How Short Term Rental Hosts Should Actually Use AI in 2026

Welcome to Boostly, where we help STR and MTR owners, hosts and property managers get more direct bookings, rely less on OTAs, and build stronger hospitality businesses. 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. Join the Skool group here https://www.skool.com/drive-direct-bo... This was a proper conversation about what hosts, property managers and direct booking businesses should be paying attention to right now, especially with so many new AI tools, website builders, PMS updates and content platforms appearing every week. We covered AI, WordPress, PMS platforms, direct booking websites, guest communication, content, search, community, brand building and the future of hospitality tech. A big thank you to Stay Direct for inviting me into their monthly session and for leading such a strong discussion around what is changing in the industry. You can join the Stay Direct Skool group using the link in the description below. In this episode, 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 moving into 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 human storytelling still matters 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 We also mentioned and discussed: Graeme from Forge, and the work they are doing with AI agents The Scale conference, where AI in hospitality was a major topic Neely Khan, and the importance of storytelling, brand and being chosen, not just discovered Richard Vaughton Boris from Onseason Gil Kahn from Crafted Stays Gareth, who joined the discussion around AI search and discovery Guesty, and how PMS platforms are starting to move faster with 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 changing how operators work The main message from this episode 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, improve operations and make better decisions faster. 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, this episode will help you cut through the noise. This video is part of our free training series to help you grow your short-term rental business and take control away from the OTAs. No gatekeeping. No ads. Just the tools, training and support to help you build the hospitality brand you deserve. Disclosure Information shared in this video is for educational purposes only. Individuals and business owners should evaluate their own business strategies and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary. Copyright © 2026 Boostly