June 10, 2026
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The short-term rental industry has a way of pulling people in and refusing to let go. Richard Vaughton discovered this in 1999 when he left his role running a Finnish public company subsidiary to invest in rental properties. What started as a side venture became a 25-year journey through multiple management companies, a tech startup, hundreds of properties across, and eventually, a consulting practice advising operators worldwide.
His path offers a rare long-view perspective on an industry that most people measure in pre- and post-COVID terms. Richard's timeline stretches back to 2008's financial crisis, through the rise of Airbnb and HomeAway, past the scale-at-all-costs venture capital era, and into today's AI-driven consolidation phase.
"I think this industry involves entrepreneurs, people who actually want to control their own destiny and not be told what to do," Richard explains, whose fundamental mismatch between his personality and corporate employment led him to be his own boss.
After running a franchised service business across nine countries and 40 destinations, he found managing employees taxing. "My expectations were probably too high for most people," he admits.
This entrepreneurial DNA runs through the industry. Former firefighters, lawyers, doctors, dentists, and airline pilots have all left professional careers to manage short-term rentals.
Richard points out that “there seems to be a threshold at 100, which stops most managers growing” and he suspects it’s “down to a lack of investment in staff.”
“I work with managers with 50, 60, 70, 90, 95 properties,” he says, noting that it’s difficult to get over that.
When you're managing 100 properties with six office staff and contracted cleaners, adding another 30-40 properties feels like pure profit opportunity. You're already set up. You have systems. Why not cram in more business and boost your bottom line?
But staff arrangements become more complex the bigger you get, and employing people costs significantly more than it did five years ago.
Many managers try to solve the staffing problem with virtual assistants. The VA industry has seen stratospheric growth in short-term rentals over the past few years. It seems like the perfect solution: lower costs, 24/7 coverage, scalable support.
But virtual assistants don't get you new owners. They can't do the true on-the-ground hospitality. They can't have a beer with an owner on Saturday when they've come down to visit their property and expect personal attention.
"You do have to still invest in people," Richard emphasizes. "And now the virtual assistants are being replaced by AI."
Richard's Italian operation scaled to hundreds of properties quickly. Lake Como in 2006 was virgin territory: Americans wanted to visit where George Clooney bought his villa, new apartments and villas were being built constantly, and local real estate agents weren't capitalizing on short-term rental demand.
"If you can find a virgin territory somewhere on the planet, preferably near water, take it immediately," Richard advises.
The problem? Those territories don't exist anymore. Airbnb and HomeAway's apps exposed the general public to the fact that you can make money from rental properties while building equity. The 2008 property crash accelerated adoption as thousands of people across Europe who'd been flipping properties suddenly needed rental income to cover their loans.
Richard had his AI revelation at a VRMA conference two and a half years ago. He was pulled onto a booth to look at Boom, a PMS built on an AI model from the ground up. The platform could extract business intelligence and automate tasks that previously required office staff pulling their hair out on a minute-by-minute basis.
"It was a bit of a light bulb moment for me," he recalls.
But here's what he's learned from sitting around tables at conferences and small meetings with managers worldwide: 95% of them still aren't really doing much with AI. There's enormous noise but very little activity.
The ones who are using it fall into two camps:
The real transformation is just beginning.
Richard's advice to managers has changed radically in the past few years. Pre-COVID, he recommended finding the best PMS and bolting in best-in-class tools for each category: dynamic pricing, revenue management, guest apps, channel management, and 15+ other categories.
"My advice now is you're going to need a single system for about 12 to 15 of those categories," he explains. "And they are all going to be well embedded within a PMS."
The major platforms “are all building comprehensive, almost operating systems that you can run your business on.” When all your information lives in a single place, AI can access the complete data set to provide business intelligence and automate actions.
Imagine this scenario: A guest books directly through your system. The AI knows your pricing rules, owner restrictions, current occupancy, and whether to offer a discount. It communicates automatically, offers extras, integrates with your guest app, coordinates with the cleaning team, reviews your cleaners' work, and tracks costs, all within a single system.
Certain things remain outside the scope of what AI can currently do:
That last point is temporary though. Dynamic pricing tools are already using AI to give revenue managers better decision-making support. Soon, the AI will simply tell you: "Drop prices 2% over the next two weeks, then add $100 for the weekend because there's an event happening."
The UK is a mature market and “a really good example of what can happen.” Over the past 10-15 years, 300-500 properties have been rolled up into super managers:
Richard's own UK company was acquired as part of one of these roll-ups.
Europe hasn't experienced this yet. Thousands of small managers operate with an average of 30-65 properties, but they struggle to grow as the environment becomes more challenging. OTAs are taking more money, and costs are increasing.
"You can expect roll-ups in Europe in the prime destinations," Richard predicts.
"We are turning into an enterprise business. It's got legislation, it's got governance, it's got dangers everywhere. And only the large can actually defend against these things at scale."
Registration requirements are spreading globally. Licensing and planning restrictions are increasing. Health and safety compliance is mandatory. Fire regulations are tightening. Insurance requirements are rising.
Individual hosts who run excellent operations will survive: “if you run a good short-term rental as an individual, you will care about health and safety. You will care about all those elements of your business that have to be addressed. So the cream rises to the top there, and you will get very, very good, well-reviewed, independent short-term renters.”
Over the past two years, Richard has spoken with dozens of urban managers at conferences. They all describe the same challenge: running 60-80 properties distributed across London (or any major city) is operationally brutal.
"They're all saying, I need a block of apartments. I need a single block to actually manage," Richard notes.
The future of urban short-term rentals is industrial-scale operations running purpose-built apartment hotels. Guest demand remains strong as people still want short-term rentals in cities, but what's fulfilling that demand is changing.
These new apartment hotels maintain a higher general standard than distributed portfolios. They never exceed expectations, but they never disappoint either. They deliver exactly what guests expect, with operational efficiency that distributed portfolios can't match.
Richard has sold multiple businesses in his career, and he now advises on M&A deals regularly. The pattern is consistent: most businesses don't sell because they planned it, but because they have to.
Personal reasons. Financial weakness. Market pressure. A realization that competitors are about to crush them.
If you're over 55 and running a management company with a decent portfolio, you're a target for acquisition. But being acquirable requires preparation.
Start planning two or three years before you want to sell. Richard advises to “set your goals out as to how you’re going to put your business in decent shape so that you are acquirable and of interest.”
The pre-COVID era was about scale, but today's buyers ask:
“The other thing I say to everybody I work with is get yourself out there and start networking.”
Richard gets asked this question constantly. His answer is specific:
"I would focus on great quality accommodation that sleeps eight people in great locations. And I would use an enterprise level technology stack immediately. I would bolt in as much hardware as I possibly could, but I would actually have some people involved as well."
The human element still matters. “We’ve had hundreds of thousands of years of connectivity talking to each other, looking at each other, facial expressions.” These remain powerful tools that technology can't fully replace.
He'd cap the portfolio at 50 properties, not chase scale. “You can probably make as much money out of 50 really good ones as you can out of 5,000 urban ones.”
Twenty-five years in an industry teaches you to recognize patterns. The current AI transformation is the most significant operational shift since online booking platforms emerged. Likewise the consolidation pressure isn't temporary, it's the natural evolution of a maturing industry facing regulatory complexity.
But the fundamentals haven't changed. Guests still want great places to stay. Owners still want their properties managed well. The operators who succeed will be those who use technology to handle the repeatable tasks while preserving the human judgment that separates good hospitality from automated mediocrity.
The industry is professionalizing. The barriers to entry are rising. The margin for error is shrinking. And the opportunity for operators who adapt remains enormous.
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