It’s 10:40 at night. A guest has just landed, and they’re asking for the door code.
You sent the door code. Three days ago. In a long message with the wifi password, the parking rules, the bin schedule and a paragraph about the coffee machine. They didn’t read it. Of course they didn’t.
So you type it again, from bed, for the fourth time this week.
Most hosts I talk to send the same six or seven messages to every single guest. Typing them by hand is slow. Automating them badly is worse: guests can smell a robot, and a cold, copy-pasted wall of text makes a stay feel like a transaction.
This post is a practical guide to the middle path. Which messages to put on autopilot, which ones you must never automate, ready-to-copy templates that still sound like a person, and the one rule that keeps AI from embarrassing you.
The messages every stay needs
Almost every short-term rental stay has the same rhythm. Guests need roughly the same information at roughly the same moments:
- Booking confirmation. Right after they book. “Thanks, you’re in, here’s what happens next.”
- Pre-arrival. Two or three days before check-in. Address, check-in time, how to get in, parking.
- Check-in day. The morning of arrival. A short reminder and the door code.
- Mid-stay check. The day after arrival. “Is everything OK?”
- Checkout reminder. The evening before they leave. Checkout time and the few things you need them to do.
- Review request. After checkout. A thank-you and a gentle ask.
These six are predictable, routine and the same for everyone. That’s exactly what automation is good at. Nothing in them needs judgement. They just need to arrive on time, every time, even when you’re asleep, on holiday or dealing with a leaking pipe in another unit.
If you only take one thing from this post: automate these six, and nothing else, at first.
The messages you should never automate
Now the other list. This one matters more.
- Complaints. “The shower is cold.” “It’s dirtier than the photos.” A canned reply here feels like being put on hold.
- Refunds and money. Anything about refunds, extra charges, damage deposits or discounts. These are decisions, not messages.
- Safety issues. A broken lock, a gas smell, a guest who feels unsafe, a medical problem. A human needs to read it and act, now.
- Anything emotional. A guest whose trip was cut short by a family emergency. A honeymoon that isn’t going well. A guest who is clearly upset.
- Anything unusual. A request you’ve never seen before. Bringing a dog. A party “just for a few friends”. An early check-in that clashes with the cleaner’s schedule.
The common thread: these messages need judgement, and the cost of getting them wrong is high. A bad automated welcome message costs you nothing. A bad automated reply to a complaint can cost you a refund, a one-star review, or worse.
A simple test I like: if the wrong reply could cost you money, a review or someone’s safety, a human writes it.
Ready-to-copy templates
Here are the six routine messages, written to be short and warm. Copy them, then change them until they sound like you.
The bits in curly brackets, like {guest_first_name}, are placeholders: slots your messaging tool fills in automatically from the booking. Every tool names them a little differently (Airbnb calls them “details”), so swap mine for whatever yours uses.
1. Booking confirmation
Send: right after the booking is confirmed.
Hi {guest_first_name},
Thanks for booking {listing_name}! You're all set for {check_in_date}.
I'll send you directions and check-in details a few days before you arrive.
In the meantime, is this trip for anything special? Happy to help you plan.
{host_first_name}2. Pre-arrival with check-in info
Send: 3 days before check-in.
Hi {guest_first_name},
Not long now! Here's what you need for {check_in_date}:
Address: {listing_address}
Check-in: from {check_in_time}
Getting in: {check_in_instructions}
Parking: {parking_info}
What time do you think you'll arrive? Then I'll know when to look out for you.
{host_first_name}3. Check-in day
Send: morning of arrival.
Good morning {guest_first_name}!
The place is ready for you from {check_in_time}.
Your door code is {door_code}.
Wifi: {wifi_name} / {wifi_password}
Safe travels. Message me here if anything is unclear.
{host_first_name}Notice the door code is in this message, not only in the pre-arrival one. Guests look for the code on arrival day, so put it in the message they’ll see on arrival day.
4. Mid-stay check
Send: the morning after check-in.
Hi {guest_first_name}, hope you slept well!
Is everything working as it should?
If you're looking for breakfast, {local_tip}.
{host_first_name}5. Checkout reminder
Send: the evening before checkout.
Hi {guest_first_name},
Just a reminder that checkout is tomorrow by {check_out_time}.
Before you go, could you:
- leave the keys {key_return_instructions}
- put used towels in the bathroom
- take any rubbish to {bin_location}
No need to clean anything else. Safe trip home!
{host_first_name}6. Review request
Send: the day after checkout.
Hi {guest_first_name},
Thanks so much for staying with us. I hope you had a great time in {city}.
If you have a minute, a review would really help a small host like me.
And if anything wasn't right, please tell me directly. I'd rather fix it.
{host_first_name}That last line does real work. It gives an unhappy guest a private place to complain before they complain publicly.
How to make them sound human
Templates sound robotic for a few predictable reasons: they’re too long, too formal, and clearly written for nobody in particular. Here’s how to fix that.
Use their name, and yours. “Hi Sarah” and “Tai” at the bottom. Not “Dear Guest” and “The Management”. Every decent tool can fill in the guest’s first name.
Add one local tip. One, not ten. “The bakery two doors down opens at 6 and sells out of croissants by 8.” A real tip from a real person is the single fastest way to stop sounding like a template. Keep a few tips per property and rotate them.
Short sentences. Short messages. If a message needs scrolling on a phone, it’s too long. Split the information across the stay instead: address before arrival, door code on the day, checkout tasks the night before. Each message should do one job.
Ask one question. “What time do you think you’ll arrive?” “Is everything working?” A question invites a reply, and a reply turns a broadcast into a conversation. More than one question and people answer none of them.
Write how you talk. Read the message out loud. If you wouldn’t say it to a guest at the door, rewrite it. “Kindly be advised that checkout is at 11:00” becomes “Checkout is by 11 tomorrow.”
Skip the exclamation-mark storm. One is friendly. Four is a sales email.
Check the timing feels natural. A “good morning” message that lands at 2am in the guest’s time zone gives the game away. Check which time zone your tool uses. Airbnb, for example, sends scheduled messages in the listing’s time zone.
Your options for sending them
There are three broad ways to automate these messages. None is “the best”. It depends on how many units you run and how many platforms you’re on.
Option 1: The platform’s own scheduled messages
If you’re mainly on Airbnb, start here. It’s free and already built in.
At the time of writing (October 2026), Airbnb calls these quick replies and scheduled quick replies. A quick reply is a saved template you can send with a tap. A scheduled quick reply goes out automatically, before or after an event like a new reservation, check-in or checkout. You set them up from Messages, under the quick replies settings.
A few things I found useful in Airbnb’s help pages:
- Templates can include details, Airbnb’s word for placeholders, such as the guest’s first name, check-in time, address, wifi details and house rules. If the listing is missing that information, it shows as unavailable, so fill in your listing properly first.
- For any single booking, you can edit, skip or send now an upcoming scheduled message without changing the template. Very handy when a guest has already asked and you’ve already answered.
- Deleting a template removes all its future unsent messages for every listing that uses it. Edit rather than delete if you’re unsure.
The limit is obvious: it only covers Airbnb. If you also take bookings from Booking.com, your website or WhatsApp, you’re managing several sets of templates in several places.
Option 2: A channel manager or PMS
A channel manager or PMS (property management system) is software that connects to several booking platforms at once and keeps your calendars, bookings and messages in one place. Most of them include message automation.
A few well-known examples, described from their own documentation:
- Hostaway has “message automations”: templates with dynamic fields, triggered by events like a new reservation, arrival, departure or cancellation, and set per channel or per listing. It separates automations from saved templates you send by hand.
- Guesty offers automated messaging built on templates and rules tied to guest actions like check-in and check-out, with custom tags for things like wifi codes and key access.
- Hospitable offers automated messaging across connected platforms from one inbox, plus AI-written replies.
I’m not ranking these. Features and prices change often, and the right choice depends on your size and channels. What matters for this post: they let you write each message once and use it across platforms. Above a handful of units on more than one platform, that alone can save real time.
Option 3: AI-drafted replies
This is the newest option, and the one most likely to go wrong.
Many tools, including some of the ones above, now offer AI that reads a guest’s message and writes a reply. Some can send that reply automatically, without a human looking at it.
AI is genuinely good at drafting. It can read “hi what time can we get in and is there parking” and write a friendly, correct answer from your listing info in two seconds. That’s useful.
But “drafting” and “sending” are two very different jobs. Which brings me to the rule.
The human-approval rule
Here it is, as plainly as I can put it:
For anything that isn’t routine, the AI drafts and the host sends.
The scheduled six (confirmation, pre-arrival, check-in, mid-stay, checkout, review) can go out on their own. You wrote them, you checked them, they’re the same every time.
Everything else, every reply to something a guest actually wrote, gets a human look before it goes out. The AI can write the first draft. You read it, fix it if needed, and press send.
Why so strict? Because of how these AI models work. A language model, the technology behind tools like ChatGPT, predicts likely-sounding text. It’s very good at sounding right. It is not always right. It can:
- Promise things you didn’t agree to. “Sure, early check-in at 10 is no problem!” when your cleaner arrives at 11.
- Invent details. A parking spot that doesn’t exist. A pool that closed last year.
- Miss the tone. A cheerful “Glad you’re enjoying your stay!” in reply to a guest who just said their wallet was stolen.
- Handle the unusual badly. The weirder the message, the more likely the guess is wrong, and the weird messages are exactly the ones that matter most.
I wrote more about this in How to Tell If an AI Product Is Real or Just a Demo: the real question isn’t whether AI makes mistakes, it’s what happens when it does. If the AI sends on its own, its mistakes reach your guest. If you approve first, its mistakes reach you, and you fix them in five seconds.
Here’s an example of how this looks in practice. It’s a made-up one. Imagine Linh, who runs four apartments. A guest writes: “We’re arriving at 9am, can we drop our bags?” Linh’s tool drafts: “Of course! You’re welcome to check in early at 9.” Linh reads it, remembers the cleaner isn’t done until 1pm, and changes it to: “You can leave your bags in the lockbox from 9, and the apartment will be ready by 1.” Five seconds of reading saved a very awkward morning.
That’s the whole point. The AI saves you the typing. You keep the judgement.
A practical way to set this up:
- Automatic: the scheduled six. Write them once, check them, let them run.
- AI drafts, you approve: routine guest questions. Parking, wifi, late arrival, “where’s the nearest supermarket”, early check-in or late checkout requests.
- Always you, from scratch: complaints, refunds, damage, safety, anything emotional, anything you’ve never seen before.
If a tool only offers “fully automatic replies” with no review step, think hard before turning it on. If it does offer a review step, use it, even when it feels slow at first.
What the whole stay looks like
Put it together and every stay follows the same shape:
The top row is the same for every guest. The bottom two rows are where the real hosting happens.
Knowing what needs a reply
Automating the routine messages solves half the problem. The other half is noticing the messages that need you, buried among the “thanks!” and “see you soon” replies across Airbnb, Booking.com and WhatsApp.
That’s a different job from sending. It’s sorting. Some tools help with it inside their inbox. It’s also the job we built Santara around: one morning briefing that, among arrivals, departures and cleaning, lists the guest messages that need a reply, each linked back to where it came from. It doesn’t send anything to guests. The host reads, decides and replies. I explained why in Why Santara Sends One Briefing, Not a Chatbot.
Whatever you use, the principle is the same: let software handle the predictable, and make sure the unpredictable lands in front of a human fast.
How to start this week
You don’t need a new tool to begin. Here’s a simple plan:
- Write your six templates. Start from mine. Make them sound like you. Add one real local tip per property.
- Set them up in what you already have. Airbnb’s scheduled quick replies if you’re mostly on Airbnb, or the automation in your channel manager if you have one.
- Test on yourself. Read each message on your phone, at the time it would arrive. Too long? Cut it.
- Watch the first ten stays. Note which questions guests still ask. Usually it means a message is missing something, or the info is in the wrong message.
- Only then consider AI drafts, and only with a review step.
Most hosts find the first two steps alone save the late-night door-code messages. That’s a good start. As I argued in People Don’t Pay for Features. They Pay to Do Less., the goal isn’t more tools. It’s fewer tasks.
The takeaway
Automate the boring, predictable messages. Six of them cover most stays.
Write them short, warm and personal: their name, your name, one local tip, one question.
Never automate complaints, refunds, safety or anything emotional or unusual.
And when AI writes your replies, follow one rule: the AI drafts, you send. It saves you the typing. You keep the judgement. Your guests will never know the difference, and that’s exactly the point.
Sources: Airbnb Help Centre, “Create scheduled quick replies and send them to guests automatically” (airbnb.com/help/article/2897) and related quick replies articles (2898, 3297); Hostaway Support, “Message Automations” (support.hostaway.com); Guesty for Hosts Help Centre, “Automated Messaging Overview” (help.guestyforhosts.com); Hospitable, “Automating guest communication for short-term rentals” (hospitable.com). Feature names checked October 2026 and may change.
Related: The Real Math of One Airbnb Unit, and AI Won’t Replace Small Business Owners. It Will Replace Their Busywork..
