When AI chat tools first became widely available, one of the most immediate changes we noticed in our short-term rental (STR) business was in how our offshore front desk agents communicated with guests. Their ability to sound more natural—and more American—improved almost overnight. AI became a real-time assistant, helping them parse nuanced guest messages, understand real estate-specific terminology, and troubleshoot problems with greater fluency.
So far, this has been the most ubiquitous application of AI in STR operations: enhancing guest communication. But it’s not without challenges. For one, these AI tools don’t “know” our properties in depth. That means when a guest complains that the hot tub isn’t heating fast enough or the AC isn’t working properly, the response tends to be general and sometimes unhelpful.
Another issue? AI can be overly verbose or emotionally exaggerated. If left unchecked, it churns out responses filled with excessive apologies and platitudes—“We care deeply about your experience and won’t rest until this is resolved”—when what the guest really wants is a straight answer and a solution. Teaching staff how to properly prompt AI tools has become a necessary skill.
Another strong use case for AI is writing listing titles and descriptions. We use a templated prompt that allows us to generate accurate, SEO-optimized listings in minutes. What used to take over an hour can now be completed in under 10 minutes.
Where AI has not yet had a significant impact—but likely will soon—is in two critical areas:
- Revenue Management: Human judgment still plays a central role in setting nightly rates, creating pricing algorithms, and making strategic adjustments based on market feel and experience.
- Vendor Scheduling: Coordinating cleaning crews, maintenance, and mid-stay repairs still requires human oversight. AI simply isn’t ready to handle the complexity, variability, and real-time demands of these logistics.
When those two areas—revenue and operations—are fully supported by AI, we’ll be much closer to a future where technology can run an STR business end-to-end. From my perspective, that future is welcome. It would allow us to reduce personnel needs significantly while maintaining, or even improving, the guest experience.
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