Short-Term Rental and Outdoor Summit

Original Date May 19, 2021

With our Partners

Watch the Event Recordings

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Our Summit

As vaccines were rolled out and domestic travel looked set for a strong return in 2021, Skift revisited the dramatic shift at the Short-Term Rental and Outdoor sectors during a one-day summit. Last year, Skift hosted this Summit the same week as Airbnb had its IPO, and the short-term rental ecosystem has since seen an influx of investors, acquisitions, and expansion even through the pandemic. Outdoor recreation and travel have also seen an explosion of interest and professionalization as travelers flood regional parks, attractions, and activities in lieu of international destinations.  

We once again brought together leaders from online rental marketplaces, investors, startup founders, and outdoor recreation operators for interviews with Skift editors and research analysts. We uncovered what might happen next in both sectors as their growth outpaced the rest of travel and the big questions facing these sectors, including:

  • How can leisure rentals not only capture summer demand, but also build deeper relationships with this growing market?
  • With so much investment entering the short-term rental market, how will this accelerate consolidation and who will be acquired? 
  • How will outdoor travel continue to attract new travelers and growth?
  • Will rentals attract more business travelers in the future as remote work becomes the norm? 
  • Will transparency and rate parity finally take hold in the rental industry, and how will consumers react? 
  • Can the outdoor recreation industry professionalize without losing the qualities that attracts their core consumer base?

Event Tech Host


Wednesday, May 19th

11:03 AM

Skift Research’s Outlook for Short-Term Rentals in 2021 and Beyond

11:10 AM

Can Vrbo Keep the Momentum Going?

Jeff Hurst

Expedia Group
President and Co-lead, Marketing


Dennis Schaal – Executive Editor, Founding Editor
11:30 AM

What’s Next for Urban and How Will It Bounce Back?

Francis Davidson

Co-Founder & CEO


Sean O’Neill – Senior Travel Tech Editor
11:45 AM

The New Playbook for Short-Term Rental Managers

Julie Brinkman



Jeremy Kressmann – Research Editor
12:00 PM

Technology’s Role in Reshaping Guest Experience, Operations, and the Bottom Line

12:20 PM

Acquisitions and Investments in Short-Term Rentals: Predictions for 2021

Carl Shepherd

Investor and Co-Founder


Dennis Schaal – Executive Editor, Founding Editor
12:45 PM


12:55 PM

What’s Happening on the Ground for Rentals Ahead of Summer

1:20 PM

The Evolution of FLEX Multifamily Buildings: How to Drive Profit and Value for Owners

Will Lucas

Mint House
Founder and CEO


Angela Tupper – Contributor, EventMB
1:35 PM

How Outdoor Travel Startups Are Meeting Consumer Demand

2:00 PM

Outdoor Travel Is Hot: What Are the Opportunities and Challenges?

2:20 PM

Limiting Overtourism Within Public Lands: What It Means for Travel Companies

Rick DeLappe
Interagency Program Manager


Margaret Bailey – SVP, CHM Government Services
2:35 PM

Where Do Short-Term Rentals Go From Here?

3:00 PM

Event Ends

(Subject to change)

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