In this episode, Tom Stewart, COO of Resort Realty, joins Alex & Annie totalk about the realities of running a vacation rental business in the Outer Banks, one of the most established and distinctive markets in the industry. They get into what makes the market different, from its geography and seasonality to its mix of inventory and long-standing operating norms.
Tom also shares what it takes to keep a legacy operation strong as market conditions change. The conversation explores weather and erosion challenges, guest and owner communication, selective growth, direct bookings, linen and laundry logistics, dynamic pricing, onboarding complexity, and the reset in owner expectations after the COVID boom.
If you work in vacation rentals, especially in a mature or highly seasonal market, this episode offers a practical look at what long-term success requires behind the scenes.
Episode Chapters:
00:00 - Welcome to the show
04:20 - Tom Stewart’s path into vacation rentals
08:18 - What makes the Outer Banks such a unique vacation rental market
11:37 - Weather, erosion, road access, and operating through disruption
20:56 - Why legacy markets function differently from newer STR markets
25:05 - Professionally managed inventory and Resort Realty’s direct booking mix
27:18 - Growth vs. scale and why selective inventory matters
30:41 - Laundry, linens, and simplifying operations at scale
36:13 - How Resort Realty approaches dynamic pricing
44:16 - Expanding into long-term rentals and building steadier cash flow
49:01 - Why onboarding large homes is more complex than it looks
54:15 - How owner expectations changed after the COVID boom
58:43 - Why pricing and demand look different now
1:00:38 - Tom’s advice for people getting into vacation rental operations
Connect with Tom:
LinkedIn: https://www.linkedin.com/in/tom-s-8b607938/
Website: https://www.resortrealty.com/
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#vacationrentals #shorttermrentals #outerbanks