Send us a message!In this episode, Tom Stewart, COO of Resort Realty, joins Alex & Annie to talk 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:04:20 - Tom Stewart’s path into vacation rentals08:18 - What makes the Outer Banks such a unique vacation rental market11:37 - Weather, erosion, road access, and operating through disruption20:56 - Why legacy markets function differently from newer STR markets25:05 - Professionally managed inventory and Resort Realty’s direct booking mix27:18 - Growth vs. scale and why selective inventory matters30:41 - Laundry, linens, and simplifying operations at scale36:13 - How Resort Realty approaches dynamic pricing44:16 - Expanding into long-term rentals and building steadier cash flow49:01 - Why onboarding large homes is more complex than it looks54:15 - How owner expectations changed after the COVID boom58:43 - Why pricing and demand look different now1:00:38 - Tom’s advice for people getting into vacation rental operationsConnect with Tom:LinkedIn: https://www.linkedin.com/in/tom-s-8b607938/ Website: https://www.resortrealty.com/ ✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/ Reach more guests across top travel sites with BookingPal.Alex & Annie listeners get onboarding fees waived + 20% off the first two months.👉 Click here to get started: https://alex-and-annie-offer.bookingpal.com/#vacationrentals #shorttermrentals #outerbanks

Ask this episode

“What did the council decide on item 42?” — answered with the speaker and the moment.

Transcript

Related