From AI to Evermore: How Booking and Dart Are Redefining Travel
30 Jul 2025 · 4 min
Bob discusses how Booking Holdings uses AI to drive growth and how Dart Interests is building a new kind of resort. The episode covers short-term rentals, travel tech, and what's changing in hospitality right now.
Welcome to episode 294 of the STR Daily podcast powered by Boostly, the industry's first aid driven show for short term rental professionals. I'm Bob your host, bringing you the latest news, trends and insights in travel, AI and hospitality. Whether you're a host, property manager or industry expert, this podcast is your go to source for staying ahead in the fast moving world of short term rentals. Our mission to equip you with actionable strategies and updates so you can navigate the industry with confidence. Hit that subscribe button and never miss an upload in today's episode. First up, Booking holdings continues to show its strength globally, reporting strong Q2 earnings with 8% room night growth and a 13% increase in gross bookings totaling $46.7 billion. Growth was led by Europe and Asia, with the US still lagging behind due to shorter booking windows and more cautious consumer behavior. The company's connected trip strategy is gaining traction with more travelers booking multiple verticals like flights and hotels through booking.com, which now accounts for a low double digit share of transactions and is up over 30% year on year. CEO Glenn Fogle attributes this growth in part to Booking's AI driven initiatives such as expanding Priceline's voice assistant Penny, enhancing Kayak AI's conversational tools and collaborating with OpenAI, Microsoft and Amazon to push forward agentic travel planning. All of this supports their long term vision, a seamless AI enhanced travel experience that boosts both customer loyalty and partner demand. Meanwhile, Dart Interests is taking a very different approach to innovation with Evermore Orlando, a $2.5 billion resort designed from the ground up to blend hotel level service with vacation rental scale. Adjacent to Walt Disney World, Evermore offers a unique hybrid of hotel rooms and large format vacation homes all under Hilton management and loyalty programs. Unlike platforms like Airbnb, none of these homes are privately owned. Instead, Dart owns, operates and services every unit ensuring consistent guest experience. The resort is intentionally anti theme park in its design, favoring calm spaces and natural beauty over high energy attractions. It's also experimenting with new approaches to F and B operations, landscaping and staffing, favoring full time employees over contractors. For Dart, this is a long term play focused on multi generational group travel with expansion plans into coastal, lake and mountain destinations. Together, Booking's global tech led strategy and Dart's ground level reimagining of hospitality show that the future of travel isn't one size fits all, but it is getting smarter, more tailored and more guest centric than ever before. And if you'd like a shout out on the podcast. Leave a review we love hearing from our listeners and your feedback helps us improve. Also, don't forget to share this podcast with your industry peers. Tag Boostly UK on social media when you do, and we'll be sure to share it too. Thanks for tuning in. And remember, Book Direct.
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