Email Marketing Automation for Vacation Rental Managers: What Actually Works

Every booking through Airbnb costs you 15-20% in commissions.
Every booking on your own site? Zero commission—and you own the guest relationship. 

Email automation is how you build that relationship over time. The right message at the right moment turns a one-time guest into a repeat booker—without you lifting a finger. But most property managers either don’t have the time to set it up, or they’re sending the wrong emails at the wrong time.

This guide covers the email automations that actually move the needle for direct bookings—and what each one should accomplish.

The Guest Journey: 11 emails that matter

The best email programs aren’t about sending more emails. They’re about sending the right email at the right moment in the guest journey. For those unfamiliar with the guest journey, it refers to all the steps a traveler goes through before actually booking a trip.

Before booking: Welcome (new subscriber), Abandoned cart (started checkout but didn’t finish)

After booking: Booking confirmation, Trip extensions (upsell additional nights), Pre-trip preparation, Check-in day

After staying: Post-trip review request, Flash rebook (same dates next year), Stay again (anniversary reminder), Guest winback (re-engage lapsed guests), Convert OTA to direct

Each of these triggers at a specific moment. Each serves a specific purpose.
Let’s break down the ones that have the biggest impact.

The highest-impact automations

Abandoned cart recovery

This is your highest-ROI automation. Someone selected your property, picked their dates, maybe even entered their payment info—then left. These are hot leads.

When it sends: 4 hours after checkout started without completion

What it does: Reminds them exactly what they were looking at and makes it easy to finish.

Example:

Subject: Mountain View Lodge is still available

Hi Sarah,

You were looking at Mountain View Lodge for 3 nights starting March 15, 2024.

Still open:

• March 15, 2024 – March 18, 2024

• 3 nights, 4 guests

• $1,247

[Reserve now →]

Questions? Just reply.

Why it works: No fluff, no hard sell. Just the facts they need to finish what they started. The “Questions? Just reply” line opens a conversation if something was blocking them.

Industry data shows abandoned cart emails recover 10-30% of abandoned bookings. For most property managers, this single automation pays for your entire email platform.

Flash rebook

Catch guests while the experience is still fresh. This goes out 10 hours after checkout—before they’ve even unpacked at home.

When it sends: 10 hours after checkout

What it does: Offers them the same dates next year at this year’s price.

Example:

Subject: Same weekend next year?

Hi Sarah,

You just checked out from Mountain View Lodge.

Want the same weekend next year? Reserve it now at today’s price.

March 15, 2025 – March 18, 2025

2024 pricing locked for 2025

Offer good until Friday, March 22 at 11:00 AM.

[Reserve for 2025 →]

Why it works: You’re asking when they’re happiest—right after a great stay. The price lock creates urgency without being pushy. This automation fills your calendar a full year in advance with guests who already love your property.

Trip extensions

Most property managers leave money on the table here. If someone books Thursday-Sunday but you have Wednesday and Monday open, why not offer them?

When it sends: 2 days after booking confirmation

What it does: Checks for available nights adjacent to their reservation and offers to extend.

Example:

Subject: 2 more nights available at Mountain View Lodge

Hi Sarah,

Mountain View Lodge has 2 nights open after your stay.

Current booking:

March 15, 2024 – March 18, 2024 | 3 nights | $1,247

With extension:

March 15, 2024 – March 20, 2024 | 5 nights | $2,045

Want them? Reply and I’ll add them to your reservation.

Why it works: You’re not asking them to book again—you’re offering to make their existing trip better. The side-by-side comparison makes the decision easy.

Convert OTA to direct

Every Airbnb or VRBO guest is a potential direct booker. You just need to show them why it matters.

When it sends: 48 hours after an OTA checkout

What it does: Thanks them for staying and plants the seed for booking direct next time.

Example:

Subject: You booked Mountain View Lodge through Airbnb

Hi Sarah,

You just stayed at Mountain View Lodge in Asheville, NC. Thanks for that.

When you book direct, you skip the platform fees. That’s usually 15-20% back in your pocket.

Why else:

• You talk to me, not support

• More flexible policies

• Honest pricing

[Book direct next time →]

Why it works: You’re not criticizing their choice—you’re educating them on an alternative they probably didn’t know existed. Over time, this shifts a meaningful percentage of your OTA guests to direct channels.

The foundational automations

These aren’t the flashiest, but they’re essential for a complete guest experience.

Welcome email: Sends 5 minutes after account creation (if they didn’t immediately book). Introduces you and gives them a reason to browse.

Booking confirmation: Sends 5 minutes after booking. Confirms reservation details and sets expectations.

Pre-trip preparation: Sends 3 days before check-in at 9am property time. Check-in instructions, amenity details, location information.

Check-in day: Sends 8am on check-in day. Final confirmation with WiFi details and contact info.

Post-trip review request: Sends 24 hours after checkout. Simple ask: How was it? Leave a review.

The retention automations

Stay again (anniversary): Sends 11 months after their original stay. Reminds them of their trip and checks if the same dates are available next year.

Guest winback: Sends 9+ months after checkout if they haven’t rebooked. Offers a discount code with an expiration date.

What makes these work

Notice what’s consistent across all these emails:

They’re triggered, not batched. Each email sends based on a specific guest action—booking, abandoning cart, checking out. You’re not blasting your whole list with the same message.

They’re personal, not promotional. The tone is one property manager talking to one guest. Questions? Just reply. Want them? Reply and I’ll add them.

They’re useful, not annoying. Pre-trip sends check-in codes. Check-in day sends WiFi passwords. Every email has a clear reason to exist.

They respect timing. Abandoned cart waits 4 hours (not 4 minutes). Pre-trip sends at 9am in the property’s timezone. Flash rebook catches them 10 hours after checkout when they’re still glowing.

Setting this up yourself vs. having it done for you

You can build these automations yourself. Most email platforms—Mailchimp, Klaviyo, ConvertKit—support triggered emails and basic personalization.

But here’s the reality: it takes time. You need to set up each automation with the right trigger, build the templates, connect your booking system, test everything, and monitor deliverability. For most property managers, this is 40-60 hours of work before you send a single email.

That’s why we built it into Wander Sites. When you launch a direct booking site with Wander Sites, these automations come pre-built. Abandoned cart recovery runs automatically. Check-in instructions send themselves. Guest winback campaigns trigger when they should.

You don’t configure anything. You just turn it on.

The same email infrastructure behind $55M+ in bookings—now powering your direct booking site.

Start here

If you’re building this yourself, prioritize in this order:

1. Abandoned cart — Highest immediate ROI

2. Booking confirmation + check-in day — Essential guest experience

3. Post-trip review request — Build social proof

4. Flash rebook — Capture rebookings while intent is high

5. Everything else — Layer in as you have time

If you’d rather skip the setup and start with everything working, Wander Sites includes all of this out of the box.

Your guests want to book direct. Make it easy for them. Get started for free at wander.com/sites