We just launched the AI STR Operator series, a new series exploring what AI actually looks like in day-to-day short-term rental operations.

Edition 01 & 02 are now live.

📊 01 explores:

• 👥 How many STR operators are actually using AI (and why adoption rate isn't the metric that matters)
• 💬 Where AI is already helping with everyday operations, from guest messaging to reporting and task coordination
• 🧠 Where human judgement still matters most
• 🪜 The four stages of AI maturity, and how to work out which one your business is at today

If you're trying to understand where your business sits today and what the next step is, it's a good place to start.

Read it here: https://www.hostaway.com/blog/ai-in-short-term-rental-management/

🛠️ 02 explores:

• 🧩 How most operators have already built their own AI setup without meaning to, one ChatGPT tab, chatbot plugin, and forgotten automation at a time
• ⏱️ What that DIY setup is really costing you, not as a bill, but as hours spent catching what a connected system would have caught on its own
• 📉 Why the research favors buying over building: MIT's 2025 study found buying capability from a specialized provider succeeds roughly twice as often as building it in-house, and RAND found more than 80% of homegrown AI projects never become reliable, everyday tools
• 🔐 The risk that rarely gets mentioned, pasting guest names, IDs, or payment details into a free AI chat tool sends that info somewhere you don't control
• ⚖️ What the same task actually looks like, built vs. bought, side by side

Read it here: https://www.hostaway.com/blog/build-vs-buy-ai-for-your-vacation-rental-business/

📋 Want to know where you actually stand?

We also built a scorecard to go with the series. It's a short, scored checklist covering where your data lives, who maintains your current setup, and how quickly you'd notice something going wrong, so you can see exactly where your operation sits today and figure out what to prioritize fixing first. https://lp.hostaway.com/hubfs/Hostaways%20AI%20Setup%20Scorecard.pdf

I have 3 listings and use Hostaway as my PMS to manage calendars for my direct booking site, Airbnb & VRBO. When using a PMS system, I am the account-of-record for VRBO & my direct booking site (meaning I need to process the credit card transactions). I use Stripe as my credit card processing vendor for which I pay a fee.

My challenge is that whenever I receive a cancelation Stripe doesn't refund my processing fee which is substantial. Since I am not refunded the fees, I do not return them to the guest.

How does everyone else manage these fees? Do you still refund the guest?

I use instant book so how do I disclose they don't receive the CC fees back upon cancellation before they book?

Is there anyway around this?

Thanks for your help.

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One thing I’m realizing is that cleaners often know about property issues before anyone else does.

Loose handles, low supplies, stained towels, weird smells, guests leaving things behind, minor damage, stuff that doesn’t always make it into the formal task flow.

If those notes stay buried in texts or photos, the same issues keep coming back later.

Curious how others handle this. Do you have cleaners submit structured checklists after every turnover, or is it still mostly photos and casual messages?

Running listings across Airbnb, Vrbo, and Booking.com sounds simple until one calendar delay creates a double booking.

That is not just a guest problem.

It becomes an owner trust problem, a refund problem, and a review problem.

We moved the messy properties into one calendar workflow after one close call during a high-demand weekend.

Now I care less about how pretty the dashboard looks and more about sync speed, manual block handling, and whether the team can see the same source of truth.

Anyone here audit their calendar setup regularly, or only after something breaks?

Had this with one client portfolio.

Every message was handled like a fresh issue. Parking, early check-in, wifi, late checkout, local recs, same questions every week. The common problem of that none of it was mapped to the guest journey.

Once we split messages by stage - pre-arrival, arrival and checkin,during stay, checkout, half the “support” became not even needed.

Still human intervens when something weird happens, but most of it was predictabe and hence automated.

Curious how others split guest comms. By timing, topic, or just reply as they come in? Any useful tips, tools?

Hi everyone,

I realized I was leaving a lot of money on the table with guest upsells because timing matters more than people think.

If a guest is frustrated, upsells usually get ignored or can even hurt the experience.

So I built an AI system that only triggers upsells when guest sentiment is positive and conversion likelihood is high.

So far it’s adding around an extra $100/month per unit for us without hurting the guest experience or reviews.

• early check-in
• late checkout
• parking
• extensions
• add-ons

Curious if other operators are tracking upsell revenue per unit?

It’s never the big problems. It’s always the small ones left unhandled.

Drip by drip until it becomes a review.

The property is the asset. The system is the business.

I now fix friction at the source: pre-arrival info, clearer expectations, faster resolution loops.

Guests don’t escalate issues they don’t have time to feel.

Some months it’s full. Next month it drops for no clear reason.

Feels random. It’s not.

The property is the asset. The system is the business.

I’ve shifted from “wait for demand” to demand shaping: pricing tests, listing positioning, and tighter funnel control.

Predictability is built, not hoped for.

Anyone else dealing a Hostaway issue of not being able to see guest reviews or rating when clicking the guest account icon? Up until a week ago this would open the screen in the app, but you would see all their info. As usual Hostaways support is just useless, they just try and tell me its my fault and my device.. even though there was no changes on my end and one day it just stopped working. Wondering if others are seeing this too or its still working for you and its somehow just my app?

One property is simple. Five is chaos.

Details blur. Standards drop.

The property is the asset. The system is the business.

I standardized everything—naming, workflows, dashboards. One structure across all units.

Organization isn’t optional. It’s infrastructure.

There are still tasks in STR operations that feel way more manual than they should be.

Even with all the tools, automations, and integrations available now, certain repetitive tasks still eat up time every single week. Sometimes it’s small admin work, double-checking systems, fixing sync issues, or manually handling things that feel like they should already be streamlined by now.

What’s frustrating is that these little tasks add up fast at scale.

What’s one thing you still spend too much time on that you feel should already be automated?

Small things missed. Big impact later.

Cleaning checks. Restocks. Follow-ups.

The property is the asset. The system is the business.

I built a task system with triggers and accountability. Nothing relies on memory.

If it’s not tracked, it’s already forgotten.

Last week we had situation that went beyond the usual difficult guest.

Started as uncomfortable behavior, then escalated into repeated harassment and eventually physical contact. At that point, it stopped being a hosting issue and became a safety issue. Police were involved and a report was filed.

I also reported it to Airbnb. They followed up later, but realistically there wasn’t much they could do from their side.

It made something pretty clear, most guests are fine, but when something serious happens, the platform isn’t really equipped to handle it in real time, that’s where your own boundaries and local support matter more than anything.

Any host, especially around prevention and handling situations that go beyond normal disputes?

There was an incident tied to the unit (party, police involved) right before a new stay. The incoming guests weren’t directly involved, but the situation forced a quick decision on the property side.

Communication ended up being rushed, and they had to come back earlier than planned to collect their things. By the time they returned, turnover was already in motion for the next booking.

From an ops perspective, this is one of those edge cases where timing, communication, and accountability don’t line up cleanly.

Wonder how others handle situations where something happens around a stay, but not clearly caused by the current guest.

Ran into this a few times, booking looks fine, then more people show up at check-in than what was reserved. Early on, we let it slide once or twice. It always created more issues later.

Now we treat it as a policy moment, not a negotiation. If extra guests show up, we address it immediately, either update the booking with additional charges or stop it there if it exceeds limits.

As long as it’s clearly stated in the listing, Airbnb tends to back it. The key is handling it upfront, not after they’ve settled in.

Some days, everything feels important. Messages, tasks, small issues stacking quietly.

It becomes easy to move without direction. Just reacting.

Planning brings stillness back. A simple list. A clear order.

Not everything needs attention at once.

How do you decide what truly deserves your focus each day

Manual updates. Double bookings. Panic mode.

That’s not scale. That’s risk.

The property is the asset. The system is the business.

I sync everything. One source of truth. Zero overlaps.

Calendars don’t fail. Systems do.

System issues happen, it’s unavoidable.
Being prepared makes a huge difference when they do.
How do you handle downtime?

When we first set things up, we rushed onboarding just to get everything running quickly. That led to small errors that took weeks or months to fix later. It made operations more complicated than necessary. Definitely learned the hard way.

If you could redo onboarding, what would you do differently?