How Hailie Anderson Grew from 57 to 70 Listings Across 3 States with Hostaway

At a glance

• Company: CMHBNB

• CEO: Hailie Anderson

• Founded: September 2022

• Team: 12 members, including virtual assistants

• Portfolio: 70 listings across Tennessee, Utah, and Washington

• Previous platform: Guesty Pro (about 1 year)

• Migration time: 5–7 days, switching from Guesty to Hostaway

• Started with Hostaway: less than 1 year (May 2025)

• Key result: Grew from 57 to 70 listings since switching to Hostaway

• Website: cmhbnb.holidayfuture.com

From 57-Listings to 70-listings, Multi-Market Hospitality Brand

Hailie Anderson’s journey into short-term rentals began in September 2022 after discovering a TikTok video about rental arbitrage—showing how to succeed on Airbnb without owning property. What began from inspiration quickly grew into a 70-listing portfolio operating across Tennessee, Utah, and Washington, supported by a 12-person team, including virtual assistants. Hailie’s approach stands out for its focus on the guest experience, offering personalized communication, video messages, and even car rentals as an upsell through their Airbnbs.

Outgrowing Guesty Pro: The Search for a Scalable Solution

As Hailie’s business grew, the limitations of their previous PMS, Guesty Pro, became clear. Despite a year of use, the software struggled to keep up. Their customer service was lacking, core functions like messaging were unreliable, and the system simply wasn’t built to scale. Hailie realized that if these issues persisted at their current size, future growth of CMHBNB would be impossible.

How CMHBNB Migrated from Guesty to Hostaway in 5–7 Days

When searching for a new PMS, Hailie prioritized finding a company whose team and culture aligned with her own business values. Hostaway stood out not just for its technology, but for its people. Hailie’s first experience with Hostaway was at an event she attended at Hostchella, where she saw firsthand the positive culture and satisfied customers. This sense of partnership and openness to new ideas made Hostaway the clear choice.

The switch from Guesty to Hostaway took just 5 to 7 days. The transition was smooth, with extensive onboarding meetings that gave Hailie’s team confidence before going live. Now, Hostaway powers every aspect of the business—from channel management to cleaning and lock management. The result? The team’s time is freed up, and all tools are centralized, eliminating the need for multiple external solutions.

Before Hostaway vs After Hostaway

Results: Steadily Scaling her Portfolio and Planning for More

Since implementing Hostaway, Hailie grew her portfolio and feels confident about scaling further. She credits Hostaway’s reliability and partnership approach for making this growth possible, stating she wouldn’t even consider expanding if the basics weren’t working seamlessly.

Hailie’s Advice

“Explore your options and find a partner you’re confident you can grow with. No one wants to switch PMSs—choose one that aligns with your goals and supports your vision for the future.”

With plans to continue expanding and optimizing her current operations, Hailie Anderson is just getting started—proving that the right technology partner can make all the difference in scaling a modern hospitality business

Company details

• Name: Hailie Anderson

• Primary markets: Tennessee, Utah, Washington

• Contact: Hailie Anderson

• Direct booking website: cmhbnb.holidayfuture.com

FAQs

Why did CMHBNB switch from Guesty Pro to Hostaway? 

After about a year on Guesty Pro, CMHBNB CEO Hailie Anderson found the platform's customer service lacking, core functions like messaging unreliable, and the system not built to scale with her growing short-term rental portfolio. Those limitations made her realize CMHBNB's future growth would be impossible without a change.

How long did it take CMHBNB to migrate from Guesty to Hostaway? 

The migration from Guesty Pro to Hostaway took just 5 to 7 days. Extensive onboarding meetings gave Hailie's team confidence before going live, and the transition was smooth.

What results has CMHBNB seen since switching to Hostaway? 

CMHBNB has grown from 57 to 70 short-term rental listings across Tennessee, Utah, and Washington in less than a year since switching to Hostaway, with CMHBNB CEO Hailie Anderson crediting Hostaway's centralized platform, reliability, and partnership approach for making that continued growth possible.

What made Hostaway stand out to CMHBNB CEO Hailie Anderson? 

Beyond the technology itself, Hailie Anderson was drawn to Hostaway's team and culture. Anderson first experienced this firsthand at an event at Hostchella, where she saw the company's positive culture and satisfied customers, which gave her confidence in Hostaway as a long-term partner.

What does Hostaway power for CMHBNB day to day? 

Hostaway now powers every aspect of CMHBNB's short-term rental operations, from channel management to cleaning and lock management, replacing the multiple external solutions CMHBNB previously relied on and freeing up its team's time.

What is Hailie Anderson's advice to other property managers considering a PMS switch? 

Hailie Anderson advises exploring your options carefully and choosing a partner you're confident you can grow with, since no one wants to go through a PMS switch more than once. The CMHBNB CEO recommends picking a vacation rental platform that aligns with your goals and supports your long-term vision.