Vacation Rental Predictions 2026: AI, OTAs, Regulations and More | Hostaway LIVE!

The vacation rental industry is heading into 2026 with widening performance gaps, fast‑rising AI, shifting guest behavior, and mounting regulatory pressure. In this deep‑dive webinar, Hostaway brings together top data, OTA, and property management leaders to unpack what actually happened in 2025 —and what you must change to win in 2026. Whether you manage 10 properties or 1,000, this session will help you understand who will thrive, who will struggle (and why) — and give you specific moves to make sure you’re on the winning side in 2026. Here's who you'll hear from 👇 Marcus Rader Co-Founder & CEO at Hostaway Andrew Kitchell CEO & Founder at Wheelhouse Simon Lehmann CEO & Founder at AJL Atelier Jason Sprenkle CEO at Key Data Roemer Visser Global Head of Managed Connectivity Partners at Booking.com Steve Schwab CEO at Casago/Vacasa Koryn Okey VP Community & Engagement at Breezeway Jessica Gillingham Founder & CEO at Abode Worldwide (Panel Moderator) Chapters 00:00 – Intro & agenda 00:25 – 2025 in review: widening gaps & climate shocks 04:23 – Big surprises of 2025: supply, margins & Airbnb’s model 05:57 – Data outlook: demand, ADR & booking patterns for 2026 11:37 – Hostaway view: K‑shaped recovery & shifting travel flows 17:07 – Operator lens: unit economics & property differentiation 21:14 – AI as necessity, not novelty 24:11 – LLMs & the future of search and booking 25:26 – Booking.com on AI search & the Connected Trip 28:08 – Will OTAs lose to ChatGPT? Industry debate 37:53 – “Data is the new marketing” 39:40 – How any PM can start using LLMs today 41:08 – Direct bookings vs OTAs in an AI‑driven world 47:02 – Brand, trust signals & how AI will ‘choose’ you 47:43 – Brand from the operator side 56:10 – Operational excellence as brand 59:37 – From hype to agentic AI: what’s coming next 1:03:38 – Where AI will help most (and where it shouldn’t) 🧡 About Hostaway 🧡 Hostaway is an All-in-One vacation rental software solution for growing property managers. We provide tools to automate and simplify marketing, sales, communication, operations, reporting and accounting. Our software is different from every other PMS and Channel Manager, because it is flexible and grows with your business. It’s customizable and we provide an amazing team that helps you set it up and cheer you along your path to success. Hostaway is also the largest marketplace for vacation rental software and tools. Our Marketplace features over 100 solutions and our team can recommend you solutions to every imaginable problem. Hostaway is privately owned and funded by a comprehensive network of VC’s and entrepreneurs.