After investing in 4 rental cabins in 4 years, earning nearly 500 5-star reviews, approaching a 7 figure revenue and Airbnb Superhost status—we’re sharing what you need to know to run a wildly successful vacation rental biz (and book out up to a year in advance).

This has been the key to our success, and I want it for you too, friend.

Here’s one of the biggest lessons I have learned in my decade-long career coaching small businesses and entrepreneurs: you need to build your business in places you have control over.

Do you have any control over Airbnb? No. They could decide tomorrow they are done and closing their doors and your entire business could be in jeopardy. I sincerely don’t want this to happen to you and so, here are our 10 best tips for growing your short term rental business in a way that puts you in the driver's seat of its future.

Number One:

Owner Rez

Your first step in executing a strategy in a place you can control is to have a place where you can accept bookings on your own. We’ve done the research and the best company to partner with to accomplish this is Owner Rez. Their customer support is next level and you’ll have everything you need for the back end system of accepting and managing your bookings on your own. We also love that it easily integrates with other booking platforms like Airbnb and VRBO so you only have to make updates in one place and have them executed everywhere you accept bookings.

You can join right here

Number Two:

Showit or Squarespace

Once you have the technology to accept bookings, you need a place to host it! My favorite website hosting companies are Showit (what we use) and Squarespace. Both of these offer beautiful pre-made templates so all you have to do is update them with your photography, branding colors and copy and you can be up and running pretty quickly. Or, if editing a website template feels too difficult, there are graphic designers you can outsource this to as well. Our favorite: Madie Lerue.

Number Three:

Flodesk

Next, let’s make sure to capture anyone who visits your property or your site so you have a way to get in touch with them in the future. Why is this important? We want to stay front of mind so that when someone is ready to book a vacation rental, we are who they think of. It’s also a great way to keep interested future guests in the know of any updates we have like when we open the calendar for the following year or if there’s a last minute cancellation and any promotions. To implement this strategy, you’ll need an email marketing service provider and our favorite because of it’s beautiful designs and intuitive set up is hands down Flodesk.

get 50% off flodesk here

Number Four:

Content
Strategy

Now that we have a way to capture people onto an email list, how are we going to keep them there and engaged so that when they have a vacation need YOU are who they think of? The answer is your content strategy and this means we are going to create emails or blog posts that serve our audience with insider information about visiting your area. Does this make you worried about how much work this is going to take? Let me simplify it for you. I want you to write ONE post or email a month that helps a future guest plan their trip.

These posts can be as simple as things like;
- “10 best restaurants in <insert your area>”
- “10 Most Instagrammable Spots in <insert your area>
- “Our Families Favorite Things to do in <insert your area>.

You can write this content in your sleep, and it’s going to showcase you as the expert in your area and be a resource to your guests and future visitors.

Number Five:

Creating an Experience

Now that we can showcase what it would feel like vacationing at our property visually, let’s make sure to infuse other touch points into our guests' experiences that show we care about them and their vacation. It’s this step that I feel like makes the biggest impact and leaves us with friends after a guests vacations (and keeps them coming back year after year). Brainstorm ideas that you can infuse communications to let our guests know we care and are there to support them.

This can look like a helpful pre vacation email with a welcome guide, a night before check out reminder of check out procedures so they have them at their finger tips, a gift upon check in, a Christmas or birthday card each year - this little easy steps make a huge impact when creating an experience for our guests that get them talking about staying with us and helping spread the word about our vacation rentals.

Number Six:

YOU, yes YOU

Yes, you read that right, YOU are a key piece to a book direct strategy. I want you to tell your story, share why you love your location, let your guests into your life and personalize the experience for them. Why? Because otherwise you are just like any hotel down the street. People need to know, like and trust you before they will hand over their money and invest in a vacation with you. This key marketing principle is especially important in this industry because your customers are staying in your home and it’s such a personal experience.

The way we do this in our business is to make sure our face shows up on our social media posts, we tell our story on our about page, we personally connect with our guests via text or email before, during and after their stay and they leave the vacation feeling like new friends.

Don’t hold back, people want to know you, the story behind your property and so make sure to show up and connect with them.

Number Seven:

Support local small businesses

I love small businesses and so it was a natural step to support them with our vacation rental whether that was in the decor we purchased for our home or the local coffee we had on hand for guests. This turned out to be smart for our book direct strategy as well because we’ve gotten referrals from the landscape photographer we purchased artwork from, the brewery owner and family photographer. Supporting these businesses gave our rental a local personality and supported these businesses we love, and it paid off.

Number Eight:

Photography

If your listing currently consists of iPhone photography and has no people in it, we need to talk for a second here. Investing in your photography is so important because it’s often the deciding factor for our future guests when picking one vacation rental over another. They need to be able to envision themselves vacationing there and to do that, we need people in our images and styled photos of our spaces being used in a beautiful way.

1. Invest in a photographer. This investment will pay dividends for years to come so don’t stress about the financial piece of this. My advice is to find a great lifestyle photographer who’s style fits with the vibe of your property. My favorite: Colleen Wolbert Photography because she’s amazing at lifestyle imagery, specializes in real estate styled photos and can offer a 3D Tour of your space as well (check ours out here!).

Your second option is to 2. Look for local influencers who have photography skills as well. This is going to be a double win because often we can trade a stay at our property for not only exposure to their audience when they share, but also gain images from their stay to use to promote our properties in the future.

If your photography skills don’t measure up, you have a few great options.

Number Nine:

Convert your Airbnb Bookings to Book Direct

Don’t misunderstand me when I say a book direct strategy is the key to our success to mean that we don’t also lean on Airbnb as a key part of our strategy. This site is going to be your main source of new bookings in the beginning and we want to use this site to the best of our ability while it’s still an option while also preparing for being independently responsible for finding our own bookings. Still focus on this piece of your business plan while also being mindful of how we can convert our Airbnb guests to a book direct strategy the following the year.

We do this two ways: we make sure to add their email to our email list so they get future communications from us directly and we stay front of mind. We also let them know we hope they’ll stay with us again next year and that they can save booking fees if they book direct. Educating guests that they have this option is one of our goals in a book direct strategy especially now that they know and trust us.

Number Ten:

Cultivate a place where your can continue to find leads on your own

Airbnb will be a great source of bookings for you, but we also want to start to build another way to find and attract new guests. The best way to do this is to be active on a social media platform. You read the singular “a” right - I don’t want to overwhelm you and make you feel like you have to have a presence in all the places. I know from my years of working with small businesses, that this is a recipe for failure because it becomes overwhelming.

I’d much rather you pick one platform you love and be consistent there because showing up regularly is the key to success on any social media platform. For us, it’s Instagram because it’s such a visual site and we can showcase our properties and connect with our guests and people interested in our location by targeting hashtags. 

there you have it!

Mastering these 10 steps will ensure you are setting your vacation rental business up for success not only now, but well into the future.

Each year, it’s easier and easier to fill our calendar with guests just waiting for the email that says our calendar is open and then we will fill the straggler dates with Airbnb bookings. 

I’d love to know where you’re at with your business, which steps you love and which ones feel like you need additional support with! Feel free to reach out, talking vacation rental business is one of our absolute favorite things!

Jeremy & Caitlyn