To encourage past guests to rebook directly without being annoying, automate a short sequence. Send a thank-you within a day of checkout. Then send one useful check-in a few days later, and a single rebooking invitation weeks after that. Then stop. Send it by email or SMS you own, with consent and an unsubscribe link. At Boostly, we build this follow-up for hosts.
Key Takeaways
- A three-message sequence with a hard stop is enough: a thank-you, a value-led check-in and one rebooking invitation.
- Airbnb and VRBO restrict steering guests off-platform, so keep OTA inbox messages to genuine service and send rebooking pitches only to contacts who opted in through your own channels.
- Marketing consent matters: GDPR applies to UK and EU guests, the TCPA applies to automated marketing texts in the US, and every marketing message needs a working opt-out.
- Segment by first-time versus repeat guests, season and stay length so each message has a reason to exist.
- Judge results by direct rebookings per campaign, plus unsubscribes and complaints, not by opens alone.
- Boostly’s built-in CRM and automated email and SMS follow-up run this sequence for you, with CRM access within 24 hours of signing up, so past guests return as repeat direct bookings.
Take an illustrative £200 night. A 15% OTA commission on it is £30. A past guest who books again directly keeps that £30 with you. They already know the property and the check-in, so the stay holds no surprises.
In 2026, the hard part is not writing the email. It is collecting contact details legitimately and staying inside platform rules, while sending enough to be remembered without being muted. Most automated messaging advice stops at check-in and checkout. Past-guest win-back is where the gap sits.
At Boostly, we work with a community of over 2,000 short-term rental hosts and operators, and the same pattern keeps appearing: strong OTA listings, almost no owned demand. This guide covers setup, timing, copy, consent and measurement, so you can bring guests back without a pushy campaign.
What Do You Need in Place Before You Automate Past-Guest Messages?
A past-guest messaging system needs three things: contact details you are allowed to use, a place to store them with a record of consent, and a tool that sends on a schedule. Miss any one and automation simply sends the wrong message faster to the wrong people.
The first gap catches most hosts. Airbnb and VRBO typically keep guest contact details inside their own inboxes. Your list has to come from touchpoints you own. These include the checkout page on your direct site, an enquiry form, a sign-up link in your welcome guide, or an in-home WiFi login page. The StayFi WiFi capture system is one example of a tool that collects guest emails that way, with the guest opting in.
Storage is the second gap. A spreadsheet of emails with no source or date makes consent hard to prove, and hand-exported sheets tend to go stale. Boostly’s CRM captures guest records at booking on your direct site instead, and you get CRM access within 24 hours of signing up. The site those guests return to matters too, and our guide on how to build a direct booking website lists what it needs.
Is It Against Airbnb Rules to Message Past Guests About Booking Direct?
Airbnb and VRBO both limit how hosts use their messaging to move guests off-platform, so pitching a direct booking inside an OTA inbox carries account risk. The safer pattern keeps platform messages to service and sends rebooking invitations only through channels the guest opted into.
The exact wording of each platform’s host terms changes, so read the current terms and help centre before you send anything. We are not lawyers, and what follows is practical guidance, not legal advice.
- Inside the OTA inbox: arrival details, a genuine thank-you, a review prompt, and replies to guest questions.
- Outside the OTA inbox: rebooking invitations, perks and newsletters, sent only to guests who gave you their details through your own channels.
- Never: asking a guest to cancel an OTA booking and rebook with you, or sharing payment details to avoid fees.
Boostly is built so you keep your Airbnb listings and let them act as the discovery channel, while your direct site becomes where repeat guests return. Our piece on using a book direct marketplace to drive direct bookings covers another route to direct demand that sits outside OTA inboxes.
How Do I Set Up Automatic Replies and Scheduled Messages in Airbnb?
Airbnb’s scheduled messages are saved templates that you queue against booking events such as confirmation and arrival. You set them up in the messaging settings of your host account. VRBO offers comparable templates and timing in its host tools. Both suit service messages; neither is the place for a rebooking campaign.
Menu names change, so check current help pages. The usual setup is to create a booking confirmation and a pre-arrival note with check-in instructions, then a checkout thank-you, each with the guest’s first name filled in automatically. A property management system (PMS) typically does the same across several platforms from one inbox, with more triggers.
The decision is which message lives where.
| Where the message lives | Best for | Limit |
|---|---|---|
| OTA inbox scheduled messages | Confirmations, arrival details, checkout thank-yous | Platform rules restrict off-platform pitches, and guest contact details stay with the platform |
| PMS messaging | Triggered in-stay messages across several channels from one inbox | Built for operations, so marketing follow-up is usually basic |
| Boostly CRM with email and SMS automation | Past-guest follow-up, repeat booking prompts, availability-aware campaigns | In-stay operational messaging is typically handled in your PMS |
Boostly integrates with 27+ PMS platforms and syncs listings and availability in real time. Pricing stays current too, so a rebooking message never offers dates that are gone. For a wider view of this software category, see our look at where guest services software is heading.
How Do You Set Up an Automated Message Step by Step?
Setting up an automated message means choosing a trigger and writing the copy once. Then you add personalisation fields and define when the sequence stops. The process is the same in any tool. What differs is whether guest data and consent records sit in one place with your sequences, or are scattered across separate tools.
- Capture contacts with consent. Use your direct checkout, an enquiry form or a welcome guide sign-up, and log the date and source.
- Tag each guest. Record stay dates, party type, booking source and consent status.
- Write three messages, not ten. A thank-you, a value check-in and one rebooking invitation.
- Set the triggers. Base each send on the checkout date, with a delay between messages.
- Add a stop rule. End the sequence after the rebooking invitation, and put an unsubscribe link in every marketing email.
- Test it. Send the sequence to your own address and check the name fields, links and send times.
The best email marketing software for vacation rentals is the one that stores stay history and honours opt-outs. It also connects to your booking data. A generic newsletter tool can send, but it will not know who stayed in July or who booked direct.
Boostly’s CRM exists to solve that problem. The CRM holds the guest records, and automated email and SMS campaigns run the follow-up. The templates and AI tools give you a first draft to edit in your own voice, and Boostly maps out the automations with you in a demo.
What Is a Good Rebooking Email Sequence for Past Guests?
A good rebooking email sequence for past guests has a hard stop after two kinds of check-in and one ask: a thank-you and a value-led message, then one rebooking invitation. Extra sends tend to bring unsubscribes and spam complaints, and guests likely to return are usually warm after a single well-timed nudge.
| Step | Suggested timing | Channel | Purpose | Level of ask |
|---|---|---|---|---|
| 1. Thank-you | Within a day of checkout | OTA inbox for OTA stays; email for direct guests | Gratitude and a review prompt | None |
| 2. Value check-in | Roughly 3 to 7 days after checkout | Email to consented contacts | A useful local tip or seasonal update | Soft |
| 3. Rebooking invitation | Roughly 30 to 90 days after checkout | Email; SMS only with explicit consent | One reason to return, with an optional perk | One clear ask |
| 4. Stop | After no response to step 3 | Not applicable | Pause, or move to an occasional seasonal note | None |
Treat those timings as a starting point, not a benchmark, and adjust by season. A guest who stayed in winter might hear from you ahead of next winter, not three months later. Tie step 3 to open dates or an event, not to a calendar reminder.
Boostly’s automated guest follow-up sends pre-set sequences like this one, including repeat booking prompts, so the schedule runs without you opening your inbox. For more off-platform lead generation and email ideas, the Price of Business guide on growing a vacation rental business is a useful companion read.
What Is a Good Message to Send to an Airbnb Guest After Checkout?
A good post-checkout message is short, specific to the stay and makes no demand. It thanks the guest by name and mentions one detail from the trip. The sales pitch waits for a later message sent through a channel the guest opted into.
Message 1, thank-you (OTA inbox or email):
Hi [First name], thanks for staying with us this week. We hope the [specific feature, e.g. woodburner] made the evenings. Safe travels home, and if you have a moment, a review helps other guests find us.
Message 2, value check-in (email, consented contacts only):
Hi [First name], we have just updated our guide to [area] with [seasonal tip]. We thought you might like it. If you ever want to come back, reply to this email and we will help. No reply needed otherwise.
Message 3, rebooking invitation (email):
Hi [First name], [month] dates at [property] are now open. Guests who have stayed before get [perk, e.g. late checkout] when they book on our own site. If the dates suit you, here is the link. If not, no worries. You can unsubscribe below.
Each message gives a reason to read it and makes the next step optional. Our guide to strategic creative communications for bookings goes deeper on tone. Boostly’s templates and AI tools can produce a starting draft, but add your own local detail, because that is what stops it sounding robotic.
How Do You Set Up Automated Messages to Past Guests Without Being Annoying?
Automated messages to past guests feel annoying when they are frequent and generic, or when they are hard to stop. They feel welcome when they arrive rarely, reflect the guest’s real stay and make unsubscribing a single click. A frequency cap and segmentation do most of the work, along with a clear opt-out.
Cap the frequency
Write the cap into the automation: three messages, then a pause. A guest who ignores message 3 should move to an occasional seasonal note or be suppressed, not chased.
Segment before you send
First-time guests need the thank-you and check-in. Repeat guests might get early notice of open dates. Segment by season and length of stay, because a family who stayed a week in August needs a different message than a couple who stayed a weekend in March. Whether they booked direct matters too.
Frame the perk as a benefit
A small perk such as late checkout or a welcome add-on protects your rate better than a blunt discount, and it reads as a thank-you. Boostly’s upsells and add-ons support that kind of offer on your direct site.
Avoid the common mistakes
- Pitching the day after checkout.
- Sending the same copy to every guest.
- Duplicate sends because lists live in two tools.
- Messaging guests who have opted out.
In our experience, duplicate sends are the most avoidable complaint. Keeping segments and send history in one CRM, as Boostly does, removes the cause.
Can I Automate Texts to Past Guests, and What Consent Do I Need?
You can automate texts to past guests, but marketing texts generally need clear prior consent, and the rules differ by region. In the US, the TCPA covers automated marketing texts. GDPR consent applies in the UK and EU, and so do electronic marketing rules. Confirm current requirements for your market before you send.
Separate service messages from promotional ones. A checkout reminder or a note about a lost item is a service message. A perk for next summer is promotional and needs consent behind it. If you are in the UK, the Information Commissioner’s Office publishes guidance on electronic marketing.
Opt-outs deserve the same care as sign-ups:
- Put an unsubscribe link in every marketing email and a clear stop instruction in every marketing text.
- Honour requests quickly and suppress the contact from all future sends.
- Record the date and source of each consent.
Use email as your default and SMS only for guests who asked for it, since texts feel more personal and are more easily resented. Whatever tool you use, keep consent records against each guest record. Boostly’s CRM gives you one guest database to work from. Automated email and SMS campaigns sit on top.
How Do You Track Whether Automated Messages Lead to Direct Rebookings?
Tracking message performance means measuring direct rebookings per campaign, not just opens. The core metrics are the direct rebooking rate among past guests contacted and revenue per campaign. Watch the unsubscribe and complaint rates too, since they show whether you are annoying people.
Here is an illustrative calculation, with assumptions shown. You email 200 past guests, and 4 rebook directly for two nights each at £200 a night. That is £1,600 booked. The same four stays through an OTA at 15% commission would have cost you £240 in fees, which you keep.
Open rates are a weak signal, so treat clicks and bookings as the real numbers. Give each campaign its own tagged link so your analytics can attribute the booking. If unsubscribes climb after a send, cut the frequency before you touch the copy. Tightening the segment comes next.
Most hosts skip this step, which is why Boostly includes analytics and reporting on direct booking performance. You can see direct share and traffic side by side with conversion in one view, rather than guessing which channel earns its keep.
Frequently Asked Questions
Can past guests negotiate the price with me directly?
On your own direct booking site, you set the rates and any perks, so a past guest can ask and you can say yes or no. OTAs generally keep pricing and payment inside their own systems, so check current platform terms before agreeing a price in an OTA inbox. A fixed returning-guest perk is easier to manage than case-by-case haggling.
How many follow-up messages to past guests is too many?
Anything beyond a thank-you and one value check-in is where most hosts start annoying people. The one rebooking invitation is the last message that belongs. After that, pause the guest and move them to an occasional seasonal note, or suppress them if they ignore it. Write the cap into the automation so it does not depend on you remembering.
What is the best timing for a post-checkout rebook message?
Send the thank-you within a day, the check-in a few days later, and the rebooking invitation roughly one to three months after checkout, tied to a season or open dates. A pitch the day after checkout feels premature. Treat these timings as a starting point and test them against your own results.
VRBO’s host tools typically offer message templates and timing options for service messages. Features and menu names change, so check your current dashboard. Use them for thank-yous and review prompts. Keep rebooking invitations for email or SMS to guests who agreed to hear from you.
How do I handle guests who ask not to receive marketing messages?
Remove them from all marketing sequences straight away and record the request. Keep sending genuine service messages for any live booking. Every marketing email should carry an unsubscribe link, and every marketing text should explain how to stop, so the guest never has to ask twice.
What is the best email marketing software for vacation rentals?
Pick software that stores stay history and segments guests. It should also honour opt-outs and connect to your booking data. Boostly’s built-in CRM and automated email and SMS campaigns do this alongside a direct booking site, with CRM access within 24 hours of signing up. Generic newsletter tools can send but will not know who has already booked direct.
How do I stop an automated message sounding robotic?
Use the guest’s first name and mention one real detail from their stay. Keep each message under a short paragraph. Write as you would reply to a friend, and avoid stock phrases. Send the sequence to yourself first, and edit anything you would not say aloud.
What Should You Do Next to Rebook Past Guests Directly?
Automated messages to past guests work when the sequence is short and consented. It also has to be easy to leave. Capture contacts through your own channels, keep OTA inbox messages to service, send one rebooking invitation with an optional perk, and measure direct rebookings per campaign. That is how you encourage them to rebook directly without being annoying. As OTA fees and platform rules keep tightening into 2026 and beyond, an owned list of past guests becomes the cheapest demand you have.
Past guests are your cheapest bookings. Book a Demo with Boostly to see how the built-in CRM and automated follow-up bring them back, while you keep your Airbnb listings. Boostly states: “You will get to 65% direct bookings in a year.” Ask us in the demo how it works for your portfolio.