Imagine planning the perfect family trip. After scrolling through what feels like endless listings, you finally make your choice. But when you arrive, it’s just… okay. Not bad, not great and it shouldn’t feel that way.
If you’ve ever had that experience, you’re not alone. The vacation rental industry grew fast, but somewhere along the way, something got lost. The big players are starting to look the same, and the guest ends up paying the price.
Now, one industry expert is calling them out.
STR Global Unlocked Podcast | Episode 4
EPISODE 4 WITH CARL SHEPHERD, HOMEAWAY CO-FOUNDER AND INDUSTRY EXPERT
Carl Shepherd helped shape what the short-term rental industry is today when he co-founded HomeAway. Together with Brian Sharples, he built the company into a global powerhouse that later sold to Expedia for $3.9 billion.
But Carl has a little secret: when he’s on vacation with his family, he usually stays at a hotel. The reason is simple (and it should worry the vacation rental sector). Most rentals feel exactly the same.
It’s become a cookie-cutter model, lacking character or local touch. Even worse, too many property managers aren’t maintaining their properties with care.
That’s just one of several uncomfortable truths Carl shares about the state of vacation rentals. A straight shooter by nature, he doesn’t hold back. As an advisor, board member, and investor in the STR industry, his words carry weight.
“It even makes me sad. When a user has a bad experience, you haven’t just hurt your brand. You’ve poisoned that person for the entire industry.”
He sat down with Simon Lehmann, CEO of AJL Atelier, to talk about where the industry is headed and much more. Their conversation covers:
How an early pivot saved HomeAway by shifting from an information business to a true travel company.
Why the era of astronomical growth may be over, and why replicating success might only be possible in another industry.
How property managers are failing to protect their brands, losing customers for good and raising the question of where those guests will go next.
Why a vacation rental company isn’t a tech company, and why it shouldn’t try to be one. Instead, operators should invest in what truly matters.
🎧 This week’s episode of STR Global Unlocked features Carl Shepherd Co-Founder of HomeAway.
Watch our episode here.
Key STR Trends
INDUSTRY CHECK-IN
The hospitality industry has a major hygiene problem. Whether it’s a single vacation rental, a short-term platform, or a global hotel chain, waste is everywhere and not the kind you might think.
For years, the industry has built isolated systems for every function, from property management to CRMs. Different tools, different languages, all within the same company. The result? Massive data waste.
Many believe AI will fix this. But one expert warns that unless the industry cleans up its data first, the problem could grow even worse once AI takes hold.
Source: Logic Monitor
This article breaks down what everyone, from property managers to hotel operators, needs to do to harness AI effectively and turn data from clutter into competitive advantage.
Weekly News
WORTH A READ
Want to stay on top of the industry? Each issue brings you key insights, current news, and the latest tech shaping travel and short-term rentals.
U.S. OTAs are betting on three big moves
To reignite a slowing market. Here’s how loyalty programs, AI, and B2B services could change the game.
One company is redefining the vacation rental experience
Moving beyond the cookie-cutter model to offer stays that are truly “cool” and “unexpected.”
OTAs are now partnering with ChatGPT
To build travel-planning apps that enhance user interaction and booking experiences.
CLOSING THOUGHTS
There are some uncomfortable truths in the short-term rental and vacation rental industry and someone has to say them.
Today’s guest does just that, sharing insights on what property managers and owners should be doing differently.
Forget the flashy design upgrades or expensive tech stacks. The real opportunity lies in getting back to basics: delivering the best possible experience for the guest.
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