025  #154  Building Wealth Through Short-Term Rentals: How Zoey Berghoff Turned a Tiny Dome Into a Real Estate EmpireCould a 300-square-foot glamping dome really be the start of a real estate empire? For Zoey Berghoff, the answer is a resounding yes. In...

#153 Abundance Mindset for STR Growth

#153 Abundance Mindset for STR Growth

OCTOBER 07, 2025  #153 Abundance Mindset for STR Growth: Mindset Shifts That Boost Your RevenueWhat if the biggest barrier to growing your short-term rental business isn’t strategy, listings, or even money—but your mindset? That’s exactly the lesson Esmeralda Alba...