The future of STR: How AI agents are revolutionizing property management

The short-term rental industry stands at a pivotal crossroads as artificial intelligence moves from marketing buzzword to operational reality. Ahead of IMN's Short Term Rental Summer Forum, we sat down with Jan Sahagun, Co-Founder of Trellis. Sahagun shared his vision for how AI-native systems will fundamentally reshape the industry—moving it from fragmented, human-dependent operations to software-enforced reliability that rivals traditional hospitality.

From system of record to system of action

The distinction between traditional property management software and truly AI-native platforms isn't just semantic—it's architectural. While legacy systems function as databases that track information, AI-native platforms are built on what Sahagun calls a "unified data layer" that enables agents to execute operations, not just monitor them.

This shift represents a fundamental reimagining of STR operations. Rather than running fixed workflows, AI agents maintain a live model of the business and continuously reschedule work as conditions change. They're self-improving systems where every error and edge case feeds back into better workflows and data models, producing increasingly sophisticated behavior over time.

The roadmap to AI-native operations

For operators looking to transition from traditional systems to AI-native platforms, Sahagun outlines a clear progression path:

• Unify the data: Consolidate all operational information into a single layer.
• Establish operational discipline: Make the business "queryable" by logging every call, message, and task as structured events.
• Codify SOPs into workflows: Transform procedures, from early check-ins to damage claims, into software that agents can execute 24/7.
• Close the loops: Start with high-frequency, well-defined processes like dry cleaning dispatch, guest updates, and damage claims.
• Expand to orchestration: Give agents access to live operational state so they can schedule, reprioritize, and follow up continuously across multiple tasks simultaneously.
• Redirect human talent: Once operations run autonomously, focus people on hospitality design, guest experience enhancement, upsells, brand building, and portfolio growth.

From Uber to Waymo: The guest experience revolution

Perhaps the most compelling aspect of Sahagun's vision is how AI-native operations will transform the guest experience. He draws a powerful analogy: today's STR industry operates like Uber, a marketplace coordinating fragmented supply where quality varies widely and platforms only discover problems after guests complain.

AI-native operations, by contrast, will function like Waymo, with execution controlled end-to-end, making quality a software problem rather than a people problem. For guests, this means nothing falls through the cracks, service is proactive, consistency is hotel-grade, and personalization is programmable.

The 2030 Vision: Who will own the trust layer?

Looking ahead, Sahagun sees a fundamental power shift in the STR ecosystem. While OTAs like Airbnb control discovery and booking, they don't control the operations that determine actual guest experience—the cleaners, maintenance, linens, access, and issue resolution.

This shift will enable market consolidation, allowing operators currently stuck at 50 listings to scale cleanly through software-enforced operations. It will create a federation of property management brands where experience is designed by humans but ensured by software, with shared best practices and guest intelligence across networks.

Want to learn more about how AI-native operations are transforming short-term rentals? Connect with the Trellis team at IMN's Short Term Rental Summer Forum, June 23-24, 2026 in Carlsbad, California.