Airbnb automated messages: the six-message sequence I run from booking confirmation to checkout

My first year of hosting I wrote every guest message individually. A personalised welcome. A thoughtful check-in guide. A mid-stay message that I genuinely crafted for each booking. It felt like good hosting. It also cost me about 25 minutes per booking, which across 90-odd turnovers a year added up to 37 hours of messaging. A full working week.

I automated most of it in early 2023. Kept the personalisation where it actually matters. Cut the messaging time to under five minutes per booking. Guest review scores went up, not down, because the messages went out consistently and on time rather than whenever I happened to be near my phone.

The six-message sequence

Message 1: Booking confirmation (sends immediately)

This goes out automatically when a booking confirms. It does three things: welcomes the guest by name, confirms the key check-in details (address, what to do if they arrive after a certain time), and gives them my direct contact number for genuine emergencies.

The opener is the only part I customise manually, and I do it within the first hour. If someone's profile says they're visiting from Paris, I write one line — "Hope you had a smooth journey from Paris" — and leave everything else as the template. That personal line is the difference between a welcome message that feels like an automated response and one that feels like a person. The rest of the template does the practical work.

Message 2: Pre-arrival detail (sends 5 days before check-in)

Five days out is late enough to be relevant but early enough that guests can make decisions about what to pack or book. This message covers the specifics: how to find the flat, where to park if relevant, the door code or key safe details, what's in the kitchen, and any quirks of the property that I want guests to know about before they arrive.

The Edinburgh flat has a front door that sticks slightly in wet weather. I mention this. The Lake District cottage has a gate that needs lifting as well as unlatching. I mention this. These details turn what would be a 10pm message from a frustrated guest into a non-event. The message is long — maybe 300 words — but every word is there because its absence would create a question.

Message 3: Day-before check-in reminder (sends at 10am the day before arrival)

Short. Four lines. Confirms check-in time, confirms the door code or collection instructions, says I'm available if they need anything, and mentions parking once more if relevant. Nothing that isn't in message 2. But guests who book months ahead often don't re-read message 2. This reminder catches them before they're in the car.

Message 4: Check-in day (sends at 2pm on check-in day)

By this point the guest is either already at the property or very close. This message is the shortest in the sequence. "Hope you've arrived safely. Everything you need is in the flat. Please message me if anything isn't right." That's essentially it. I add one local recommendation — a specific place, not a vague suggestion. "The chippy on Western Road stays open until 11pm and the haddock is worth it" is more useful than "there are great restaurants nearby."

The recommendation always gets a reply. Which is useful, because it opens a conversation that sometimes surfaces small issues before they turn into review comments.

Message 5: Mid-stay check (sends 48 hours before checkout, on stays of 4 nights or more)

I only send this on bookings of four nights or longer. For a two-night stay, a mid-stay message feels intrusive. For a week-long stay, it's a natural midpoint to check in.

It asks one question: "Is everything working as it should?" That's it. Not "How are you enjoying your stay?" which sounds like a review solicitation, and not "Let me know if you need anything" which is vague. A direct question gets a direct answer. And the answers are useful — I've caught a failing shower pressure, a faulty heating timer, and a WiFi issue before they became review comments, all because a guest answered the mid-stay message rather than saving it for the review.

Message 6: Checkout reminder (sends the evening before checkout)

Checkout time, specific instructions, and a thank-you. The instructions are the same three lines I have in the house rules: dishes in the dishwasher, used towels in the bath, food out of the fridge. Saying them again here means guests have them fresh in mind for the morning rather than having to go back and find the check-in guide.

I also say — and this took me a while to add — that they're welcome to leave any leftover food, wine, or toiletries they don't want to travel with, for the next guests. This one line generates a surprising amount of goodwill. I've had checkout messages from guests saying they've left half a bottle of Rioja and some nice coffee. The next guests usually mention it. Nobody's asked for a discount because of it.

What I don't send

I don't send a review solicitation message. Airbnb prompts guests to leave a review — I don't need to pile on. I found that asking for a review made the request feel transactional, and some guests found it slightly uncomfortable. The mid-stay message does more to nudge positive reviews than any direct ask, because it surfaces problems while there's still time to fix them.

I also don't send a "hope you have a wonderful stay" type message at the start and end. These are filler. Guests don't need to be told to have a nice time. They need accurate information when it's relevant.

The rule: personalise the first line, automate the rest

The only thing I do manually for every booking is the first line of the confirmation message. One sentence, written within an hour of the booking confirming, that acknowledges something specific about the guest or their trip. Everything else runs automatically.

This is a meaningful distinction. A fully automated sequence with no personalisation reads like a booking system. A personal opening followed by a useful template reads like a person who's organised. The guest experience of both is similar in practical terms — they get the same information at the same times — but the perception is very different.

Guests who've felt acknowledged at the start are more likely to message me if something goes wrong rather than quietly leaving a three-star review. That's the real value of the first line. Not warmth for its own sake. Relationship infrastructure.

The tool I use

Airbnb has a scheduled messages feature built into the host tools that lets you set up templates triggered by booking events and time windows. It's not perfect — the trigger options are limited and you can't do conditional logic like "only send if booking is more than X nights" without doing it manually — but it handles messages 1, 3, 4, and 6 completely automatically. Messages 2 and 5 I still send manually but from saved templates, which takes about 30 seconds per booking.

If you're managing more than a couple of properties, a proper property management system will give you better scheduling logic and multi-platform sending. But for five properties across Airbnb only, the built-in tool is enough.