Maintaining Owner Trust and Retention in a Slower Market

Hal Conick
3/30/2026

Steve Schwab visited Puerto Peñasco, Mexico, for a relaxing stay. It turned into a new business and multiple decades of relationships with homeowners.

It all started after leaving the U.S. Army, when Schwab wanted to hang out seaside to decompress. There, he met Bruce, an older man who owned a small beach home company. Bruce wasn’t feeling so well, so Schwab helped him with the maintenance and upkeep of the properties he managed. They became friends.

After Bruce died, his wife asked Schwab if he wanted to buy the company—her husband spoke highly of him. Schwab looked through the company’s financial papers and saw that it made more in the past year than he had made in his entire life. On January 1, 2001, he bought out the company, with some help from Bruce’s wife. She handed him $100,000 in money orders and papers with the phone numbers of the 16 owners whose properties the company managed.

Schwab sat in an office, staring at the stack of paper that was his new business. “There was no system,” says Schwab, now CEO of vacation rental company Casago. “I didn’t even have their addresses. She said she’d be back after lunch, and I never saw her again. That was my first day of property management.”

The first weeks and months were trial by fire, but Schwab decided to approach his new job by being honest with homeowners. He called each one and told them the truth: “I have no idea what I’m doing, but if I mess it up, I’ll make it right.”

While there were bumps along the way—including one home having all its contents stolen by a guest—Schwab didn’t lose a single owner. Within a couple of years, the 16 owners under management turned into 30, which turned into Casago managing 3,000 properties across 70 markets. In 2025, its success turned into a multimillion-dollar merger with Vacasa.

While he’s had moments where he was unsure the business would survive, Schwab has maintained relationships with owners through honesty and proactivity. “It ties to the four factors of trust—integrity, reliability, intention, and competence,” Schwab says. “In each one of those, you can be stronger or weaker, but they all have to be part of the formula. When you’ve gone through something hard with your homeowners, it creates a sense of trust with them.”

The current market may be a trust-building moment for vacation property managers, as the post-pandemic boom has slowed. According to a Redfin report, demand for vacation homes fell to a six-year low in 2024, as homebuyers took out far fewer mortgages than in previous years. In 2024, homebuyers took out 5% fewer mortgages than in 2023 and a whopping 66.5% fewer than from the high point in 2021.

Demand is falling fastest in Florida, Redfin reports, a vacation rental hotspot—vacation home mortgages dropped 32.2% in Miami in 2024, for example. Some of the reasons given for the lower demand, according to Redfin’s analysis, are rising costs of all housing, a cooling rental market, and the return of office work.

And the market does matter, according to Annie Holcomb, owner and chief strategist of vacation rental consultant Annie & Company. Property managers must know trends in market entrants, but also the economy, how often people are traveling, and what nearby events are drawing in travelers. Instead of managers leaving listings on Airbnb and hoping for the best, she says that down markets can be an opportunity to be proactive with the business, build out direct bookings, and become an even stronger brand.

“It’s a slow build,” Holcomb says. “It’s constant participation and constant engagement. You have to really understand all the things that are happening, not just in your market, but in the industry. And you have to participate in it.” The market isn’t all bad news for owners and property managers. In AirDNA’s 2025 midyear report, it shares that demand for vacation rentals is still growing, creating stronger pricing power for extant owners and managers. And there are other ways for hosts to continue to see success, including creating a unique experience, better interior design, and, as Holcomb mentions, building out direct bookings.

“The top performers are usually doing well in a tough market,” says Dennis Goedheid, owner of vacation rental company Casiola. “Where you see the biggest losers is the bottom of the market, the properties that have not been updated. They see their occupancy drop significantly and may have to drop the rate.”

Market conditions don’t have to lead to a brutal conversation with owners, as property managers who have prepared can succeed through even the toughest times.

Set Owner Expectations Early

When Goedheid entered the industry, he acquired 20 homes located in one area. The owners and guests were king, as far as he was concerned, and he’d acquire new owners no matter what demands they had. It was a discovery phase for him in the vacation rental world, he says, one that many managers experience—and one that, for him, led to headaches.

“You try to do your best,” Goedheid says. “But for some people, your best is not enough, and they always want more. And if you give them a hand, they’re going to take an arm.”

Now, Goedheid says that Casiola approaches relationships with owners differently. From the start, it actively monitors for red flags by introducing its management program to potential owners. The home will be managed a certain way, no exceptions, with quality, safety, and cleanliness top of mind, alongside generating high revenue. If a potential owner doesn’t like the program, they aren’t a good fit.

While this may sound negative, Goedheid says that it’s been a way to make business scalable. Not every owner wants to join a large company in multiple destinations, and that’s OK. Setting expectations from the start makes it easy for both sides to figure out if it’s a good cultural fit.

When Holcomb managed properties, she knew that both setting and learning owner expectations was an essential step. A self-described conflict avoider, Holcomb learned that being proactive in setting and learning expectations meant less conflict in the relationship, not more. “You should know how they’re going to interact with you within the first few conversations, before they ever sign a contract,” Holcomb says.

Onboarding is where every tough conversation begins, Schwab says. Like Goedheid, his company has a booklet it gives to owners for homeowners looking to join, which sets expectations on responsibilities, expectations from guests, revenue management, and why rates may change throughout the year, among other topics.

“The ground rules in the beginning are how you build long-term relationships,” Schwab says.

Meeting the Moment

Amid difficult moments with owners—whether market conditions or a service error—Schwab remembers the “service recovery paradox.” Successfully recovering from faulty service, according to this paradox, increases customer confidence in a business, more so than if a bad moment had never happened.

“Having an imperfection in your system where you have to come in and restore the relationship actually builds affection,” Schwab says. “Correcting mistakes can be your opportunity to build relationships.”

If bookings are down, for example, it’s best to simply face the conversation head-on by reaching out to owners, Holcomb says. Property managers can discuss the next steps with owners and hear out their concerns. Sometimes, owners often simply want to be heard.

“They’re frustrated because maybe they weren’t able to refinance their mortgage, or maybe it went up because they had a balloon payment, and they weren’t prepared for that,” Holcomb says. “They’re often panicking about something completely unrelated to the way you service them.”

If property managers fail to carve out regular time to communicate with owners, Holcomb says they may start talking to other property owners about perceived shortcomings in service. Even with regular interactions with owners, this may happen. When it does, Holcomb suggests hearing owners out, then letting them know that you’ll investigate what information they’ve reported and following up with them soon after.

“It gives you a clear ability to research, understand, and digest what they’ve said and not get into a back-and-forth,” Holcomb says, allowing both the property manager and owner to stay levelheaded and avoid defensiveness.

These conversations should be scheduled regularly, serving to relieve pressure, keep owners informed, and ensure their properties are up to snuff. Schwab and Goedheid both suggest having inspections and reviews of the home once or twice a year to see what may be improved within the property. This review also gives both owners and managers a chance to speak about potential updates and market conditions.

“We try to get ahead of these things and give them some time to process [changes] but also make sure that they have the ability to set some money aside from their proceeds so that they can keep their home in top shape,” Goedheid says.

One axiom that Schwab suggests property managers keep in mind: This too will pass. That applies to good times and bad times. When every owner is raking in money, that won’t last, just as it won’t last when owners are seeing revenue dip. Through good times, build up for bad times— through bad times, keep working to ensure the business withstands the storm.

Explain Data in Context

Data is perhaps the most powerful tool property managers have, both for communicating with owners and for withstanding tough times. When used in context, property managers can use data to show owners where improvements can be made, or even where business is doing better than it seems during a tough market.

Goedheid uses the company Key Data to show owners how their property is performing compared to others in the market. Owners are typically going to compare revenue with what they made last year. Without data, they’ll likely complain to property managers if they’ve made less money year over year.

“To tackle that, we use a lot of market data,” Goedheid says. “We want to outperform the markets by at least 15% to 20% and show that with objective third-party data.”

If the market is down 30% from the previous year, for example, Goedheid says that his goal is to show owners that their revenue for their property is only down 10% or 15%, still outperforming the market. Putting data into context like this has been essential for his company’s growth, he says, to the point where he’s unsure how he’d have such conversations without data.

Data can also be powerful to show owners where to spend money to improve their business. A property manager can show owners similar properties in the area and what kind of revenue they earn after specific modifications, Goedheid says. He’s also used data to find that a property’s booking calendar can get too full—when a property is booked solid for months in advance, it will make about 20% less per night and will also drop in search results, a fact that often surprises owners.

“Sometimes owners have the completely wrong idea about what’s going on,” Goedheid says. “If you can show them objective third-party data, it’s so helpful. Instead of sharing opinions, show them data-backed insights.”

Most of the data Goedheid gets for Casiola comes from Key Data or AirDNA, two of its software partners, but there are now more data and software options than ever in the vacation rental industry.

Sometimes, Holcomb says, owners want to get into the nitty-gritty, while others do not. Knowing this about each owner goes back to setting expectations, as does letting owners know what pieces of data and which success metrics property managers believe are essential. Does a property manager most value review scores? Nightly rates? How much do reviews matter? A company should know and be able to explain these pieces of data to curious owners.

Acquire in Tough Markets

Although it may seem counterintuitive, a well-managed company can acquire high-quality owners during tough markets.

“It’s actually the best time to recruit new owners, or at least owners coming from other management companies,” Goedheid says. “When their calendar is fully booked, no one is going to want to take the risk of switching property management companies. But the low season? That’s when we see the most movement.”

These are times when owners panic, Goedheid says, and may start to see revenue slip away. If their property managers aren’t nurturing the relationship properly, this may be a time when owners start looking for new management. It’s a good opportunity to recruit property managers who have been succeeding despite the market, especially those who can show success via data.

This is why Holcomb says that it’s essential for all owners to plan for tough times when times are good. On one side, they may be able to recruit new owners; on the other side, they prevent losing unhappy owners through good strategy and communication. “You have to be prepared for the ebbs and flows,” Holcomb says.

Succeeding Through Downturns

When the market has a downturn, revenue is worse than expected, or bookings slow to a crawl, there are steps that both owners and managers can take.

The first step, as Schwab learned when he started his career, is proactive ownership and honesty about the reality of the situation. “Make sure that you reframe it in a way that gives them hope and that you can act upon the situation,” he says. “Highlight the wins but be honest about the fails.”

Being truthful with homeowners can be simple, Schwab says: “I want to tell you about a mess. We said that we were going to do $50,000 in revenue this year, but we’re at $30,000. I want to call you and tell you what’s happening and what the plan is.” Then, property managers can have a discussion with owners about the market conditions, what’s under the control of both, what the data shows, and how they can move forward together.

Transparency keeps the relationship with owners alive, Holcomb says, and this business is all about relationships. The market dropping to where it was before the vacation rental boom of the early 2020s isn’t necessarily a bad thing, but property managers who aren’t clear about what’s happening may lose the trust and business of owners.

“The fastest way to erode a relationship is that you know, not have transparency, not have honesty, not have the authenticity with that owner,” Holcomb says. “The second you start to erode that trust, that owner is walking out the door.”

Once property managers can honestly tell owners what the issues are, both sides can work to improve the situation. A step property managers can take, Goedheid says, is channel diversification and optimization. Property managers can tweak channel performance by looking at ranking optimization, ensuring that each listing is as close to the first page as possible.

“We’re not looking at having the most channels, but we really want to optimize the channels that do work,” he says. “We see that 80% of the bookings are coming from 20% of the channels, and we want to make sure that we maximize the performance on those channels that generate revenue.”

On the owners’ side, many of the improvements will come from working on the property. But Goedheid says that owners and property managers can work together to update the listings—new photos, new headlines, listing local events, ensuring prices are set well. The goal is to ensure that each home is booked at least once a month, he says, even during hard times and low seasons. “We put a lot of effort in making sure that all the different dials are tuned in perfectly,” he says.

One issue that Schwab knows property managers run into is the workload. Often, many don’t have time to think about how they communicate, nor a plan in place—they’re running from issue to issue at properties. But he also knows how well it works to have a plan and says that third-party consultants can help property managers build a communication plan for owners. With a solid plan, even the busiest owners can thrive in tough times.

The overarching theme of communicating through hard times is simple, Schwab says: Focus on what can be controlled. Just like property managers should be honest with homeowners, they must be honest with themselves about their own levels of control. And how a property manager communicates with an owner is in their control, even if the owner’s responses are not.

“This is your portfolio to use or lose,” Schwab says. “If you don’t call your homeowners, that’s how you let them become somebody else’s homeowners.”

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