Automated Vacation Rental Gap Night Discount Offers
Every morning, WebRun scans your Guesty calendar for orphan or gap nights between bookings, identifies past guests or inquirers who might fill them, drafts a targeted discount offer in Gmail for your review, and logs every gap and offer in Google Sheets so you can track fill rates.
How can I automatically offer discounts to fill orphan gap nights in my vacation rental calendar?
Every morning, WebRun scans your Guesty calendar for orphan nights between bookings in the next 30 days, identifies past guests or inquirers who might fill them, and drafts a targeted discount offer in Gmail for each gap. You approve what goes out. Every gap and its fill status is tracked in Google Sheets.
- Orphan nights that would have gone empty are proactively targeted with offers
- Past guests see a personalized deal, not a generic discount blast
- A Sheets log tracks which gaps fill and which discount rates convert best
Built for vacation rental managers · short-term rental hosts · property management companies · Airbnb and Vrbo hosts aiming for higher occupancy
What does WebRun do on every run?
The exact actions WebRun takes, in order - in plain language, so you can adjust anything.
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WebRun signs in and gets to work
Opens
app.guesty.comin a real browser with your saved login - no setup, no API keys. -
1
Guesty - find orphan gap nights between bookings
guesty.com
WebRun opens Guesty to find orphan gap nights between bookings. - Open Guesty and scan the calendar for gap nights of 1 to 3 nights between confirmed bookings in the next 30 days
- For each gap, note the property, the gap dates, and the surrounding booking context
- Pull any past guests who stayed at that property or inquirers who asked about overlapping dates
Done when All gap nights in the next 30 days are identified with their properties and potential target guests.
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2
Gmail - draft targeted discount offer for potential guests
gmail.com
WebRun opens Gmail to draft targeted discount offer for potential guests. - Draft a friendly, time-sensitive discount offer for each gap night, addressed to a past guest or inquirer by name
- Include the discounted nightly rate, the available dates, and a direct booking link
- Leave each draft unsent for your review before it reaches the recipient
Done when A ready-to-send gap night discount offer draft exists in Gmail for every identified gap.
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3
Google Sheets - log gap nights, offers sent, and fill status
google.com
WebRun opens Google Sheets to log gap nights, offers sent, and fill status. - Log each gap night with property, dates, discount rate offered, target guest, and draft status
- Mark gaps as filled when a booking comes in to track your conversion rate
Done when All gap nights and their offer drafts are logged in Google Sheets with fill tracking.
How is each run configured?
Secure by default
Connect once, stays signed in
WebRun signs in once and keeps each session in a persistent environment, so every run picks up right where it left off.
Every action is checked against this policy before it runs.
Questions, answered
Will it send discount offers to guests without my approval?
No. Every discount offer is drafted in Gmail and left unsent. You decide which ones to send so you stay in control of your pricing and who receives offers.
How does it find guests to target for a specific gap night?
It looks for past guests who stayed at the same property and inquirers from Guesty who asked about dates close to the gap. You can also specify a target guest list during setup.
What if a gap night gets booked before I send the offer?
WebRun checks the live calendar each morning, so the next day's run will not draft offers for gaps that have already been filled.
Related templates
Put this on autopilot.
Turn it on in minutes - or have our team set it up for you.