What “AI-Bookable” Actually Means for Hotels & STRs
Good Morning Hospitality
05/25/26
•33m
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On this special holiday episode of Good Morning Hospitality, Brandy Canaley and Michael Goldin unpack one of the biggest shifts happening in travel right now: AI-powered booking. Joined by Jason Cincotta, founder of Kismet, the conversation breaks down Google’s new push into agentic hotel booking, what it means to become “AI-bookable,” and why independent hotels and vacation rentals may need to rethink how they show up online.
The episode also dives into Airbnb’s massive Summer Release, including boutique hotels, AI-powered review tools, airport pickups, grocery delivery, rental cars, and the company’s expanding push toward becoming a full trip platform. Michael and Brandy debate whether Airbnb’s latest features are meaningful product evolution or just great PR, while also exploring how AI could reshape direct bookings, loyalty, and the future of travel planning.
This episode is presented by Plusgrade & Bilt. Visit plusgrade.com to learn more.
And for hotels with restaurants and restaurant owners, Bilt Hospitality is finally here. Go to joinbilt.com/gmh to learn more.
Previous Episode
In this special GMH Bonus episode, Jamie Lane sits down live in San Francisco with Airbnb Chief Business Officer Dave Stephenson following Airbnb’s 2026 Summer Release event.
The conversation breaks down Airbnb’s biggest updates, including expanded hotel distribution, new AI-powered search and personalization tools, rental cars, airport pickups, grocery delivery partnerships, and the continued push into experiences and services.
Jamie and Dave also dive into Airbnb’s growing hotel strategy, why the company believes boutique and independent hotels are a major opportunity, and how Airbnb may have quietly created one of the most powerful loyalty flywheels in travel through hotel booking credits tied to future home stays.
They also discuss how AI is reshaping the Airbnb experience, from personalized listings and review summaries to smarter trip planning and guest discovery, plus what these updates could mean for hosts, operators, and the broader OTA landscape moving forward.
Next Episode
On this week's Good Morning Hospitality, A Skift Podcast: Hotels Edition, Sarah Dandashy and Steve Turk break down a week where three big stories all pointed at the same shift: the distribution, loyalty, and infrastructure layers of hospitality are all getting reshuffled at once.
The conversation opens with Airbnb naming Andrea D'Amico, an 18-year Booking.com veteran, as its new VP of Hotels, and what that hire says about how seriously Airbnb is coming for the boutique and independent hotel market.
From there, Sarah and Steve dig into why boutique brands like Room Mate Hotels are running out of room on loyalty, and what the SpaceX IPO filing reveals about how deeply STARLINK has already embedded itself into travel's connectivity infrastructure.
This episode is presented by Plusgrade & Bilt. Visit plusgrade.com to learn more.
And for hotels with restaurants and restaurant owners, Bilt Hospitality is finally here. Go to joinbilt.com/gmh to learn more.
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