We all know that running a successful short-term rental business comes with its own set of challenges. This is especially true when learning to manage multiple properties, cleaning schedules, and pricing strategies. We’re here to remind you how Host Tools simplifies property management and helps hosts earn as much as possible by keeping their booking calendar full. Below, we’ll explore specific features, including two powerful message rules, that help short-term rental hosts fill their calendars and increase profits.
Host Tools provides an automated, unified calendar for short-term rental hosts, allowing you to seamlessly list on all major channels. Start your free trial today!
Encouraging repeat bookings with post-stay marketing messages
One important element of building a sustainable business is fostering a strong relationship with guests. This type of relationship-building encourages them to think of your property next time they’re in town. Host Tools enables users to set up automated marketing messages targeted at previous guests, inviting them to book another stay. This feature sends personalized messages to past guests nine months after their stay, presenting them with the perfect opportunity to plan another visit.

How to set up the rule
To create a post-stay marketing rule on Host Tools, first head to the Message section on your dashboard. From there:
- Select the option to create a message rule.
- Specify the timing for the message—set it as nine months after a guest’s previous departure. This is about 270 days.
- Personalize the message to make it engaging. For example:
- Use a tag to greet the guest by name
- Offer a discount or special promotion for returning guests.
- Include a clear call to action, such as a direct link to book their next stay.
- Target these messages to all previous guests, or tailor messages to specific groups based on how many nights they stayed.
Learn more about how to send marketing messages via our help article.
Why it works
This strategy works well with guests who have stayed at your property because they already know that you’re a great host. Sending this message nine months after their stay is the sweet spot, as it gives guests enough time to have moved on from their trip, but still recently enough for them to look back fondly on their stay and smile. A great way to spice up this strategy is to offer discounts.
How to fill gaps with extra nights offers
Another way to fill your calendar is by offering guests additional nights before or after their existing reservation. Host Tools makes this easy with automated messages designed to encourage guests to extend their stays. This feature is particularly useful for filling otherwise vacant nights between bookings.

How to set up the rule
This automation can also be set up within the Messages section of your Host Tools account:
- Create a message rule tailored to offering extra nights to current guests.
- Set the timing for the message. A great time to send this message is a few days before the guest’s scheduled check-in or check-out.
- Customize the message to align with your pricing and availability. For example:
- Clearly mention the discounted price or special deal for additional nights.
- Highlight the convenience of extending their stay without having to move to another property or re-book elsewhere.
- Add a sense of urgency, like mentioning limited availability or a deadline for accepting the offer.
- Automate the rule so it is only sent to guests who have reservations with room for extension on either side of their booking.
Read more about how to set up this messaging rule in our help guide here.
Why it works
Offering extra nights caters to travelers who want flexibility in their plans. Some might find your property so cozy that extending their stay becomes an attractive option, especially if faced with unexpected schedule changes like flight delays.
Additionally, discounted rates or package deals provide value for the guest while ensuring you secure income for nights that might otherwise remain unbooked. With Host Tools automation, there’s no need to manually track available gaps in the calendar; the system does the hard work for you!
The power of automation
Host Tool’s superpower is automation. By taking advantage of advanced features like customizable message rules, hosts can focus on their guests rather than mundane administrative tasks. Both strategies, targeting former guests and offering additional nights, reduce the time and effort hosts need to invest. In addition to these great features, Host Tools offers additional items for your tool belt, like a branded direct booking website, AI auto-replies, automated reviews, and unified inboxes. When combined, these features can save you up to 80% more time. No more wasting time on menial day-to-day tasks.
Automation also ensures consistency. Short-term rental hosts often juggle multiple properties, channels, and responsibilities. Forgetting to send timely emails or respond to guests promptly can lead to missed opportunities. With Host Tools, every guest interaction can be pre-planned, so no potential booking slips through the cracks.

Final thoughts
Host Tools is more than just a property management tool. It’s a powerful ally in the competitive world of short-term rentals. When you leverage our automation tools to send messages to guests who have already checked out, or encourage current guests to extend their stay, you fill your calendars more often than not. This strategy helps you to keep your bookings busy and your pockets full.
Host Tools provides an automated, unified calendar for short-term rental hosts, allowing you to seamlessly list on all major channels. Start your free trial today!
