The Middle of STR Is Dying And Luxury Is Taking Over
Good Morning Hospitality
04/27/26
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On Monday’s Good Morning Hospitality, A Skift Podcast, Michael Goldin, Brandreth Canaley, Jamie Lane, and Wil Slickers are joined by Sean O'Neill, Senior Hospitality Editor at Skift, to break down a major strategic shift in the short-term rental space.
onefinestay is pulling back from hundreds of urban rentals to focus on ultra-luxury homes and high-end leisure destinations, signaling a broader move toward fewer, higher-quality listings as operators rethink where margins and demand are strongest.
The team also unpacks new data out of New York City showing that 27% of approved short-term rental listings are now operating illegally, highlighting the ongoing tension between regulation and enforcement even after strict laws were put in place. The episode wraps with a look at ChatGPT introducing cost-per-click ads, a shift that brings AI platforms directly into the same performance marketing model that powers Google and OTAs today, raising new questions about who controls travel discovery and demand.
This episode is presented by Vrbo & Bilt. Visit vrbo.com/goodmorning to learn more about how you can earn OneKeyCash for each eligible property you list.
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 Good Morning Hospitality, A Skift Podcast Bonus episode, Brandreth Canaley and Michael Goldin sit down with Tim Rosolio, VP of Vacation Rental Partnerships at Vrbo/Expedia Group, from a standout “Vacation Rental of the Year” property in New Hampshire.
Tim breaks down what actually drives performance on Vrbo today, from must-have amenities and pricing strategies to the growing importance of quality, consistency, and reviews in an increasingly saturated market. He shares why the short-term rental “gold rush” is officially over, and what operators need to do now to stay competitive.
The conversation also dives into Expedia Group’s broader strategy, including the rapid growth of B2B distribution, the expansion of vacation rentals across Expedia’s ecosystem, and how new tools like promotions and sponsored listings are changing visibility and bookings.
They also tackle AI in travel, where it’s already delivering value, where it’s overhyped, and why the human element still matters in hospitality.
Episode Chapters: 00:00 Snowy New Hampshire Setup 01:08 Why This Rental Won 01:26 How Vrbo Picks Homes 02:35 Hosts Who Go All In 05:22 Amenity Must-Haves 07:57 Boosting Rankings Fast 08:25 Promotions That Convert 10:25 Is The Gold Rush Over 12:44 Quality Over Quantity Era 16:58 Standards And Trust Issues 19:00 Cleaning and Reviewing Data 20:26 Reviews Signal Quality 21:36 Star Ratings Confusion 22:26 B2B Growth Expansion 25:09 AI In Travel Tech 26:32 Keeping Human Hospitality 28:16 OneKey On Vrbo 29:48 Sponsored Listings Launch 33:14 Rapid Fire Wrap Up
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Next Episode
On this week’s Good Morning Hospitality, A Skift Podcast: Hotels Edition, Sarah Dandashy and Steve Turk break down Hilton’s latest push into AI with its upcoming ChatGPT app and evolving “Select” deals strategy, and how the company is positioning itself more like a platform that controls pricing, distribution, and guest engagement.
They also explore Hilton’s continued expansion of lifestyle and luxury brands across Asia-Pacific, the shift in ultra-luxury hotels toward curated guest communities, and how budget airlines are now in talks over a $2.5 billion bailout as financial pressure builds across the travel sector.
This episode is presented by Vrbo & Bilt. Visit vrbo.com/goodmorning to learn more about how you can earn OneKeyCash for each eligible property you list.
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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