Member Spotlight: Jeremy Rosen and the Next Chapter of Five Star Vacation Home Rentals
- 1 hour ago
- 4 min read
STRASA is at its best when members learn from one another, and Jeremy Rosen is a great example of what real, disciplined growth can look like in the short-term rental industry.
Jeremy started out in a completely different world. He was working full-time as a VA nurse when he began building what became Your Home Away Management. Many of us remember meeting him in those early days, when he was balancing nursing shifts with one or two properties on the side, trying to figure out what was possible.
Jeremy’s “why” sharpened during the uncertainty of the early pandemic.
“Things felt so shaky and unstable,” he told us. “You always hear about having multiple streams of income, and real estate always seems to pop up.”
He was newly married, working in healthcare, and thinking seriously about stability and the future. Short-term rentals became a path forward, not because it was easy, but because it made sense.
From Patient Care to Guest Care
Jeremy also realized quickly that nursing prepared him for hospitality in surprising ways. Hosting guests, he says, is not so different from hosting patients and their families. The work requires constant customer service, attention to detail, and a service-oriented mindset. As he put it, nursing is a profession where you are always bending over trying to help somebody, and that instinct translated naturally into caring for guests.
He began with a rental arbitrage as a strategic way to build his own portfolio and publicly demonstrate what he already knew how to do, applying the systems and standards he had developed while managing his mentor’s property.
The Turning Point: Mentorship and Systems
Like many operators, Jeremy did not scale overnight. In fact, he was stuck at four listings for quite a long time.
The turning point came when he decided he had absorbed all the free information he could through books, podcasts, and nonstop learning, and then made the investment in high-level mentorship.
He joined the Short Term Rental Secrets Mastermind, and he credits that decision with accelerating everything that followed.
“That’s really when everything took off,” he said.
It was not just mindset. Jeremy began professionalizing the business with real systems. One of the biggest changes was building a marketing and automation pipeline that actually brought owners to him. He linked his website to a Google My Business page, connected that to his CRM and calendar, and made it seamless for someone to find him on Google, fill out a form, and land directly on his schedule.
“All someone has to do is find me, fill in a form, and I get the lead sent right to my calendar,” he explained.
At the same time, referrals began to build through relationships with current owners and other operators.
That combination of SEO visibility, automation, and networking helped him grow quickly from 4 to 8 to 12 listings, and eventually to a peak of 22.
Growth With Focus
Another lesson Jeremy emphasizes is focus. Early on, he took what he could get, as most hosts do when starting out. But over time, he became much more intentional about the kinds of homes he wanted in his portfolio. He even offloaded properties that no longer fit, including a duplex and a mid-term rental, because they did not align with the direction of the business.
Interestingly, he notes that letting go of underperforming properties did not hurt revenue. It strengthened the portfolio.
Leaving a Stable Career
By the end of 2025, Jeremy made the leap many hosts think about for years: leaving his VA nursing career to focus on short-term rentals full-time.
“It wasn’t an easy decision,” he said. “You’re told your whole life that a job is stability.”
But over time, he realized that staying in his role was not moving him closer to the long-term freedom and flexibility he wanted for his family. Seeing others in his mastermind successfully make that transition helped him believe it was possible, and the merger created the right opportunity to take the next step.
A Merger and a Bigger Vision
Recently, Jeremy merged his company with his mentor’s business, Five Star Vacation Home Rentals, expanding operations across both San Antonio and the Austin area.
Today, Five Star manages about 65 properties across the two markets. Jeremy leads the San Antonio branch with about 20 properties currently, several more onboarding, and a goal of reaching $2 million in revenue for San Antonio alone this year.
Jeremy’s Advice for STRASA Members
Jeremy’s advice is simple, but not superficial: “Whether you think you can or you think you can’t, you’re right,” he said.
He believes mindset matters because this work is not easy, and you have to push through the hard parts. He also encourages hosts to tell everyone in their network what they are building, because opportunities often come from unexpected places.
In his case, one of his most valuable local assistants came through a decades-old personal connection.
“Tell everybody,” he said. “The universe will conspire in your benefit.”
Jeremy’s approach reflects something STRASA values too: giving first, sharing knowledge, and believing that a rising tide raises all ships. He is the kind of operator who strengthens San Antonio’s hosting community--honest about the learning curve, serious about professionalism, and generous in sharing what worked.
We are proud to have Jeremy, and Five Star Vacation Home Rentals, as part of STRASA, and we look forward to what comes next.
Want to learn more? Reach Jeremy by email here: jeremy@fivestarvacationhomerentals.com or on his websites: