We spotlight two powerful strategies reshaping hospitality—one driven by global tech and data, the other by hyper-local design and service consistency.
Booking Holdings Doubles Down on AI
Booking Holdings just delivered a strong Q2 earnings report, showing 8% growth in room nights and a 13% increase in gross bookings, totalling $46.7 billion. Growth was particularly strong in Europe and Asia, while the U.S. continues to show softer demand due to shorter booking windows and cautious consumer spending.
A major driver of this growth? Booking’s expanding AI infrastructure. Key highlights include:
Priceline’s “Penny” voice assistant, making AI more accessible to travellers.
Kayak.AI’s conversational tools, improving the search-to-booking experience.
Strategic partnerships with OpenAI, Microsoft, and Amazon, aimed at building “agentic” travel planning tools that offer intelligent itinerary curation, personalised suggestions, and seamless multi-product booking.
CEO Glenn Fogel notes that Booking.com is seeing more multi-vertical bookings (like flights + hotels), which is a clear signal that their Connected Trip strategy is working. And with a focus on loyalty, personalisation, and reducing friction, Booking’s AI-first vision could reshape how consumers interact with travel altogether.
Evermore Orlando: Vacation Rentals Reimagined
While Booking is leading on tech, Dart Interests is making waves with a completely different model: Evermore Orlando, a $2.5 billion resort that blurs the lines between hotel and vacation rental.
Key differentiators:
No private ownership: Dart owns and operates every unit.
Hybrid inventory: Offers both hotel rooms and large vacation homes under Hilton management, tied into the Hilton Honors loyalty ecosystem.
Anti-theme park design: Despite its proximity to Walt Disney World, Evermore is all about calm, nature-inspired spaces—no roller coasters in sight.
Operational innovation: In-house staffing, full-time employees, and new F&B and landscaping models aimed at quality control and guest satisfaction.
Evermore is built for multigenerational travel, offering the space and flexibility of STRs with the consistency of a premium hotel stay. With plans to expand into lake, mountain, and coastal destinations, Dart’s model could become a compelling alternative to the fragmented vacation rental market.
Final Thought
Whether it’s Booking’s pursuit of AI-powered global travel, or Dart’s meticulously designed hospitality experience at Evermore, one thing is clear: the future of travel isn’t about choosing between tech and service—it’s about integrating both in ways that put the guest first.