6 Things I Wish I Knew About Short-Term Rentals Before I Started

I started my short-term rental (STR) business (on Vrbo and Airbnb) with 2 cottages in my back yard and a camper (with utilities) in my driveway in January 2021. Now, I have a total of 8 short-term rentals that I own and manage myself. I’ve learned a lot along the way, but here are the 6 things I really wish I knew before I started:


1. STRs are a cross between real estate investing and hospitality

When I set out on this journey, my goal was to expand my real estate portfolio, to become a true real estate investor. I was looking for cash flow and appreciation. Naturally, short-term

rentals offer more cash flow. It was a good financial move, but I didn’t think enough about delighting guests. Hospitality became my part-time job.


2. Managing STRs means always being on call

Even with cleaners making their own schedules, automated emails, and locks that set themselves, communications can occur at pretty much any time. A cleaner may reach out with a supply need. A potential guest may be wondering how long a drive it is to the airport. Whatever it is, from the time I wake up until the time I go to bed, I’m on call. Luckily, it’s only a few messages a day that don’t take much time.


3. People don’t read

Do my listings say how far it is to the airport? Yes. Do I still get that question? Yes. It seems most guests look at pictures and skim listings. Be prepared to answer questions your listings and communications should be able to answer.


4. Tweaking communications is a regular thing

Don’t give up tweaking though. Just because guests are less likely to read, it doesn’t mean all of them won’t. When I get a question 2-3 times, I start looking for how to make that portion of the listing or email stand out. I’m making tweaks at least weekly.


5. You must be proactive

I’ve been at this long enough that sometimes I start feeling like something is off with a guest or the cleaner. If you have a hunch something is up, check the locks or the cameras or the messaging. Get ahead of problems.

6. You will f*ck up

There is no way to get it all right all the time. Cut yourself some slack. Fix problems as they arise. And set yourself a “f*ck up budget.” We all have one.


Just because there are some things I wish I knew before I started, that does not mean that I wouldn’t do it all over again. There are many rewards to STRs, financial and otherwise, and I recommend giving it a try. Don’t be afraid to jump in and learn along the way like I did.

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