October 7, 2024 | 2 Minute Read
Managing a single short-term rental is relatively easy, but handling 13 properties across platforms like Airbnb, VRBO, Booking.com, and Booklee requires processes, systems, and automation.

Tools like calendar syncing, dynamic pricing, instant messaging, WIFI locks, and Google Nest Thermostats are supposed to make management smoother—and they usually do. However, there are times where no matter how much tech we rely on, the process still falls apart.
Last week was one of those weeks. It started with a quiet Tuesday, but quickly went downhill. Here’s the rundown:
Sunday
Even with cameras installed, we can’t catch everything. Early Sunday morning, a neighbor snuck behind The Springfield house, vandalized, and stole the HVAC fan. The entire unit will need replacing at a cost of $5,000. Since we had guests arriving later in the week, we moved them to The Meadows.
Tuesday
A lightning strike caused a power surge at The Birchwood, damaging the electrical system and knocking out the power. With guests set to check in later in the week, we had to move them to The Springhill. Since it didn’t have air conditioning, we scrambled to install five window units just in time for the guests’ arrival.
Wednesday
A guest who had tried to cancel last minute (and demanded a refund) decided to keep his reservation at The Redmont for a one-night stay. Problem solved, or so I thought.
Thursday
The guest at The Redmont overstayed past the 10 a.m. checkout time. After calling and texting him without a response, I had to go to the property myself. I packed up all his belongings and stored them in my Jeep, then cleaned the place with the help of one of our housekeepers before the next guest arrived at 4 p.m. I changed the door code and reported the incident to Airbnb. After contacting the guest, it turns out he thought he’d booked two nights. I met the disgruntled guest to return his belongings and demanded he pay the $150 late checkout fee. Airbnb tried to negotiate, but I held firm, and they charged him the penalty.
Friday
Finally, some good news. the power company restored electricity at The Birchwood. The bad news? Several GFI outlets were fried, meaning no WiFi or power for the washer and dryer. These repairs will have to wait until Monday. But wait! There’s more. Somehow, The Reed got double-booked on Booking.com, with two separate guests arriving at the same property. Double bookings typically happen due to calendar syncing issues between platforms, but this occurred on a single platform. We accommodated one party at The Reed and offered the other The Birchwood, letting them know there was no WiFi or laundry. Thankfully, they accepted.
Summary:
- Guest 1, initially booked for The Springfield, was moved to The Meadows.
- Guest 2, booked for The Birchwood, was relocated to The Springhill.
- Guest 4 was finally checked out from The Redmont, and the next guest arrived on time without issue.
- Guest 5 arrived at The Reed.
- Guest 6, double-booked at The Reed, was moved to The Birchwood.
Got all that? Whew! Despite all the technology in place to streamline the process, none of it worked when we needed it most. Ultimately, it took human intervention to fix everything. Looks like we’re not quite ready for Skynet just yet.