Naples Vacation Properties Reshapes the Luxury Rental Market

Source: Naples Vacation Properties

Reported By: Matthew Kennedy

In the competitive world of luxury vacation rentals, it’s rare for a newcomer to gain significant market share in just a few years. Yet Naples Vacation Properties, founded by brothers Jake and Keith Ponsler, now commands over 25% of all vacation rental search traffic in Naples, Florida—placing them firmly among the top three operators in the region and setting the stage for national growth.

The company’s origin story began with frustration. While building their own high-end rental portfolio in Naples, the Ponslers found the local property management options lacking—outdated systems, minimal transparency, and a service model that left both owners and guests underwhelmed.

As licensed real estate brokers, they saw an opportunity. Initially, they began managing a select group of properties for clients who had purchased investment homes through their brokerage. Demand quickly outpaced expectations, with word-of-mouth and measurable results fueling rapid growth.

Today, the company manages more than 100 luxury vacation rentals across some of Naples’ most sought-after communities, including Treviso Bay, Park Shore, and Pelican Bay. The Ponslers’ approach blends high-touch service with a technology-driven backend, creating efficiencies that benefit both property owners and guests.

This tech-forward model, paired with meticulous property presentation and responsive guest support, has been key to their success.

One of the company’s most strategic achievements has been its digital reach. Capturing more than 25% of all vacation rental search traffic in Naples means that one in four prospective guests searching online lands on their platform. It’s a figure that reflects not only strong brand positioning but also savvy digital marketing, SEO optimization, and targeted outreach.

Their next target? Achieving a 50% share of the Naples vacation rental search market while using the same operational playbook to enter other premium destinations across the U.S.

The groundwork is already being laid for expansion into other high-demand vacation markets, from coastal retreats to luxury resort communities. The brothers’ vision is to build the most respected vacation rental brand in every market they enter, replicating the efficiency, service, and trust that have fueled their rise in Naples.

For property owners, this means access to a proven system that maximizes revenue while safeguarding the guest experience. For travelers, it ensures consistent quality, whether they’re booking a waterfront estate in Florida or a mountain lodge in another exclusive destination.