The way travelers discover vacation rentals is changing.
Traditional Google search still matters, but discovery is increasingly expanding into tools like ChatGPT, Gemini, and Claude, where travelers can describe the kind of trip they want and receive recommendations based on that intent.
In this episode, Alex & Annie sit down with Gil Chan, Founder and CEO of CraftedStays, to explore what this shift means for vacation rental operators and the direct booking websites they have spent years building.
Gil shares how his experience as a property manager, combined with his background in e-commerce and product development, led him to build CraftedStays around a problem he saw firsthand: vacation rental websites often lack the infrastructure needed to support a seamless, measurable direct booking journey.
The conversation also dives into how AI search is changing website strategy, what CraftedStays has learned from its research into AI visibility, and why content, structured data, reviews, and strong local expertise may become even more important as the search journey evolves.
Episode Chapters:
00:00 - Welcome to the show
05:39 - Why direct bookings are still complicated
06:56 - What vacation rental websites can learn from e-commerce
16:52 - Building a website platform that can evolve faster
18:55 - CraftedStays’ relationship with Google and the development of Aria
22:56 - From Google search to conversational travel discovery
28:34 - Reviews, structured data, and helping AI understand your business
32:07 - What CraftedStays learned from 24,000 AI search queries
36:53 - Using AI to create and optimize direct booking landing pages
48:13 - Where independent operators can compete with OTAs in AI search
50:12 - How to audit your visibility across AI search platforms
55:35 - Why there is no “page two” in AI search
Want to dig deeper into AI search?
CraftedStays has created a free AI Search Guide for vacation rental operators that breaks down what property managers should be paying attention to as search continues to evolve.
👉 Explore the guide: https://craftedstays.co/ai-search-for-vacation-rentals/
Connect with Gil:
LinkedIn: https://www.linkedin.com/in/thegilbertchan/
Learn more about CraftedStays:
Website: https://craftedstays.co/alexannie/
✨ Exclusive Offer to Alex & Annie Listeners:
Build a direct booking site designed to get found and convert with CraftedStays.
Turn more visitors into direct bookings with less manual work.
👉 Get started: https://craftedstays.co/alexannie/
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/
Reach more direct-booking travelers with Savvy.
List your professionally managed properties for free.
👉 Get started here: https://savvy.com/list
#vacationrentals #shorttermrentals #directbookingwebsite