Arizona Tribune - Naples Brothers Build Vacation Rental Powerhouse, Disrupting a Decades-Old Industry

NAPLES, FLORIDA / ACCESS Newswire / August 6, 2025 / What began as a personal investment journey for brothers Jake and Keith Ponsler has quickly grown into one of the fastest-scaling vacation rental and real estate brokerages in Southwest Florida. Naples Vacation Properties, now a top-three operator in the region, is on an aggressive path to dominate the local market and expand nationally.

Frustrated by the limited and outdated property management options available while building their own rental portfolio in Naples, Jake and Keith set out to build something better. As licensed real estate brokers, they initially took on a handful of properties for clients who had purchased investment homes through their brokerage-and who shared similar dissatisfaction with the status quo.

Early success snowballed. Leveraging their sales background, tech-savvy operations, and a relentless focus on guest and owner experience, the brothers grew Naples Vacation Properties into a market-leading operation managing over 100 high-end vacation rentals across top communities like Treviso Bay, Park Shore, and Pelican Bay.

"We knew there had to be a better way to do this-smarter systems, better communication, more transparency. So we built it," said Jake Ponsler, co-founder.

Today, Naples Vacation Properties owns over 25% of all vacation rental search traffic in the Naples area, meaning 1 in 4 online rental seekers end up on their site. Their ambitious goal? Reach 50% market share and expand into other tourist-heavy regions across the U.S. using a proven operational playbook.

"Our growth wasn't luck," adds Keith Ponsler. "We've built a scalable backend, assembled a top-tier team, and we constantly refine our systems. That's why we've been able to outperform operators who've been in this business for decades-within just a few years."

With robust technology, in-house expertise, and a loyal client base of property owners and travelers, the company is already laying groundwork in other premium vacation markets. Their aim is clear: to become the largest, most respected vacation rental brand in each market they enter-starting with Naples.

SOURCE: Naples Vacation Properties

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A.Anderson--AT