Often times, I travel last minute so am fairly used to concocting solutions at the 11th hour. On a recent trip to the Bay Area, though, I experienced an epic last-minute travel fail with my two usual stalwarts: HotelTonight and AirBnB. I will explain how you can prevent a similar mishap so you can avoid AirBnB and HotelTonight fails and not end up homeless while traveling.

First, a word about the two prominent services available for the travel warrior. HotelTonight is an app that offers discounted hotel rooms, for the day of travel, based on filling last minute room inventory. The savings are deep, even at the most swanky hotels. AirBnB turns any property owner into a renter, giving them an opportunity to rent their house or room to strangers throughout the world, including Cuba.

Now, on to the situation that left me sleeping on this:

air mattress on the floor

AirBnB had an air mattress on the floor

Hotels were scarce in Silicon Valley on this particular week in early May due to the Apps World Conference, which I planned to attend to promote my app project ChumMe. Searching in advance, hotels were either incredibly expensive or very far from the conference so I thought I would leave fate to chance, knowing that HotelTonight had never left me without a roof before.

So I booked the flight about a week in advance and was confident I would find a place on HotelTonight, especially since my stay would only require one night. It turns out that a twist of fate was on the horizon. On the day of travel, I opened my HotelTonight app to no avail. No properties found. Nada. Zero.

“Okay, don’t panic,” I said. There is always AirBnB, right? I had only used AirBnB once in Denver and had a quite pleasant stay. The only property available on AirBnB was a shared room for $99 in Sunnyvale, CA – a short 20 minute drive to the Santa Clara Convention Center, where Apps World was to be held. What could go wrong, right?

AirBnB Fails: The Arrival


I arrived after 9pm to this dark alley – no lights, no sounds. My Uber driver, probably feeling my nerves, asked me if I wanted him to wait to make sure I was in the right location.

I wasn’t sure if it was the correct spot as there was no illumination indicating a street address. I sent my driver on his way, wondering all the while if I would ever see my kids again.

The door leading to the AirBnB shared room in Sunnyvale, CA

The door leading to the AirBnB shared room in Sunnyvale, CA


Guessing the right doorway, it led me upstairs and I knocked on the door at least three times – louder with each knuckle tap. Finally, a bearded 30-something opened the door. He looked like he had just finished a 24-hour stint playing Dungeons and Dragons.

Walking in, a white drape greeted me that separated the living room from the kitchen. The curtain was sheer enough to see through it and see stuff – everywhere! The place could have easily been a candidate for Hoarders.

The gentleman, kind yet awkward, led me to my room for the night.

The Waldorf-Astoria it was not.

The room was what we will call “minimal.” The mattress was full of hot air…literally! It was an air mattress on the floor. The desk was adjacent and that was it. The door didn’t lock to boot!

airbnb fails

AirBnB Fails include an air mattress that sits on the floor of a very weird apartment

He and a girl (I could tell from the voices coming through the door) were easily heard from my non-penthouse room most of the night. They weren’t loud enough to warrant a formal complaint but I did hear them up and about most of the night, which kept me from falling into a deep slumber in my little air bubble on the floor in the middle of Sunnyvale. I actually published my location to my Facebook feed in case I went missing in the night.

To sum up…

Tips to Avoid Last Minute Travel Fails

  • Plan ahead! Make sure you have backup options in case you can’t find anything on HotelTonight.
  • HotelTonight offers reservations in advance (just a few days’ advance) now  so check daily to see if something comfortable is available.
  • Read reviews on AirBnB about the lodgings to get an idea what’s in store for you.
  • Get the cell phone number of your potential AirBnB host and communicate before the day of travel to make sure you’re comfortable with the person.
  • Let someone know where you are and give them a time that you will check-in the next day.