A guest books. You send a message. Another guest books. You send the same message. Then again. And again. If you are typing that message from scratch every time, you are not running a business — you are running a copy-paste operation that will exhaust you by month three.
Both Airbnb and VRBO have built-in automated messaging tools. They are free, they are built into the platform, and most hosts never fully use them. Here is the full sequence and what each message needs to accomplish.
Why Automated Messaging Matters
Consistent messaging does three things. It sets expectations before the guest arrives, reducing the chance of a misunderstanding that becomes a bad review. It documents your communication on the platform, which matters if you ever need to file a damage claim or dispute a review. And it frees you from having to think about guest communication on a per-booking basis.
A guest who gets a warm, clear message at every stage of their booking feels taken care of without you being present. That feeling is what earns five-star reviews.
The Message Sequence
Every STR host needs six automated messages. Each fires at a different trigger point in the booking timeline. Together they cover the guest relationship from first contact to review.
1. Booking Confirmation
TriggerImmediately after booking is confirmed
Welcome the guest, confirm the dates, and set the tone. This is their first impression of you as a host. Keep it warm and brief. Include your house rules reminder and your pre-arrival requirements — guest count confirmation, ID, dogs.
This is also where you send your screening message if you have not already done so during the request phase.
2. Pre-Arrival
Trigger3–5 days before check-in
This message does the heavy lifting. Include: check-in time, exact address and directions, smart lock code, parking instructions, WiFi network and password, and anything property-specific they need to know before they arrive.
A guest who has everything they need before they arrive does not have to contact you at 4 PM on check-in day when you are unavailable. That is the point.
3. Check-In Day
TriggerMorning of check-in
Short and practical. Confirm the smart lock code, remind them of check-in time, and let them know you are available if anything comes up. This message reassures the guest on the day of travel — when anxiety is highest — that everything is in order.
4. Mid-Stay Check-In
TriggerDay 2 of the stay (or midpoint for longer stays)
Ask how everything is going. This is not a formality. A guest who has a minor issue and does not mention it will mention it in their review. A mid-stay check-in gives them a low-friction opportunity to flag something you can fix before checkout.
A problem you resolve during the stay is rarely a problem in the review. A problem you never knew about always is.
5. Checkout Reminder
TriggerEvening before or morning of checkout
Confirm checkout time. List your checkout requirements: lock the door, start the dishwasher, take the trash out, return keys to the lockbox if applicable. Keep it friendly. This message sets up a clean turnover and reduces the chance of a late checkout that throws off your cleaner.
Setting It Up: Airbnb vs. VRBO
Airbnb calls these Scheduled Messages and they are found under your hosting tools. You can set triggers based on booking confirmation, check-in, and checkout, with offsets in hours or days. Airbnb also supports shortcodes for guest name, check-in date, checkout date, and property name — use them. A message that starts with the guest’s first name is warmer than one that does not.
VRBO offers similar automation under Messaging Templates. The trigger options are comparable but the shortcode library differs slightly. Set up your templates separately for each platform — do not assume the same message works identically on both.
One Rule for Both Platforms
Keep all guest communication on the platform. Do not move conversations to text, email, or any channel outside the OTA. On-platform communication is timestamped and documented. Off-platform communication gives you nothing to stand on if something goes wrong.
Build the Full System
Automated messaging is one layer of a complete host operation. The screening process, turnover documentation, and review strategy complete the picture.
About the Authors
We’re the hosts behind Toccoa Currents, two dog-friendly cabins on the Toccoa River in Suches, Georgia. Our full guest message sequence runs automatically across both properties on both platforms.
Through Drift Currents we offer host services, curated items, a vendor directory, and regional affiliate pages for hosts at every stage.
This post is part of STR Host Guide: Scout. Setup. Stay. Stream. Coming soon on Amazon.