An email lands: a new booking, deposit paid. It’s a small moment, but it’s the best opportunity you’ll get to turn a one-off guest into someone who books with you directly every year.
With Airbnb or Booking.com, this moment isn’t yours. The platform owns the guest relationship, and its next email to them is often an ad for somewhere else. With a direct booking, the relationship is entirely yours from the first minute. Use it.
Here’s a simple sequence to work through every time.
1. Send a welcome email straight away
Don’t wait. As soon as the booking and deposit come through, send a warm, human welcome message. Keep it plain — a guest wants clarity, not a marketing pitch. Cover:
- Confirmation of their dates and the property
- When the balance is due
- How to pay it
For the balance, you’ve got two simple options:
- Stripe Payment Link — set a reminder and send this from your own Stripe account on the relevant date. Quick for the guest, but Stripe takes a small fee.
- Direct bank transfer — give your account details and ask the guest to pay this way instead. No fees, and most guests are happy to do it for a holiday let.
Either way, tell them clearly rather than leaving them to guess.
2. Point them to house rules and facilities
Ideally this is a page you already have ready to link to — house rules, what’s included, parking, wifi, check-in/check-out times, anything that saves you both a back-and-forth email later. If you haven’t built this yet, it’s worth doing once and reusing it for every guest.
3. Link to your local guide
If you’ve got a blog with local recommendations — walks, beaches, pubs, places to eat — this is exactly the moment to share it. It’s useful to the guest, and it starts positioning your brand as more than just a place to sleep. It’s the beginning of the relationship, not just the booking.
4. Remind them they’ve skipped the noise
Worth saying, gently, somewhere in your welcome material: because they’ve booked direct, they won’t be getting Airbnb or Booking.com emails nudging them towards other properties, discount stays, or “similar homes nearby.” That inbox space is yours alone. It’s a genuine advantage of booking direct — most guests haven’t thought about it, so it doesn’t hurt to point it out.
5. Ask for a phone number now
If phone number isn’t a required field at booking, the welcome email is a good place to ask for it anyway. On arrival day, most guests would rather get a text or WhatsApp message than dig through email — and it means your number is already saved in their phone before they’ve even set off, which is handy if plans change or they get lost on the way. A simple line works fine:
“Happy to text you on arrival day instead of email — what’s the best number for you?“
6. Ask permission for future marketing
This is where the long-term value sits. If you’d like to send this guest offers, seasonal discounts, or early-booking deals down the line, ask — don’t assume. A simple opt-in checkbox or line in the welcome email works:
“Would you like us to email you about returning-guest discounts and seasonal offers? You can unsubscribe any time.”
Transactional emails (booking confirmations, balance reminders, check-in details) don’t need this. Anything promotional does — that’s a straightforward permission-based marketing requirement, not just good manners.
7. Consider teaming up with local suppliers
Once someone’s opted in to hear from you, there’s more you can offer than just your own place. A local taxi firm, a restaurant, a tour operator — arranging a small discount or referral relationship with them gives you something extra to include in guest emails, and it’s a nice way to build goodwill with other local businesses at the same time.
8. Always link back to your site and blog
Every email you send — welcome, balance reminder, check-in info — should have your website and blog linked in the footer. It costs nothing and it keeps reinforcing that this is your brand, not a booking platform’s.
A few more things worth doing
Split the timing. Don’t cram everything into one email. Welcome and payment info goes out immediately; house rules and local guide can follow a few days later; detailed check-in instructions (door codes, parking, key safe) are best sent closer to arrival, so the guest isn’t hunting through old emails for them.
Personalise where you can. Even just using the guest’s name and the property name in each email makes it feel like it’s come from a person, not a system — which, appropriately, it has.
Follow up after the stay. A short thank-you a day or two after checkout, maybe with a request for a review and a small returning-guest discount code, closes the loop nicely. This is often the single highest-converting email in the whole sequence, because they’ve just had a good experience and it’s fresh.
Keep an eye on unpaid balances. If you’re relying on bank transfers, it’s worth a manual check a few days before the balance is due, in case it’s been missed rather than skipped.
Put that phone number to use. Once you’ve got it, a short text with check-in details on the day itself is a good backup to email — some guests won’t check their inbox closely once they’re travelling.
None of this needs to be complicated. A handful of well-timed emails, sent consistently, is what turns a single booking into a guest who comes back — and tells their friends — without ever going near Airbnb or Booking.com again.
