We Analyzed 10,000 Hostaway Guest Messages — These Are the 15 Questions AI Handles Every Day

The Data Behind Guest Messaging

Every property manager suspects it, but few have seen the numbers. The vast majority of guest messages aren't unique situations requiring creative problem-solving. They're the same questions, asked in slightly different ways, dozens of times per week across your portfolio.

We analyzed 10,000 guest messages processed through Hostaway across portfolios ranging from 8 to 150 properties. The results were striking but not surprising: 70% of all messages fall into just 15 categories. The remaining 30% include genuine edge cases, complaints, and booking inquiries that benefit from a human touch.

The implication is significant. If you're managing 20 properties and spending 3 hours a day on guest messaging, roughly 2 hours of that time is spent answering the same 15 questions on repeat. That's time you could redirect toward revenue-generating activities — pricing optimization, new listing acquisition, or guest experience improvements that actually drive reviews.

The 15 Questions and Their Frequency

Here's the breakdown, ranked by volume. Each percentage represents its share of total inbound messages across the dataset.

1. WiFi Password (12.4%)

The single most common guest message. It arrives within 30 minutes of check-in almost without exception. Guests ask for it even when it's posted on the fridge, printed in the welcome guide, and included in the check-in instructions. The phrasing varies — "What's the WiFi?", "Internet not working", "Can't find the network name" — but the intent is identical every time.

How AI handles it: Guestar stores the network name and password in your property knowledge base and delivers it instantly. If the guest says "WiFi isn't working," the AI provides the credentials first and troubleshooting steps second — matching the order a good host would follow.

2. Check-In Time and Process (9.8%)

This includes questions about the exact check-in time, where to find the key or lockbox, access codes, and step-by-step entry instructions. These messages often arrive 24–48 hours before arrival and again on the day of check-in.

How AI handles it: The AI pulls the check-in time from the PMS reservation data and combines it with your property-specific entry instructions from the knowledge base. Dynamic lock codes are delivered in real time — not a stale code from a previous guest.

3. Parking Instructions (8.2%)

"Where do I park?" is the third most common question. For urban properties, this extends to "Is there a garage code?" and "How much does street parking cost?" For rural properties, it's usually "Which driveway is ours?"

How AI handles it: Property-specific parking details — location, codes, restrictions, costs — are stored in the KB. The AI delivers the exact parking situation for that property, not a generic response.

4. Early Check-In Requests (7.1%)

Guests arriving on morning flights or driving long distances frequently ask if they can check in before the standard time. This is both a support question and a revenue opportunity.

How AI handles it: Guestar checks the calendar via Hostaway to determine if the property is available before the scheduled check-in. If it is, the AI can either confirm early access or offer it as a paid upsell — automatically, without you lifting a finger.

5. Late Checkout Requests (6.3%)

The mirror of early check-in. Guests ask on their final morning whether they can stay a few extra hours. The window to respond is tight — if you don't answer within 30 minutes, the guest has already packed up and the upsell is lost.

How AI handles it: Same calendar check. If no same-day arrival is booked, the AI can offer a late checkout for a fee you've predefined. Revenue that would otherwise evaporate while you're asleep or busy with another property.

6. Pet Policy (5.4%)

"Do you allow dogs?" is the sixth most common message. Guests ask before booking, after booking, and sometimes after they've already arrived with the dog. The policy varies by property, making template responses unreliable.

How AI handles it: Each property's pet policy — allowed/not allowed, size limits, fees, restricted breeds — is stored in the KB. The AI delivers the specific policy for that property and can mention pet fees if applicable.

7. Directions to the Beach / Nearby Attractions (4.6%)

Guests want specific walking directions, distance estimates, and insider tips. "How far is the beach?" followed by "Which beach do you recommend?" is a common two-message pattern.

How AI handles it: Your curated local recommendations — distances, walking routes, hidden spots — are served from the KB. This is where AI outperforms a printed guide, because it can respond conversationally and answer follow-up questions.

8. Pool / Hot Tub Hours and Rules (3.8%)

Seasonal properties with pools get this question constantly. "Is the pool heated?", "What time does the pool close?", "Can we use the hot tub after 10pm?"

How AI handles it: Pool and hot tub details — hours, heating status, rules, seasonal availability — are pulled from the KB and delivered instantly.

9. Key / Lockbox Issues (3.2%)

"The code isn't working" or "I can't find the lockbox." These are high-urgency messages that often arrive late at night. A slow response here directly impacts the guest's first impression of the stay.

How AI handles it: The AI delivers step-by-step lockbox instructions with specific location details. If the code is dynamic, it pulls the current code from the PMS. If troubleshooting fails, it escalates to the host immediately rather than leaving the guest stranded.

10. Checkout Process (2.9%)

"What do we need to do before checkout?" — including trash, dishes, towels, key return, and thermostat settings. Guests ask this on their last evening or morning.

How AI handles it: Your checkout checklist is served from the KB — clear, specific, and in the guest's language. No ambiguity about whether they need to strip the beds or start the dishwasher.

11. Restaurant Recommendations (2.5%)

Guests want your personal picks, not a Yelp search. "Where should we eat tonight?" or "Best place for seafood nearby?" These are relationship-building moments that drive 5-star reviews.

How AI handles it: Your curated restaurant list — categorized by cuisine, price, distance, and occasion — is served conversationally. The AI can tailor recommendations based on follow-up preferences ("something kid-friendly" or "romantic dinner").

12. Cleaning Schedule (2.1%)

Long-stay guests ask about mid-stay cleanings. Short-stay guests ask about towel replacements. Both want to know if someone will be entering the property during their stay.

How AI handles it: Cleaning schedules and mid-stay service policies are stored per property. The AI delivers the schedule and can offer additional cleanings as a paid add-on.

13. Noise and Quiet Hours (1.8%)

"What time is quiet hours?" or "Is there a noise policy?" Common in condo or HOA-governed properties where violations have real consequences.

How AI handles it: Noise policies, quiet hours, and HOA rules specific to each property are served from the KB — protecting you from complaints and fines.

14. Heating / AC / Thermostat (1.7%)

"How do I turn on the AC?" and "The heater isn't working" are near-identical in frequency. Smart thermostats like Nest and Ecobee generate more questions than traditional units because guests don't want to download another app.

How AI handles it: Guestar stores appliance-specific instructions — including the make and model of your thermostat — and walks guests through operation step by step. No generic "adjust the thermostat" responses.

15. Grocery Stores and Essentials (1.2%)

"Where's the nearest grocery store?" and "Is there a pharmacy nearby?" round out the top 15. Guests arriving late or unfamiliar with the area ask this within hours of check-in.

How AI handles it: Nearby essential services — grocery stores, pharmacies, gas stations, hardware stores — with distances and hours are served from your local recommendations in the KB.

The Response Time Gap

Across the dataset, the average manual response time for these 15 question types was 47 minutes. That's the median — meaning half of all responses took even longer. Late-night messages averaged 4.2 hours. Weekend messages averaged 1.8 hours.

With Guestar handling these questions through the Hostaway integration, average response time dropped to under 2 minutes. Not because the AI is faster at typing — because it never sleeps, never gets distracted by another property, and never needs to look up the WiFi password in a spreadsheet.

That 47-minute-to-2-minute reduction directly impacts two things property managers care about: review scores (communication is the most volatile review subcategory on Airbnb) and upsell conversion (early check-in and late checkout requests have a 15-minute response window before the guest gives up).

Why This Matters for Hostaway Users Specifically

Guestar is a certified Hostaway Marketplace partner. That means the integration isn't a workaround or a Zapier chain — it's a direct API connection that pulls reservation data, guest details, and property information in real time. When a guest messages through Airbnb, Booking.com, or VRBO, the message flows through Hostaway into Guestar, gets matched against your property knowledge base, and a response goes back through the same channel — all within 2 minutes.

For property managers already using Hostaway, adding Guestar eliminates the need to hire VAs for messaging, build template libraries, or lose sleep over late-night guest questions. Your knowledge base is the single source of truth. The AI is the delivery mechanism.

Frequently Asked Questions

What happens when a guest asks something outside the top 15?

Guestar handles any question your knowledge base can answer — the top 15 are simply the most frequent. For questions the AI can't answer confidently, it escalates to you rather than guessing. You handle the 30% that needs a human; the AI handles the 70% that doesn't.

Do I need to set up responses for each of these 15 questions individually?

No. You build a single property knowledge base covering your property details — WiFi, parking, check-in, local recommendations, house rules, appliance instructions. Guestar's AI understands natural language and maps guest questions to the right information automatically. No keyword matching, no decision trees.

How does Guestar handle the same question asked in different languages?

Guestar detects the guest's language from their message and responds in kind. Your knowledge base stays in your native language — the AI handles translation and natural phrasing in 100+ languages. A German guest asking "Wie lautet das WLAN-Passwort?" gets the same accurate answer as an English-speaking guest, delivered fluently in German.

Can Guestar automatically upsell early check-in and late checkout?

Yes. When a guest requests early check-in or late checkout, Guestar checks the property calendar via Hostaway. If the property is available, the AI can offer it as a paid upsell at a price you've set — automatically, 24/7. Hosts using this feature report $200–500/month in additional revenue per portfolio.

What's the cost compared to a virtual assistant handling these messages?

A VA costs $15–30/hour and still needs sleep. Guestar costs $8/property/month on the annual plan. For a 20-property portfolio, that's $160/month for 24/7 coverage across all OTA channels — compared to $2,400–4,800/month for a full-time VA who can't respond in 100 languages.