Short-Term Rental AND Outdoor Summit

May 19, 2021

Register Below


Our Summit

As vaccines are rolled out and domestic travel looks set for a strong return in 2021, Skift will revisit 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.  

Join us on May 19, on the cusp of a busy summer vacation season, as we once again bring together leaders from online rental marketplaces, investors, startup founders, and outdoor recreation operators for interviews with Skift editors and research analysts. We’ll uncover what might happen next in both sectors as their growth outpaces 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?

When: May 19, 2021
Live at 11 a.m. ET and On-Demand

Where: Skift’s Online Event Platform


(More to be announced)


(Subject to change)

Wednesday, May 19th

11:00 AM


11:03 AM

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

11:10 AM

Are Short-Term Rentals Entering a New Era Post-Pandemic?

Jeff Hurst

Expedia Group
President and Co-lead, Marketing


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

What’s Next for Urban and Tech-Enabled Hospitality?

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 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

A Look at 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

Outdoor Travel Startups: The Opportunities and Challenges Ahead

1:55 PM

What Are Consumers Seeking as Outdoor Travel Booms and Professionalizes?

2:15 PM

Digitizing Public Lands: How Limiting Demand Has Affected Outdoor Travelers

Rick DeLappe

National Park Service
Interagency Program Manager


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

STR Market Predictions: Where Will Tech Disrupt?

3:00 PM

Event Ends


Why You Should Participate

Skift Live events are transformative to businesses and brands.


Learn from the experiences and strategies of the most creative leaders at major travel brands.


Our agendas are jam-packed with opportunities to learn from experts, gain tactical knowledge, and understand the latest trends in travel.


Attendees will hear insights on how tech is disrupting the industry and adapting to consumer demand.

Register Now

Solo Ticket

Full access to the one-day event for one person.


Group booking

Invite up to 7 co-workers with just one purchase.

From $160

Master Pass

Access every event in 2021 live and on-demand.

Join Us

Events take place on Eastern Standard Time (UTC -5).

Can’t attend live? Recordings and presentations will be available on-demand after the Summit.

Tickets to Skift events are non-refundable. After purchasing a ticket, attendees can transfer registration to another person.

Other Ways to Attend


Skift Research subscribers at every level – personal, professional, and enterprise – get 25% off of the full price of registration. Use promo code RESEARCH21 through the Solo Ticket option, above. If you’re not currently signed in, click “Sign In” on the registration page.


Skift Pro subscribers get 15% off the full price of registration. Use promo code PRO21 through the Solo Ticket option, above. If you’re not currently signed in, click “Sign In” on the registration page.


Group Ticket rates begin at two tickets. 

  • Tickets for two attendees are US$80 each  
  • Tickets for three to eight attendees are US$75 each 

You can purchase these through our registration portalSelect the number of tickets you need. Discounts will automatically be applied as you add attendees. 

To purchase more than seven tickets, please contact for details on creating a custom package


Sponsors receive free passes as well as a 25% discount on additional tickets. You find out details about activations, breakout sessions, special events, and other opportunities by emailing our sales team at

Note: For online events we do not offer startup discounts. We have priced these events so that a broader swath of industry professionals can attend.

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