The Role of AI in Enhancing Short-Term Rental Management

This chapter examines the transformative effects of artificial intelligence on the vacation and short-term rental markets. It highlights the synergy between AI technologies and local expertise, showcasing how operations can be streamlined while preserving the human touch in guest interactions.

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Former Vacasa founder and now Fairly CEO, Eric Breon, joins Jamie Lane to unpack what’s actually driving bookings today—and why reviews now beat everything but rock-bottom pricing. Eric explains how the playing field shifted: pro photos, yield tools, and channel distribution are table stakes; sustained growth comes from a flywheel of 5-star guest experiences that boost ranking, conversion, and RevPAR. He also makes a provocative case that vacation-rental operations suffer diseconomies of scale—and outlines a model that blends centralized automation with hyper-local caretakers who know each home inside and out.

You’ll hear how Fairly separates “guest care” from “back office” to keep teams small, responsive, and review-obsessed while still benefiting from sophisticated distribution, accounting, and pricing. Eric shares candid lessons from scaling Vacasa, why they’re building tech in-house (despite the cost), and where AI helps today (automation, comms assist) versus where human judgment still wins (on-the-ground knowledge and onboarding).

Here are the practical takeaways you can use now:

• Treat reviews as your core growth channel: a 4.9+ average materially lifts RevPAR and ranking, creating a compounding advantage.

• Centralize what software does best (pricing rules, taxes, distribution, smart locks, messaging templates) and localize what guests feel (cleanliness, quick fixes, clear answers).

• Price strategy should reflect owner goals: “hold high” for personal-use homes vs. “fill Tuesdays” for pure investments—your system should support both.

• Start strong on launch: design, amenities, and first-wave reviews set your long-term trajectory.

• Direct vs. OTA is a balance: repeat guests lock in future seasons, but channel conversion still matters for momentum.

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Connect with Eric on social media

LinkedIn: https://www.linkedin.com/in/ericbreon/
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Connect with Jamie on social media

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

Twitter: https://twitter.com/Jamie_Lane

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Connect with Scott on social media