Largest Hawaii Vacation Rental Company Faces Major Shake Up

When travelers booked with Hawaii’s largest vacation rental operator, many expected paradise. Instead, they were met with last-minute cancellations that left them scrambling, properties that had not been cleaned since the prior guest, or bills padded with fees that doubled the nightly rate. Complaints like these accumulated for years, leaving Vacasa with some of the lowest ratings in the industry and a damaged reputation in Hawaii.

Now that failed model is being dismantled. Vacasa has been acquired by Arizona-based Casago, which is transitioning to a new franchise system that empowers local operators rather than relying on distant mainland call centers.

From failed mainland control to local ownership.

Vacasa ran everything from far-off corporate offices, managing thousands of homes from Portland or Boise as if Maui, Kauai, or Oahu were interchangeable with them. Technology may have been slick, but the aloha spirit was often missing. Beat of Hawaii readers described misleading listings, lack of local support, and exorbitant fees. A 1.7-star average Google review score told the very same story.

Casago is betting that the way forward is the opposite approach, and it may be right. Its franchise model empowers operators who live on the islands, know the communities, and have a vested interest in the success of the business. In theory, this simultaneously creates accountability and a more personal service experience, which Vacasa has mostly lacked.

What this means for Hawaii homeowners.

For Hawaii vacation rental homeowners, Vacasa was once a tempting partner. It promised exposure, high-tech booking infrastructure, and professional cleaning services. But as the company grew, trust started to fray. Many owners switched back to smaller local managers, often reporting higher earnings and far more peace of mind.

The franchise model could change that again. If Casago installs capable Hawaii operators, owners may finally get the best of both worlds. That means local, accountable management that can meet face-to-face, alongside national marketing and technology that can keep calendars full.

Success, however, will depend on the quality of the franchisees Casago can recruit. A strong local team on Maui or the Big Island could rebuild confidence. A weak one could leave homeowners facing similar frustrations to those they had with Vacasa, just under a new name.

What visitors may notice.

At its peak, Vacasa managed over 1,100 Hawaii vacation rentals. By early 2024 that number appeared to have dropped to 886, and today a website property search we performed revealed only about 300 live listings. That steep decline in availability, combined with a reputation for uneven service, left many travelers frustrated and wary of booking.

Casago’s upcoming shift to a franchise model could change the experience. Local operators are directly accountable to their communities, which can result in faster responses, cleaner properties, more accurate listings, and potentially friendlier pricing if franchisees compete with independent managers.

Still, there is a major unknown. Until Casago’s Hawaii system is thoroughly tested, variations in franchisee quality may mean the experience remains uneven.

Under pressure from Hawaii regulations.

Hawaii’s counties have become the front line in the battle over short-term rentals. Maui is attempting to phase out thousands of units, Oahu has imposed a 30-day minimum when the 90-day one failed, and Kauai continues to enforce strict zoning and other restrictions. All of it is driven by housing shortages and the disruption vacation rentals bring to neighborhoods.

Large mainland operators, such as Vacasa, often struggled to keep pace. With decision-makers thousands of miles away, their responses to local rules felt slow and sometimes tone-deaf. Casago’s franchise approach, if it delivers real island-based operators, could give the company a leg up.

Local managers are far more likely to understand county rules, maintain permits, and adjust quickly when laws change. That may help steady Hawaii’s vacation rental market at a time of intense political and community pressure.

A Vacasa collapse and a possible comeback.

Not long ago, Vacasa was the travel darling of Wall Street. Investors poured billions into the Portland-based startup, betting it would become the Airbnb of professionally managed vacation rentals. When Vacasa went public in late 2021, it was valued at more than $4 billion and touted as a tech-driven solution that would bring order to the fragmented vacation rental industry, which is mostly comprised of independent managers. Analysts discussed explosive growth, and independent Hawaii vacation rental managers shuddered as the company rapidly expanded into markets, including Hawaii.

But the promise unraveled as quickly as it arrived. By 2024, Vacasa’s value had plummeted 97 percent to only 128 million. Shareholders were left with pennies, homeowners defected, and thousands of properties went into limbo. The same scale and speed that first fueled Vacasa’s rise also set the stage for its precipitous fall, with customer service complaints and a myriad of challenges piling up.

Casago stepped in earlier this year, acquiring Vacasa and promising a very different path. Shifting to a franchise model is not a minor adjustment. It is an admission that Vacasa’s original strategy failed, and it hit especially hard in Hawaii.

What Beat of Hawaii readers told us.

When we previously covered Vacasa’s decline, readers were blunt. Nancy L. said her last Vacasa stay on Maui was nothing like the photos, describing it as overpriced and under-maintained. Paul K. commented that Vacasa was too big to care about the details that matter in Hawaii. Homeowner David B. told us he switched to a local broker after years with Vacasa and that it has been far better in every way.

Those sentiments point to why Casago is now trying a different approach. By shifting control to local operators, the company aims to address exactly where Vacasa stumbled.

The open questions for Vacasa Hawaii.

There are still major uncertainties about what happens next.

• The first is who will run Casago’s Hawaii franchises, since the quality of the operators will make or break this experiment.
• Another question is whether fees will drop, as travelers and owners alike have long complained about Vacasa’s layers of charges, and franchisees may have more leeway to simplify those.
• It also remains to be seen how local managers will compete, as Hawaii’s independent vacation rental firms rebounded during Vacasa’s stumble and may or may not hold their ground against a franchised giant with national marketing and technology prowess.
• Finally, regulators will have a say. Counties like Maui may still consider cutting thousands of rentals, regardless of who manages them, which means a new business model does not eliminate that pressure.

Where do Hawaii vacation rentals go from here?

Hawaii’s once biggest vacation rental company is being remade from the inside out. Vacasa’s experiment with centralized, high-tech management left many homeowners and visitors disappointed, ultimately destroying their business. Casago’s franchise model is a calculated bet that local control, accountability, and knowledge can win back lost trust.

For Hawaii vacation rentals, this could be another turning point. Either franchising provides visitors with a better stay and homeowners with a steadier hand, or it becomes just another failed chapter in the long saga of Vacasa Hawaii vacation rentals.

Have you rented from Vacasa and would you do so again? Please comment on today’s post.

Lead Photo Credit: Montage Kapalua Bay, Maui.