In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Bob Milne, President and COO of First Chair Destinations.

Bob has spent decades in the vacation rental industry, with leadership experience across Steamboat Resorts, Wyndham Vacation Rentals, Vacasa, Casago, and now First Chair Destinations. His career has taken him from building a local vacation rental company in Colorado to helping lead large-scale portfolios across some of the most recognizable names in the industry.

Now, with First Chair Destinations, Bob is returning to a more focused, locally grounded model of vacation rental management.

Throughout the conversation, Bob shares what he has learned from building and scaling vacation rental companies, what the industry can take away from the Vacasa to Casago transition, and why the future of vacation rental management still depends on strong local teams, trusted owner relationships, and consistent guest hospitality.

He also discusses the role of technology, AI, distribution, OTAs, private equity, and consolidation in shaping what comes next for the industry.

Episode Chapters:

03:22 - Bob’s path through Steamboat, Wyndham, Vacasa, Casago, and First Chair

06:26 - What the Vacasa to Casago transition revealed about the industry

10:25 - How First Chair is approaching its next chapter

15:29 - What rapid growth has taught the vacation rental industry

16:18 - Why local teams still matter in a scaled industry

17:05 - How hospitality can get lost as companies grow

23:56 - What operators can learn from the Vacasa to Casago transition

27:51 - What consolidation could mean for the industry

30:06 - Where AI can support vacation rental operations

33:16 - Building a hospitality-first culture across local teams

40:47 - Why OTAs still play a major role in distribution

46:56 - How owner expectations around channel visibility are changing

49:34 - Why the future of vacation rentals is still local

51:57 - How guest expectations are changing

Connect with Bob:

LinkedIn: https://www.linkedin.com/in/robertemilne/

Website: https://www.firstchair.com/

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#vacationrentals #shorttermrentals #local

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