In this episode of the Boostly Podcast, I joined the Stay Direct monthly meet-up to talk about where AI is really heading in the short-term rental industry, and what hosts, property managers and direct booking businesses should be paying attention to right now.

Skool Group - https://www.skool.com/drive-direct-bookings-for-strs-5526

This was a thorough deep dive into AI, WordPress, PMS platforms, direct-booking websites, guest communication, content, search, community, and the future of hospitality tech.

Big shoutout to Stay Direct for inviting me into their monthly session and for leading such a strong conversation around what is changing in the industry.

We also mentioned and discussed:

Graeme from Forge, and the work they are doing with AI agents

Neely Khan, and the importance of storytelling and being chosen, not just discovered

Richard Vaughton

Boris from Onseason

Gil from Crafted Stays

Gareth, who joined the discussion around AI search and discovery

Gareth's Linkedin https://www.linkedin.com/in/ACoAABnNNhwBMQ1NDdjPM8JO3TjGvDSe0NZB50c?skipRedirect=true

Guesty, and how PMS platforms are moving into AI

Hospitable, including an example of a host using AI to find booking opportunities

Claude, ChatGPT, Perplexity, OpenClaw, Lovable, Replit, HubSpot and other AI tools are changing how operators work

The main message from the session is simple:

AI is not here to replace your story, your brand, or your relationships.

But it can help you remove boring work, spot missed revenue, follow up with guests, review costs, research leads, and make better decisions faster.

We talked about:

Whether WordPress is still the best option for direct booking websites

Why AI website builders are exciting but not always ready for proper booking flows

How PMS companies are adapting to AI

How hosts can connect PMS data to AI tools

How one host generated $7,000 in bookings within 72 hours using AI

Why AI generated content is often weak

Why community and brand are becoming more important

How ChatGPT, Claude, Gemini and Perplexity are changing online discovery

Why niche brands will be easier for AI tools to recommend

What short-term rental hosts should focus on over the next 12 months

This session was part of the Stay Direct monthly meet-up.

You can join the Stay Direct school group using the link in the description below.

Watch this if you are a host, property manager, website builder, PMS user, or short-term rental business owner trying to understand how AI fits into your direct booking strategy.

Alistair's Linkedin https://www.linkedin.com/in/alistairmalins/