Most guest problems are information problems, and most information problems are timing problems. The right information delivered at the wrong moment is the same as no information, which is why a structured sequence outperforms answering questions as they arrive.
Message one: at booking
Confirm the booking, thank them, and set expectations for what happens next and when. The specific value here is telling them when they will receive check-in details, which prevents the most common pre-arrival message.
Include anything that would cause a cancellation if discovered later: a steep driveway, stairs, a pet policy, a noise ordinance, a mandatory parking arrangement.
Disclosing friction at booking rather than at arrival is uncomfortable and it is much cheaper than the alternative. A guest who cancels at booking costs you a night you can resell. A guest who arrives and is unhappy costs you a review.
Message two: one week before
Confirm the dates, ask about arrival time, and offer anything that improves the stay: grocery delivery, a restaurant reservation, equipment rental.
This is also where local logistics belong. Where to buy groceries, how long the drive from the airport actually takes, whether a four-wheel drive vehicle is advisable in that season.
The arrival time question has operational value beyond courtesy. It tells your cleaner when the property has to be ready and flags a late arrival before it becomes a problem.
Message three: day before arrival
- The address, with a note about anything a mapping application gets wrong.
- The door code or key arrangement, with a photograph of the entry.
- Parking instructions, specific and with a photograph.
- Wifi network and password.
- The number to call if something goes wrong, and who answers it.
Photographs matter here more than words. A picture of the front door and the parking spot eliminates most arrival confusion, particularly at night in an unfamiliar area.
Message four: shortly after check-in
A brief message asking whether they got in and whether everything is as expected. This is the highest-value message in the sequence.
It surfaces problems while they are still fixable. A guest who mentions a dead lightbulb at 4pm on arrival day gets it fixed and leaves a five star review. The same guest who says nothing writes about it a week later.
Keep it short and make clear you are not expecting a reply if all is well. Guests on vacation do not want a conversation.
Message five: the day before checkout
Checkout time, checkout instructions, and thanks. Keep the instructions minimal.
Long checkout task lists are one of the most common complaints in short-term rental reviews. Guests paid a cleaning fee and being asked to strip beds, run the dishwasher, take out the trash and vacuum reads as a double charge.
Ask for the two or three things that genuinely help the turnover and let the cleaning fee cover the rest.
The review request
A brief message after checkout asking for a review, sent once, with no pressure and nothing offered in exchange.
Guests who had a good stay frequently do not review unless prompted, and review volume matters because it dilutes the weight of any individual bad review and feeds the ranking algorithm.
Ask once. A second request reads as pressure and can produce a worse review than none at all.
Automation without sounding automated
All five messages can be automated on most management platforms, triggered by booking, days before arrival, hours after check-in and days before checkout.
The risk is that automated messages read as automated, which undercuts the trust they are meant to build. Two things fix that: writing them in a natural voice rather than a corporate one, and including specifics that could only apply to your property and market.
A message that says 'the grocery store closest to the cabin is the Food City on the Parkway, about eight minutes down the hill' reads as a person. One that says 'local amenities are available nearby' reads as a template, because it is.
Leave the post-check-in message slightly less polished than the rest. It is the one where guests are most likely to reply with a problem, and a message that reads as a genuine person asking is more likely to get an honest answer than a formatted one.
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Frequently asked questions
What messages should I send Airbnb guests?
Five: booking confirmation with any friction disclosed, a one-week-out message asking arrival time, a day-before message with address, code, parking and wifi, a short post-check-in check, and a day-before-checkout message. Then a single review request.
What is the most valuable guest message?
The short check-in follow-up. It surfaces problems while they are still fixable. A guest who mentions an issue on arrival day gets it fixed and leaves a good review; the same guest who says nothing writes about it later.
Should I ask guests to do checkout tasks?
Keep it to two or three items that genuinely help the turnover. Long checkout task lists are a common review complaint, because guests who paid a cleaning fee experience it as a double charge.