AI Chatbots in Short-Term Rentals: VRBO & Guesty Launch AI Features

Artificial intelligence is quickly becoming a key part of the short-term rental experience for hosts and guests.

Hostaway's CEO made a bold statement in their STR industry report earlier this year: "Those who don't take the time to deeply understand, adopt, and deploy AI will go out of business in five years." He may have a point. Major players in the STR industry are integrating AI into their core operations, and fast.

VRBO unveiled its AI chatbot strategy with impressive early results. And Guesty launched a suite of new AI features, including ReplyAI Autopilot and AI Task Creation.

VRBO's Smart Approach: 1.3 Million Questions Answered in Weeks

Instead of building a complicated booking agent that handles everything from search to checkout, VRBO built a simple Q&A chatbot that lives on the listing page.

The AI reads the listing description, amenities, reviews, and property details. When a traveler asks a question, the system answers instantly right there on the page. The host never gets a notification. The guest does not wait for a reply. It is not a host add-on. It is a core part of the search experience on VRBO.

In its first few weeks, this tool answered 1.3 million traveler questions.

Advice to Companies & Hosts Adopting AI: Start Internally First

Before the VRBO news landed, a panel at the Short Stay Summit shared strategies and lessons on how we should (and should not) adopt AI in short-term rentals.

Steve Schwab, CEO of Casago and Vacasa, pointed out that most of the industry noise around AI has been focused on guest-facing chatbots and trip-planning tools. Those, he said, have consistently underperformed.

His take: The real wins are happening internally.

Schwab explained that smaller operators and hosts can now afford business intelligence tools that were once exclusive to enterprise operators. Those tools need to help improve internal operations, not just guest communication.

Before you point AI outward at your guests, point it inward at your operations. According to him, that's where the real profit margin lives.

And Guesty did exactly that, ticking both boxes for internal operations and guest-facing AI features in their latest AI tool update.

Guesty's New Reply AI Launch & Features: Proactive Operations Inside the PMS

Guesty just launched a suite of new AI features designed to streamline operations and reduce manual work for hosts and property managers.

Here are two features that we know about so far:

ReplyAI Autopilot

This feature automatically handles guest messages across the entire booking lifecycle. It does not just respond to simple questions. It proactively sends check-in instructions, checkout reminders, and post-stay review requests. The cool part? The AI adapts to your property's specific tone and voice, so guests get consistent, on-brand communication without you typing a word.

AI Task Creation

This feature turns conversations and booking events into ready-to-assign tasks. If a guest asks for early check-in, the AI can automatically create a task for your cleaning team. If a maintenance issue comes up, the system flags it and assigns the job. No more manually tracking requests across spreadsheets or text messages.

Both features work inside Guesty's existing PMS, meaning hosts can automate communication and task management without switching between multiple tools.

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What This Means for Hosts

The industry is moving in two directions at once. OTAs like VRBO are using AI to reshape how guests find and book properties. Meanwhile, platforms like Guesty are using AI to help hosts run their businesses with less friction.

If you rely on OTAs for bookings or have built your own direct booking website, know that conversational search is coming. Listings that answer guest questions clearly will likely perform better in AI-driven search results.

If you manage multiple properties, the internal wins are even bigger. AI that handles guest messages and creates tasks for your team can save hours every week. And as Schwab noted, those margin improvements add up fast.

The Bigger Picture: AI Adoption Is Accelerating Fast

Using AI in short-term rentals is becoming the norm. According to the 2026 Industry Report by Hostaway, AI adoption among STR operators leaped to 60.7% in 2025, up from just 46% in 2023. For large-scale managers with 50+ properties, that number soars to nearly 80%.

The report also found that 43% of operators now save at least 2 hours per week using AI—double last year's number. For big teams, those savings translate into real cash, with over 25% of large managers reporting weekly cost savings over $1,000.

How to use AI for your Airbnb: Start Slow, But Start.

Adopting AI isn't about riding the hype train as quickly as possible. It's about choosing tools that work for your business, give you time back, and help you maximize revenue. Start slow. Don't waste time and resources trying everything. Find the tools that help you with the tasks you struggle with the most. It's better to use one tool well than seven tools that yield no results.

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