12 Things I Learned After 90 Days on Airbnb

At the end of 2021, I signed a bunch of papers and closed on The Flying Squirrel—a mountain cabin in Maggie Valley, NC. Shortly thereafter, I listed in on Airbnb. In this post I’ll share my learnings from the first ~90 days of business as a remote short-term rental host.

Get. Great. Photos.

When you list, photos are super important. Here’s an example of an early photograph I put on Airbnb:

Living room of The Flying Squirrel

At first glance, it might seem fine. And sure, it got me a couple of bookings. But after chatting with David over at Overlooked2Overbooked and using their Vacation Rental Assessment (highly recommend), I learned several things:

  1. My photos were not bright enough
  2. My photos did not show enough primary colors
  3. My photos didn’t tell a story

So here’s some of my newer photos.

A bit better, yeah?

You don’t need a management company

Management companies like Vacasa will run your vacation rental for you and take a cut of the proceeds. Here’s why I don’t recommend starting with a management company:

  • Once you set up some basic automation, the daily/weekly workload is actually quite low. I can spend as little as ~1-2 hours/week.
  • Running a short-term rental is fun! I have the chance to introduce people to one of my favorite areas in the world.
  • You can (probably) make more money on your own. Not only will a management company take a sizable cut from your payouts, they also won’t have the expertise on your property or even your market that you do. There are a lot of high quality free resources to help you improve your short-term rental game. Like this blog. 👀

Pick an area you know

When I decided to start a short-term vacation rental company, I knew ahead of time that I’d be looking in the Great Smoky Mountains area. Despite living in Texas my entire life, I do have some familiarity with the area from a month-long stay in Asheville in 2021 (via Airbnb, of course).

This gives me some advantages:

  • Recommendations are much easier since I’ve spent time there as a guest
  • I knew which areas to target. When I stayed in Asheville, I found myself driving through this little town called Maggie Valley to get to the best trailheads.
  • More visits! I find myself visiting the North Carolina area quite often, so having a place to stay there is a nice bonus.

I got lucky in that the area I know well is great for short-term rentals. If you have a market in mind that you don’t know well, that’s fine too. Just make sure to follow my next tip:

Find an excellent local partner

This applies to anyone doing remote hosting.

I recommend finding the person who will be cleaning your property fairly early. This person can make or break the guest experience. I got very lucky because the first person I reached out to ended up being excellent.

While there are platforms like TurnoverBnB that will help you find and facilitate cleanings, for a single-property manager, this is overkill and expensive.

I found my cleaner by poking around on Facebook. I literally just searched “housekeeper maggie valley” and contacted the first person I found. It turns out that the person I found runs a short-term cleaning company. I see this as a major perk, because:

  • She has experience with short-term rentals
  • She has backup cleaners on her team
  • Our incentives are aligned—if guests have a good, clean experience, that means higher occupancy in the future, which means more cleanings

Another major perk: My housekeeper is good at doing small repairs! When my brand new bed broke, my housekeeper fixed it right up, meaning I didn’t have to wait for someone else to take a look. Find you somebody that can do both.

Live in your property

If at all possible, live in your property as you get it set up. Because I work remotely, I was able to work from there as well. Having to cook, clean, recreate, be bored, etc in your property will help you get those “must-have” items you forgot to grab. You’ll have more ideas on how you can create an awesome experience. Your recommendations will be stronger as you find the best local spots. Plus, it’s fun.

You only need one tool (pricing)

If you listen or read in the STR space, you’ll no doubt hear about the various tools available to use. As a software nerd, I was tempted to pick out a few that sounded interesting and get them set up immediately.

What I recommend instead is to wait. Don’t purchase a tool until you feel the pain of not having it.

As a quick example, I thought I needed a platform to help with automated messaging. Since I only launched on Airbnb, I was able to use Airbnb’s built-in free tool. It does everything I need it to do.

The only tool I think you should start out with is a pricing tool. Pricing is crucial to your listing’s performance and requires a lot of effort to get right. I use Pricelabs, which provides some nice features:

  • Automatic seasonality and occupancy based pricing
  • Ability to set orphan day discounts (if there’s a space in between two other bookings, discount it)
  • Last-minute discounts are helpful for increasing occupancy rate
  • And more!

For about $20/month, this is a no-brainer.

If you’d like a screencast walking through Pricelabs, please reach out to me on Twitter!

Note: Airbnb does have a built-in dynamic pricing tool. However, I’m wary of it since their incentives don’t align perfectly with mine. Anecdotally, I’ve heard that they tend to focus on optimizing for occupancy rate, not overall revenue.

Why I launched on Airbnb only

Up until yesterday, I was only on Airbnb.

Being on one platform simplifies almost everything. With this being my first vacation rental, simplicity is key! It also helped me reach Superhost status before the April 1 deadline.

That being said, use something like AirDna to figure out which platforms your market uses. Here’s the breakdown for Maggie Valley:

Where my competition lives

I picked Airbnb over Vrbo because I prefer Airbnb for my own stays and knew the platform already.

Be available

I’m normally a heavy “Do not disturb” user on my phone. However, with owning a short-term rental, I’ve had to make some adjustments. You want to be able to respond to inquiries and guest problems as quickly as possible. It means more bookings and better reviews. I’ve already had multiple instances where had I not been available, a guest would have been locked out for hours.

The way I stay available is by bypassing my “Do not disturb” setting on my iPhone if the notification is coming from the Airbnb app.

Only Airbnb and a timer app can get through DND

The best reviews start before the guest visits

Looking at the best and kindest reviews I’ve received, they mostly come from guests that I’ve communicated with ahead of time.

I like to reach out a few days before my guests stay and ask if they have any questions or would like any recommendations. I do sometimes forget, which is why soon I’ll set this up as an automated message.

But by getting a conversation going with a guest, I get a chance to establish myself as a real person. One of my competitive advantages is that I’m a real person and not a faceless management company! Guests who know who you are will be more likely to, for example, crawl through a window to unlock a door that got locked from the inside (yes this happened).

Have backups for crucial items

Sometimes, you get a message from a guest saying the key broke off in the lock. 😬 If you have two lockboxes and a spare key, this is not a problem! I’d also recommend having backups for:

  • All bedding
  • Towels
  • Heating/cooling

I 💖 consignment stores

You know what’s expensive? Furniture. Luckily, my area has these things called consignment stores and they’re amazing. Here’s the quick pitch: stuff, but used and cheap. Depending on your market, you might not be able to find what you need. But since I was building a mid-market mountain cabin, the consignment stores in my area were a perfect way to save some cash and find unique items.

Don’t worry about low rates (at first)

My first few nightly rates were abysmally low. As low as $60/night for a 3/1 in the mountains. However, these prices got guests in the door, which led to reviews and learnings. Since then, I’ve been able to charge as much as $179/night.

In the beginning, don’t worry about how much money you’re making. Just find a rate that will get guests to purchase, then focus on making an excellent guest experience and continuously tweaking and improving your listing.

In other words, optimize for occupancy, not revenue in the early days. Get those reviews, improve your listing, and soon you’ll be able to charge much more.


I hope something in this guide was valuable, dear reader. I’m still very new to this game and will continue to learn. To follow along, please consider subscribing to my newsletter.

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