Are you a stressed traveler?
Do you worry about connection times and when to schedule indoor and outdoor activities?
If you answered “yes”, then you’re not alone.
Travel can be stressful, but technology is evolving fast and aims to reduce pressure throughout the journey. The goal goes further, because the next wave of tools will also inspire travelers before they start planning a trip.
Our podcast guest this week, sees this as the next chapter for travel. AI will reshape planning and decision making, and it will shift expectations across the STR space.
There is one important detail to remember. You should not rely entirely on AI. The core standard that drives success in the STR industry stays the same:
You must deliver more than expected.
STR Global Unlocked Podcast | Episode 9
EPISODE 9 WITH GLENN FOGEL, PRESIDENT AND CEO OF BOOKING HOLDINGS
Chances are, this has happened to you. You organize your next trip and feel confident about every detail. Then you notice the connection window is too small. Any delay means you will miss your flight. Or you realize you booked a service for the day before you arrive.
These small, and sometimes large, mistakes shift the tone of a trip and add stress to something meant to feel relaxing.
Glenn Fogel wants to remove this uncertainty and plans to use AI to do it. As the CEO and President of Booking Holdings, the parent company of Booking.com, Priceline, Kayak, and others, he sees the rise of AI as an opportunity to build the next level of travel; the connected vision, from start to finish.
This vision goes beyond suitable connection times. It includes booking activities based on weather predictions and receiving inspiration for trips, even before you start planning.
Booking.com has taken early steps toward this future, although there is still a lot to learn and a significant amount of uncertainty surrounding AI.
Glenn sat down with Simon Lehmann, CEO of AJL Atelier, to share how Booking.com views the future of OTAs and the STR industry. He believes the companies that stay in the race are those that move with technology and adapt fast to industry shifts.
In this conversation, we discuss:
How AI is reshaping travel search through natural-language queries, proactive trip planning and Booking’s early work with OpenAI, Google Gemini and other models.
Why short-term rentals are now a core growth engine for Booking.com, representing 36% of room nights and outpacing hotel inventory growth globally.
What the Connected Trip means for travelers and how Booking plans to reduce friction with predictive tools, better timing, automated fixes and personalized recommendations.
The strategic challenges in the US and Asia and how Booking is rebuilding its STR product to win listings, improve quality and meet rising market expectations.
The rising role of FinTech in travel including payments, fraud prevention, cancellations, insurance and cross-border settlement designed to reduce friction for partners and guests.
How regulation, consumer behavior and post-pandemic trends are reshaping STR supply, demand patterns and the long-term future of global travel.
🎧 This week's episode of STR Global Unlocked features Glenn Fogel, CEO & President of Booking Holdings.
Coming up!
Close out 2025 with one of the most important conferences in the industry. Join Simon at the Vacation Rental Data, AI and Revenue Management (DARM) Conference from December 1 to December 3.
Source: Simon Lehmann at his last conference in DARM
Simon wants to connect with brilliant minds to hear more interesting stories, so don’t be afraid to walk up and say hi! Check out his comment to learn more!
Key STR Trends
INDUSTRY CHECK-IN
The goal was simple. Investors would buy small businesses with solid revenue, and strong reputations in their local markets. They would integrate everything into one company, sell it, and profit.
Problems appeared quickly. The one-size-fits-all model left many groups behind, from customers to contractors. The impact ranged from no reimbursement to sudden contract termination.
Higher interest rates have dissuaded homeowners from moving in recent years, which has weighed on the remodeling work that typically happens when houses change hands.
Source: Tag Christof for The New York Times
This took place while consolidation moved forward across many industries, including STR. As mentioned in other issues, STR has a unique trait. No destination is alike, and this creates direct tension with consolidation models built on uniformity.
Industry expert Nir Mairmon explained in a recent LinkedIn post that the priority is choosing the right path to protect core values such as culture and experiences.
Consolidation in STR is still far away, as Simon Lehmann often notes. In the meantime, many small companies face the consequences.
Weekly News
WORTH A READ
Stay on top of the industry. Each issue brings you key insights, major headlines, and the latest tech shaping travel and short-term rentals.
World Cup drives demand
Short-term rental demand is rising ahead of the 2026 World Cup, even though the final locations for many teams remain uncertain.
Pool safety requirements
Pool safety is becoming a major topic for vacation rentals in Florida as one lawmaker pushes for new legislation.
North Carolina Insurance Hike
A proposed insurance increase of close to 70 percent could reshape the STR industry in the state, and others might follow.
CLOSING THOUGHTS
Many people see AI customer support as a simple chatbot, but it offers far more. The question is whether it will shape the future of travel.
The potential exists to build a fully immersive travel experience, one that considers every stage, from planning to handling unexpected changes.
This gives teams space to focus on delivering the best experience.
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