5 Automations Every Vacation Rental Brand Should Have

If your team is constantly answering the same questions, chasing down check-in details, or missing easy opportunities to rebook past guests, there’s a good chance your automations aren’t doing enough of the heavy lifting. The most effective vacation rental brands use a mix of email before and after a stay, paired with SMS or in-app messaging while guests are in-house, to keep communication timely without overwhelming anyone. When those pieces are in place and used strategically, it naturally leads to better reviews and more repeat bookings. We’ve found that these are the automations that make the biggest impact!

Jump to:

• Welcome emails
• Pre-arrival emails
• In-stay touchpoint
• Post-stay review
• Re-engagement sequence
• Automation with B2 Collab

Email 1: The Welcome Series

The first touchpoint should start the moment a potential guest signs up for email on your vacation rental website. Craft a short welcome series to introduce your brand and give them a feel for what it’s like to stay with you before they’ve even selected a property. Focus on what sets your experience apart, naturally highlighting popular homes, local favorites, and available add-ons. Done well, this early connection builds familiarity and trust, making it much more likely they’ll book when the time is right!

Email 2: The Pre-Arrival Experience Builder Email

This touchpoint should answer the most common questions you hear from guests and be sent before a scheduled arrival. It should also get them excited for their trip and set the tone for a smooth arrival. Be sure to cover the essentials, including check-in details, what to expect at the property, and a few helpful notes. It’s also a great place to highlight upgraded experiences, whether that’s early check-in, tee times, pool heating, or concierge services, while guests are still in planning mode. We’ve found that this email ensures guests show up informed, prepared, and looking forward to their stay!

Email 3: The In-Stay Touchpoint Text

This touchpoint, sent after check-in, is less about marketing and more about being present at the right moment with helpful information. Guests are on vacation, so timing and format matter just as much as the message itself, which is why SMS or an app, like BeHome247, works well. Use this text to cheerfully welcome your guests to their new home away from home. This is a great opportunity to share a few timely recommendations and confirm everything is as expected in their vacation rental, so you can resolve any issues. We’ve noticed that a simple, well-timed check-in text makes guests feel genuinely cared for while adding value in a way that feels helpful rather than disruptive.

Email 4: The Post-Stay Review and Return Invitation Email

This is where many vacation rental brands miss an easy opportunity to turn a great stay into future revenue. This email should thank the guest for choosing your vacation rental company and be sent after checkout. Most importantly, it should also include a direct link to leave a stellar review! Invite them back and introduce referral programs or repeat-guest incentives, if available, and include a small offer to book direct next time. This small gesture helps guide repeat guests away from OTAs and back to your vacation rental company. It’s an ideal touchpoint to automate, ensuring every guest receives a consistent, well-timed follow-up without adding extra work to your team.

Email 5: The Long-Term Re-Engagement Email Sequence

Scheduling follow-up emails 90 days and six months after a stay is a great time to start maintaining the connection. By then, your guests might be ready to consider planning another getaway. They’ll also be much more receptive to any upcoming events or offers you might want to share. Tailor messages to different segments, like families, groups, or snowbirds, to increase relevance and response. You could also include fun itineraries for their next visit to help spark inspiration and bring your destination back to mind.

Vacation Rental Automation with B2Collaborative

Of course, partnering with B2 Collaborative can help streamline every aspect of your vacation rental marketing. Along with driving direct bookings and accelerating owner acquisition, our team can help you build automated guest communications that build long-term loyalty. By leveraging our expertise in segmentation, email automation, and seasonal campaigns, we help you maximize repeat stays while freeing your team to focus on growth! Let’s connect!