The vacation rental industry has been through a lot of growth, change, and recalibration over the last few years.
Companies have scaled quickly, larger players consolidated, AI entered the scene, distribution became more complex, and for many operators, the business itself became harder to navigate.
But for Bob Milne, President and COO of First Chair Destinations, the future of the industry still comes back to something very familiar: local hospitality.
In this episode, Bob joins Alex & Annie to share what he has learned from building and scaling vacation rental companies across Steamboat Resorts, Wyndham Vacation Rentals, Vacasa, Casago, and now First Chair Destinations.
We discuss:
→ What rapid growth has taught the vacation rental industry
→ How hospitality can get lost as companies grow
→ What operators can learn from the Vacasa to Casago transition
→ Where AI can support vacation rental operations
→ Why OTAs still play a major role in distribution
→ How owner expectations around channel visibility are changing
→ Why the future of vacation rentals is still local
#vacationrentals #shorttermrentals #strindustry #propertymanagement #hospitality