AI and automation are no longer future concepts for vacation rental operators. They are tools that leading property managers are using right now to work smarter, serve guests better, and scale their businesses. But getting started can feel overwhelming, especially with so many platforms, tools, and promises competing for your attention.

During Breezeway’s 2026 ELEVATE Summit, three experienced hospitality professionals, including moderator Heather Bayer and panelists Alex Zemianek and Jessica Grogan shared what is actually working. Here is what they had to say.

What has actually changed for operators using AI

The shift from curiosity to real operational impact

The conversation around AI has moved well beyond content writing and email drafts. Operators who have leaned into it are seeing genuine transformation in how their teams work day-to-day.

Alex Zemianek, CEO of JZ Vacation Rentals, described his journey: "I went down a very deep AI rabbit hole and basically was able to build an agentic system where I can have full software from end to end that now connects to all of the different tech systems we use in our industry. And I don’t have a coding background."

Jessica Grogan, COO of Rent Branson, which manages about 330 properties in the Ozarks, echoed a similar path. Her team focused first on removing the tasks her staff dreaded most, like analyzing invoices and handling repetitive admin work. She asked her team, "What can we get off your plate so that you can focus more on being more hospitable?"

The takeaway: AI adoption does not require a tech background. If you can identify a pain point, you can start building a solution.

Building the right foundation before adding AI tools

Get your house in order first

One of the most consistent themes from all three speakers was this: before you add AI tools, get your foundational knowledge in order. AI amplifies what you give it. If your processes, SOPs, and standards are disorganized, your AI outputs will reflect that.

Alex compared it to a filing system: "The folder system is essentially the brain... I already knew our human folder system, which is our Google Drive, wasn’t the most organized, and we had a lot of work to do. The more that as humans we go to that information faster, the more that our AI can go grab that information and do it very quickly and accurately."

Jessica described how Rent Branson feeds their company culture directly into their AI tools, including their core values and even their annual company word: "We pick a word every year... Our word for this year is obsession. We are obsessed with our guests, obsessed with our owners. And so now, anytime you have a conversation with our AI, it feeds into that obsession."

Here are four practical steps to lay the right groundwork:

1. Document your SOPs before connecting them to any AI tool.
2. Create a shared folder or drive that acts as your AI’s “brain.”
3. Feed your brand voice, tone, and company values into your AI tools.
4. Use tools like Google NotebookLM to make SOPs easily searchable for your whole team.

Breezeway tip: Breezeway’s platform is purpose-built for standards-based operations. Its customizable checklists, task templates, and centralized property data give teams a solid operational foundation that AI tools can build on.

What to automate and where human judgment still wins

Automate the routine. Protect the moments that matter.

Not everything should be automated. The operators who get this right draw a clear line between what AI can handle and where a human touch is non-negotiable.

Jessica broke it down clearly when it comes to guest communication: "For Wi-Fi passwords, basic questions, I want that to be automated. I can teach it my company culture, I can teach it to be hospitable in its voice. But the instant that a guest sentiment changes, I want it escalated. I want my team to be able to be hospitable to those people."

Alex takes a similar approach at JZ Vacation Rentals, using door lock integrations to trigger a human follow-up: "I want to automate when someone enters and then five minutes later, automate a reminder to our head of experience or guest support supervisor to contact the guest. So there’s a human in the loop. We want to be the beginning, we want to be the end, and AI can be everything in between."

Jessica also shared one moment she would never hand off:

"When the guest walks in the front door... we write our guest names on the chalkboard and say, welcome, [insert family name]. That’s something I think we could never take away from them." - Jessica Grogan, COO, Rent Branson

Consider automating:

1. Task scheduling and turnover workflows.
2. Routine guest messages (arrival info, Wi-Fi, check-out reminders).
3. Invoice analysis and administrative tasks.
4. Meeting transcriptions and daily summaries.
5. Maintenance work order routing.

Keep the human touch for:

1. Responding to upset or frustrated guests.
2. Personal welcome moments at check-in.
3. Owner relationship conversations.
4. Handling sensitive guest issues or complaints.
5. Any interaction where tone and empathy are critical.

Breezeway tip: Breezeway’s automated workflows handle scheduling, task routing, and real-time team coordination so your staff can focus on the moments that drive 5-star reviews. Breezeway Messaging consolidates guest communication into one inbox and offers AI-powered suggested replies and sentiment detection, while keeping your team in control of every conversation.

Finding your AI champion

You probably already have this person on your team

One of the most practical insights from the webinar was around finding an internal AI champion, someone who is hungry to learn, eager to experiment, and willing to share what they find with the rest of the team. If you look around your team, that person is probably already there.

Jessica found hers on the maintenance team: "His name is Carl. Carl was critical. Just saying, hey, we can use AI for this. It builds that excitement and takes away the fear factor that a lot of people have around AI and just makes it more normal for everyone."

Alex promoted a team member named Nico, who had already been building API connections between Breezeway and other tools in their tech stack. He put it plainly: "I feel like you need somebody on your team [who really keeps up with it]. It starts at the top. But finding that one person, because of how fast AI moves, you have to have that champion that is willing to keep up and knows how to translate it back to your core operations."

First steps you can take this week

Start small, build from there

All three speakers had advice for operators who want to get started without getting overwhelmed.

Alex’s advice: Start with prompt engineering.

"If you’re new, prompt engineering is everything. If you don’t know where to start, just start by asking the AI, how do I use you? Teach me."

He also recommended committing to one AI tool before trying others, and consuming AI content in small, daily doses to stay current without burning out.

Jessica’s advice: Start with the AI already built into the tools you use.

"So many of the softwares now have AI included in them. Start getting comfortable using the AI that’s already in the softwares you’re already using."

Breezeway is a great place to start. Its automation features for task scheduling, and AI-powered guest messaging are built directly into the platform you may already be using.

Heather’s advice: Go back to your foundations.

"Make sure all your knowledge is in place. Your SOPs, your avatars, your business DNA, your values, all written down in a way that AI can read it."

Key takeaways

Here is what smart operators know about AI and automation:

1. AI adoption does not require a tech background. If you can identify a pain point, you can start solving it.
2. Build your foundation first. Clean up your SOPs, processes, and shared drives before layering in AI tools.
3. Automate the routine. Protect the human moments that drive loyalty and 5-star reviews.
4. Find your internal AI champion. They are probably already on your team.
5. Start with the tools you already have. Many platforms, including Breezeway, already have AI built in.

FAQs about AI in vacation rentals

What is AI automation in vacation rentals?

AI automation in vacation rentals refers to the use of artificial intelligence to handle routine operational tasks such as scheduling cleanings, routing maintenance work orders, sending guest messages, and generating performance reports. It helps property managers save time, reduce manual errors, and maintain consistent standards across their portfolio.

What tasks should vacation rental managers automate first?

Most operators recommend starting with the tasks that are most repetitive and time-consuming. Common first wins include turnover scheduling, arrival and departure guest messages, maintenance work order routing, and invoice processing. Tools like Breezeway can automate many of these tasks directly from your property management system data.

Will AI replace vacation rental staff?

No. The most effective AI strategies in vacation rentals keep humans at the center of key moments, particularly guest check-in, issue resolution, and owner communications. AI handles the behind-the-scenes work so staff can focus on high-impact, high-touch interactions.

How do I start using AI in my vacation rental business?

Start by documenting your SOPs, company values, and operational standards. Then explore the AI features already built into the software you use. As you get comfortable, you can expand into additional tools for communication, scheduling, and reporting. Identifying an internal AI champion on your team can also accelerate adoption.

What AI tools are best for vacation rental operators?

The best AI tools depend on your specific needs. For operations and team coordination, Breezeway offers automated scheduling and AI-powered guest messaging. For general productivity, tools like ChatGPT, Claude, and Google Gemini are widely used. Many operators recommend starting with one tool and learning it thoroughly before expanding.

How does AI improve the guest experience in vacation rentals?

AI can personalize and speed up guest communication, automate arrival and departure messaging, flag unresolved issues for human follow-up, and use property data to make each interaction feel relevant and timely. Breezeway’s messaging tools, for example, use reservation and property data to power automated messages and AI-suggested replies that feel personal, not robotic.

Do I need technical skills to use AI in my vacation rental business?

No. Many AI tools are designed for non-technical users, and starting with AI features built into platforms you already use is a low-barrier way to begin. As Alex Zemianek of JZ Vacation Rentals put it, just about every one of us is now a developer, whether we know it or not.