From Loco Gringo to Smart Pineapple: A 20-Year Perspective
An early vacation rental user shares how Kay Walten's vision shaped the past—and is leading the future of AI in hospitality.
I had the privilege of being one of the earliest users of “LocoGringo.com” Kay Walten’s pioneering vacation rental platform in Mexico. Watching it evolve from a grassroots idea into a thriving, trusted marketplace over two decades was nothing short of inspiring. Kay and her team set the standard—her meticulous attention to detail and deep understanding of both guest and host needs made “Loco Gringo” a leader long before the industry caught up.
Fast forward to 2025—our paths crossed again, this time in the world of AI. I stumbled upon the AI for Hospitality community she built on Skool, and it’s been a game changer. In just a few weeks, I’ve gained actionable insights into how AI can improve the guest experience and streamline hosting operations. Kay continues to be ahead of the curve.
Her latest venture, *Smart Pineapple*, is one of the most thoughtfully curated platforms out there for STR hosts—packed with smart tools, practical strategies, and a supportive community. I’m so glad to have reconnected with Kay and am looking forward to the possibility of working together again—this time on a direct booking platform. If you’re in the STR space and want to stay ahead of the curve, follow what Kay is building. She’s the real deal.
- Sai Chandrasekharan, www.dreamvacayescapes.com