From National Scale to Local Strength: Bob Milne on Vacasa, Casago, and First Chair Destinations

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Previously titled “Why the Future of the Vacation Rental Industry Is Still Local with Bob Milne of First Chair Destinations” — renamed by the publisher on Aug 3, 2026

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Recorded24 Jun 2026

Publisherfeeds.buzzsprout.com

Handlerec:19043485

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Send us a message!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 Chair06:26 - What the Vacasa to Casago transition revealed about the industry10:25 - How First Chair is approaching its next chapter15:29 - What rapid growth has taught the vacation rental industry16:18 - Why local teams still matter in a scaled industry17:05 - How hospitality can get lost as companies grow23:56 - What operators can learn from the Vacasa to Casago transition27:51 - What consolidation could mean for the industry30:06 - Where AI can support vacation rental operations33:16 - Building a hospitality-first culture across local teams40:47 - Why OTAs still play a major role in distribution46:56 - How owner expectations around channel visibility are changing49:34 - Why the future of vacation rentals is still local51:57 - How guest expectations are changingConnect with Bob:LinkedIn: https://www.linkedin.com/in/robertemilne/ Website: https://www.firstchair.com/ ✨ Exclusive Offers to Alex & Annie Listeners: Thinking about the next chapter for your vacation rental business? Connect with Monarch Collective to explore what growth could look like with the right platform behind you.👉 Learn more: https://gomonarch.com/partnerships/ Automate your short-term rental operations with Hospitable.Start a 14-day free trial and get 25% off your bill for the first 6 months.👉 Get started: https://hospitable.com/partners/alex-annie Reach more guests across top travel sites with BookingPal.Alex & Annie listeners get onboarding fees waived + 20% off the first two months.👉 Get started: https://alex-and-annie-offer.bookingpal.com/ #vacationrentals #shorttermrentals #local

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