By Avah Taylor

Jamaica’s tourism economy is undergoing a transformation, and Different Properties Limited isn’t just adapting to the change; it’s helping lead it.

As the island’s short-term rental (STR) market grows and regulatory discussions intensify, developer Gary Matalon is introducing an innovative model that could redefine the entire category.

Through Different, Matalon and his partners are introducing a new framework: professionally operated, fully registered, branded properties that leverage the short-term rental model but defy the “Airbnb” stereotype.

“Short-term doesn’t mean short-sighted,” Matalon said in an interview. “We’re building for people, and for the long game.”

Public discourse often conflates all STRs with Airbnb, but as Matalon notes, Airbnb is merely a platform, not a property type. “We have all-inclusive, fully licensed hotels in Jamaica that list rooms on Airbnb,” he explains. “It’s just a booking tool, like Expedia or Hotels.com.”

This clarity extends to their unique position in Jamaica’s heated STR debate. Where established hotels and casual STR operators clash over regulatory fairness, Different sidesteps the conflict entirely with a hybrid model: a scalable, professionally managed alternative that is compliant like a hotel, yet functions as a streamlined, limited-service stay, without daily housekeeping or room service, just consistency and control.

“Some people feel like we’re trying to avoid the regulations other hotel players are subject to,” Matalon says. “But that’s not the case at all. We’re going to be a fully licensed and regulated hotel, just with a different operating model.”

The company’s innovation lies in its dual structure. On the development side, Different builds and sells units to investors at accessible price points. Each unit is then leased back and operated under centralised, hotel-grade management, removing the day-to-day burden from owners while preserving a consistent guest experience.

This is hospitality reimagined for today’s market: investors gain access to the Caribbean’s top-performing real estate asset class without operational headaches, simultaneously allowing guests to enjoy the freedom of short-term rentals with the confidence of a fully compliant, professionally managed stay.

“A lot of the listings out there are hit or miss,” Matalon tells Our Today. “STRs aren’t a set-it-and-forget-it kind of investment. They’re a real hospitality business, and not everyone is treating them that way.”

Far from being a reaction to regulatory pressures, Matalon clarifies that their approach was strategic from day one. “We saw the writing on the wall,” he says. “This was designed from the ground up as a fully compliant, limited-service hospitality brand.”

But the real driver? Access. Although hospitality real estate has traditionally been elite-dominated, Different opens the asset class without compromising standards. “We wanted to create a credible investment vehicle that expands access while also raising the bar.”

Unlike traditional hotels or all-inclusive resorts, Different is designed to enable a more flexible model. It supports guest-facing brands and gives investors the structure, scalability, and long-term value they’re looking for.

“We’re creating something more in tune with how people want to travel and invest today,” Matalon states. “And we’re doing it through the lens of authentic design, local culture, and smart operations.”

Every project is developed and managed in-house by a founding team with deep expertise in real estate, governance, hospitality, and finance, including Christopher Williams, Michael McMorris, Deighton Levee, and Armando Pizzuti.

At the helm is chairman Christopher Williams, whose track record includes building one of the Caribbean’s most successful investment banks and leading regional giants through major growth phases. His financial acumen and marketing instincts bring a rare balance of risk and innovation. 

Michael McMorris provides the governance compass, shaped by his experience chairing institutions like VM Group and JAMPRO. Execution is led by Deighton Levee, a mechanical engineer and head of Jamaica’s top project management firm, ensuring precision from planning to completion. And Armando Pizzuti bridges vision and operations, drawing on decades in Caribbean hospitality to align strategy with delivery.

“Everyone leads where they’re strongest,” Matalon says. “That’s what makes Different… different.”

Amid evolving STR regulations, Matalon’s stance is clear: Different isn’t exploiting loopholes, it’s shaping the future of the category.

“We’re embracing compliance, not avoiding it. Our model includes industry best practices: Safety standards, full tax reporting, JTB registration, and JHTA membership. This aligns with where Jamaica is headed: more transparency, better regulation, and smarter investment.”

“We believe structure builds trust,” he shares. “And trust attracts capital, from investors and from the guests we serve.”

In a sector often defined by tension between hotels and independent STRs, Different Properties is quietly forging a third lane: transparent, compliant, and built for longevity.