Scaling 3 to 29 properties in 2 years with a powerful tech stack
Ryan Ramona turned a small portfolio of three vacation homes into a fast-growing short-term rental management business, Ramona Rentals, which now operates 29 properties.
- Location: Central Oregon, USA
- Number of listings: 29
- Years using Hostfully: 2
- Favorite features: Integrations (PriceLabs, Stripe, Breezeway, RemoteLock), automation tools, channel manager, and centralized property management
Overview
Before
- Managed all operations manually across several disconnected tools
- Limited automation for pricing, guest communication, and accounting
- Relied on third-party cleaners and contractors, leading to inconsistent results and higher costs
After
- Centralized property data, communication, and integrations
- Automated pricing, payments, and operations through Hostfully’s ecosystem
- Reduced cleaning costs by bringing 75% of cleans in-house
Impact
- Scaled from 3 to 29 properties in just two years
- Achieved higher guest satisfaction and operational consistency; preparing for next stage of growth through integrated accounting with Clearing
- Built a sustainable staffing model with 2 full-time employees, 5 seasonal cleaners, and a remote assistant
“Hostfully became the backbone of our tech stack. It connects everything—pricing, cleaning, locks, payments—and gives me one place to monitor the entire business.”
Ryan Ramona, Ramona Rentals
Before
When Ryan Ramona started managing his first few short-term rental properties, his operations were simple, but time-consuming. Guest messages came through multiple booking platforms, cleaners were hard to coordinate, and payments were handled manually.
As Ramona Rentals emerged as a professional vacation rental company, Ryan realized he was spending huge parts of his day driving to properties an hour away for small fixes, and troubleshooting check-ins, rather than improving the guest experience or finding new properties. He needed a system that could connect every part of the operation. “I knew the PMS was going to be the central hub to everything. When I was researching property management softwares (PMSs), Hostfully kept coming up as an integrations’ leader. That was the type of company I wanted to grow the ecosphere around.”
After
Between its robust integrations, streamlined systems, and coordinated automations, “Hostfully became the backbone of our tech stack,” says Ryan. “It connects everything: pricing, cleaning, locks, payments. And it gives me one place to monitor the entire business.”
With Hostfully as the foundation, Ryan lists across Airbnb, Vrbo, Google, and his own direct booking site, and utilizes a range of integrations, including:
- PriceLabs for dynamic pricing, ensuring each property earns optimal revenue year-round
- Stripe for automated and secure payments
- Breezeway for task management and cleaner coordination
- RemoteLock for guest access and property safety
- Truvi for damage protection
These integrations allowed Ryan to automate recurring workflows before expanding his team, helping him stay lean while maintaining quality. “I wanted systems that could handle growth before I hired more people. That’s exactly what Hostfully and its integrations let me do.”
But perhaps most notable among Ramona Rentals’ tech stack was Ryan’s prescient adaptation of bookkeeping software. Once he added properties other than his own, he switched from using a professional accountant to integrating trust accounting software.
Ryan emphasizes the importance of proper bookkeeping systems for successful and seamless STR scalability. “Mistakes in accounting can cause so much more downstream problems.” Ryan explains. “Prioritizing my chart of accounts, making sure things are correct early on in accounting, has given me the availability to scale a little faster. Because if my accounting was messed up that would probably mean I was having some cash flow issues, which would be a big problem for scaling.“
As the business continues to scale, Ryan plans to enhance his financial reporting capabilities even more with the help of additional integrations.
While Ryan knew early on that having his finances in order was critical, he waited awhile before bringing on additional staff. By shifting from available contractors to five in-house cleaners, and hiring several additional team members to help with operations, Ryan has been able to expand his business even further.
With Hostfully’s PMS, Ryan can assign jobs to his in-house team members, and receive notifications of job updates. The result is improved reliability and reduced expenses. Today, 75% of Ramona Rentals’ cleanings are performed by employees—a decision that not only cut costs, but also strengthened accountability and guest satisfaction. His goal is to hit 100% in-house cleaners in the near future.
In just two years, Ramona Rentals went from a handful of homes to a thriving portfolio of nearly 30 properties. Ryan attributes this achievement in large part to his early investment in Hostfully’s PMS, an integrated tech stack, and the vacation rental company’s new hires.
“I’ve been able to step away from the day-to-day minutiae to focus more on growth and managing a team,” Ryan shares. With four new properties in the immediate pipeline, Ryan prepares to expand his footprint even further: “It’s the start of an exciting new chapter for the business.”
