5 Secrets to a Successful Airbnb

Jenna Kutcher 

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September 29, 2017



He laughed at me when I casually said, “Wow, I didn’t buy much in Hawaii, just that one cute sweatshirt.” He looked me in the eyes like I was a fool and said, “Um, we also happened to purchase a condo that cost more than our entire home in Wisconsin.” Ohhh… yeah, that thing. When we planned our month getaway to Hawaii it was purely a trip to rest that turned into so much more. We were flying home with offers sitting on the table to purchase our own slice of the island that we had grown to love and we were first time property investors at the ripe age of 28…

I quickly found myself googling: “How to have an awesome Airbnb?” or “what makes a successful vacation rental?” and while some articles gave great tips, I didn’t feel like I felt fully prepared for what owning our own property was going to look like for us, especially being a short 10 hour flight distance away! We got home and got planning out our space. What furniture would we get? What would make it feel like home? How would we get things to the island? How could we create an experience that shared our favorite place with guests? I’m sharing the 5 biggest secrets we learned in the last six months of owning The Kutcher Condo!

1.) Go Beyond the Basics:

We’ve stayed at many Airbnb‘s in the last few years and most of them just have the basics, but we wanted to do more than that. We asked ourselves what things we wish we had when we were here on the island, ya know, the stuff you can’t easily fit in your suitcase! We stocked up our place with alllll the beach needs including: an umbrella, two fold out chairs, a cooler, beach towels, beach mats, sand toys, a beach bag, snorkels, we even have sunscreen and aloe! This helps our guests save money on their vacation AND allows us to share some extras that will make their stay easy and enjoyable.

Another thing I was serious on was not skimping on cheap linens or bedding! There is nothing worse than getting to a place and finding an uncomfortable bed or terrible pillows. While on the island I stumbled into Cariloha an incredible island shop that sells bamboo sheets, towels, and robes and I KNEW we had to have them in the condo. We have two plush robes for our guests, awesomely soft towels, and sheets that make you want to stay in bed!

2.) Communicate Clearly:

Communication is HUGE! You want your guests to feel valued, understood, and to equip them to have the best time ever. We sat down and created message templates that help communicate how to enter the building, where to park, check in and check out policies, and we make sure to get their flight info so we know when they arrive on the island and get to the unit. It’s also awesome to just check in with your guests and see if they need any recommendations or ideas while visiting. We created a beautiful guestbook for our condo so our guests can see our island pictures and feel like they can know us while leaving a little message about their stay! On top of that, we have a little “quick facts” sheet and booklet out upon arrival so all of the important information is laminated for our guests and easily available should they need any help!

We understand that checking into a new place can be confusing or complicated and so we wanted to make it as easy as possible. Not only do we email all of the information to our guests but we also decided to streamline the process and installed a Schlage lock on our door so that our guests can use a simple key code to access our place without fumbling around with a lockbox or dealing with keys that can be easily lost in the sand. It also allows us to give our cleaner and manager personal codes and see on our app who is entering the building and when. The most amazing thing is that you can access all the info from an app on your phone, so you can see that the place is secure, who’s entering, and you can even unlock it from your phone. This added ease and security Schlage offers is worth every penny!

3.) Create an Experience Online:

When you browse Airbnb, there are a ton of places that all blend together because they start to look the same! When we were brainstorming our design for the space we wanted something super clean and minimal while still feeling like home. We blew up our own personal drone photos and hung them on the walls for art, we leave a signed print for each guest who visits us and leave a bottle of wine out for them to enjoy! I also took the time to style images of our place in a unique way so that it felt lived in and enjoyed, instead of just feeling like a little home tour. We also shot a drone photo of the beach by our place to capture the attention when people are scrolling the app and took images that set the stage and tell a story beyond just a building.

Incorporating items like: branded pillows, branded coffee mugs, heck, we even put our logo on a surfboard (I know, I know, I made our condo a logo!) I also knew I wanted to put together a place to share about our Hawaii home and our favorite beach spots, adventures, and restaurants on the island so we created a website and an Instagram account for the condo so that people can fall in love with our space beyond the platform it’s hosted on!

4.) Have an Awesome Team:

One of the scariest parts of getting our place was figuring out who would manage it and what that would look like for us living so far away! For many places on the island, the building that you’re in can manage our place for you and take a percentage of your profits but then you’re pretty hands off. We wanted to be more hands on with our place to host people that felt more like friends and family, even if they were mere strangers and so we decided to hire an on-island rep (required by the state) to help manage our cleaning and maintenance while we handled the bookings. Our rep, Dave with Rentals Maui, works with our booking calendar and schedules the cleanings and then does walk-throughs and inspections of our place before each new guest arrives! Not only were we able to screen our own guests but we were also not giving up a percentage of our income because we were taking on that piece of things!

We interviewed a few cleaners on the island based off of our managers recommendation and found an amazing husband and wife team who treat our place like their own and make sure it’s perfect for each incoming guest. We also found an awesome father-son duo, Rob and Justin with Aliikui, who does INCREDIBLE maintenance work and they show up on time, every time and have been some of the greatest people to work with. Being on an island, recommendations can make all the difference so if you can have any connections, pay attention because all of this happened because of our realtor who connected us to our manager who connected us to our cleaners and maintenance team!

5.) Have fun with it:

We wanted our place to be fun and feel like home so we included items like: a Bose bluetooth speaker, a few board games, a bar cart, a Roku so people could access their Netflix and fave TV shows, and more. We wanted to under promise, over deliver for our guests while being reasonable that most days people would be at the beach enjoying the island! I still can’t believe we own a place on Maui! It’s pretty incredible and it’s such a gift. We want to enjoy our time here just as much as our guests do, so we block off time for us to come to the island, make improvements on the condo and rest and relax. We are always looking at how we can make our place better for our guests and what WE would want from a place.

Owning a rental property can be a lot of work but just like all things in business, if you can systemize and create templates, it’s not as hard as it might feel to run a successful Airbnb. We were shocked when we got back after five months away how our place looked and felt just as we left it (even though over 20 guests had enjoyed it!) Since we have such a great team supporting us and incredible guests who respect that we own, pay for, and care about our space, we’ve had such an incredible experience hosting and sharing our slice of the island with others and it’s simply a joy to be able to open our doors and welcome people in!

Website: The Kutcher Condo // Airbnb listing: Click here 

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  1. Julie says:

    We have lake property with our main lake house and a cottage on it. We have been thinking of listing the cottage on Airbnb and this is just stronger motivation ! We also just put an offer in on the land next to us with the thought of building a tiny or tree house on it. We always use Airbnb/VRBO when we travel so its crazy that we have not yet taken the leap with our cottage. We live in Augusta GA where the Masters comes to town and everyone rents their house and we have yet to do that either ! I am feeling motivated after reading this post !! Your guest book is gorgeous. I am curious about he pages where they can leave comments … are there sections for that or are they free to leave them wherever in the book. It looks like it may come from Artifact Uprising or somewhere similar. We visited Maui this summer and when I return I will be staying at Kutcher Condo for sure !!

  2. Christie Brophy says:

    Thanks for all the info! In escrow right now on a vacation rental in Maui! Haven’t even stepped foot inside it yet, but can’t wait to get over there to personalize it. Where did you get the custom surfboard from? Also any recommendations on a good handyman or painters?

    • Congrats Christie, that’s so exciting! We found the surfboard on Etsy and then we used Top Gun for painting. You generally have to go through your HOA for any updates and/or contractors so ask them who they refer that knows the complex well! Enjoy!


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A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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