Shahar Goldboim
May 20, 2025
What AI-powered search means for vacation rental brands — and how to prepare for the shift.
Planning a vacation used to feel like putting together a 5,000 piece jigsaw puzzle — with your mother-in-law.
Pick your dates. Choose a destination. Open 12 tabs. Skim 30 reviews. See if you can find a better price elsewhere. Share with the family. Wait for feedback and do it all over again when they hate all your options.
But with AI, the days of needing a vacation from vacation planning are behind us.
You can now ask your AI agent of choice to do the planning for you.
“We’re a family of four (plus a dog), and we want to go to the beach for a week in July, within a short flight from home. Ocean view, a barbecue, and fun activities for the kids. All in under $5,000 — flights, stay, and rental car included. What do you recommend?”
No tabs. No filters. No friction.
Just intent — and an AI that delivers the answer. Welcome to the new era of travel planning.
From keywords to comprehension
For years, SEO ruled the digital marketing playbook, and vacation rental booking sites were no exception. You stuffed your site with “vacation rental” + [location], crafted keyword-rich blog posts, and paid for Google ads to compete with the likes of Airbnb and Booking.com.
But Large Language Models (LLMs) like ChatGPT, Gemini, and Claude are replacing the traditional search engine experience. What travelers want isn’t “10 best dog-friendly villas in Myrtle Beach”. They want one good answer — tailored to them, their taste, and their budget.
That means the future of search isn’t about ranking. It’s about relevance.
What about OTAs?
Online Travel Agencies (OTAs) like Airbnb and Expedia are powerful because they aggregate supply, simplify comparisons, and give users a sense of trust. But AI could take their competitive edge away and level the playing field with direct booking sites.
AI doesn’t need filters. It doesn’t need your brand to be on page one of Google. It just needs access to structured, quality data about your inventory.
In other words, the AI doesn't care if you’re an OTA or a single brand. It just wants the best fit, at the best price.
Direct booking sites that adapt now will build AI’s trust and be a step ahead as more and more guests use LLMs to find their perfect vacation.
While some of this may be helpful for SEO too, it’s a different kind of optimization, and those who prepare now for AI search to go mainstream will be the winners of tomorrow’s bookings.
How property managers can get ready
The travel discovery funnel is about to collapse into a single chat. So how do you make sure you’re part of it?
Here are five ways to prepare:
- Structure your data
- Ensure your property listings have clean, rich metadata: detailed descriptions, amenities, high-quality images, and guest personas. AI thrives on structured inputs.
- Ensure your property listings have clean, rich metadata: detailed descriptions, amenities, high-quality images, and guest personas. AI thrives on structured inputs.
- Expand your digital footprint
- Publish content that reflects the guest experience more broadly: think travel tips, itineraries, stories. The more semantically rich your content is, the more LLMs can understand and surface it. In many ways, AI thinks more like a human in this way.
- Publish content that reflects the guest experience more broadly: think travel tips, itineraries, stories. The more semantically rich your content is, the more LLMs can understand and surface it. In many ways, AI thinks more like a human in this way.
- Connect your systems
- AI models increasingly pull from connected APIs and knowledge graphs. Make sure your booking engine, pricing tools, and guest data platforms are accessible and aligned.
- AI models increasingly pull from connected APIs and knowledge graphs. Make sure your booking engine, pricing tools, and guest data platforms are accessible and aligned.
- Build trust across platforms
- AI thinks about trust much more like a human than Google search rankings ever did. That means that it won’t automatically trust your website — instead, it will look for external validation. That means you need to be in local press, blogs, and review sites to build AI’s trust in your product.
There’s a revolution coming in how guests find and book their travel. If SEO was about visibility, this new wave is about trust.
Vacation rental pros who understand that — and act on it now — will lead the way as we move into this new way of searching.
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