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Proper Insurance

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Five years ago, I gave my current insurance provider (a large and popular residential insurance provider) a call to make sure my property in Kauai wasn’t missing any of the essentials. Did I need a fire extinguisher? A dead bolt? I figured the safest thing to do was to ask my current insurance provider.

Their answer was a wakeup call: I wasn’t insured as a short-term rental. Any bookings under 7 days were off limits, and my general liability insurance was seriously lacking.

I wasn’t willing to take chances—this was my home, my business, and my guests—so I scrambled for a solution. The light at the end of the tunnel appeared in the form of Darren Pettyjon, Co-Founder of Proper Insurance.

When it comes to specialty insurance, Darren is a wealth of knowledge. He’s spent his entire career working in programs that range from US import bonds to cargo insurance. And now, he and the team at Proper Insurance have put together a policy that’s designed specifically for vacation rentals.

Proper Insurance in Action

The world is unpredictable. And so are your guests. It’s impossible to cover every nitty-gritty scenario, but here are a few situations in which you’d be glad to have Proper Insurance.

    • Your bed bug nightmare comes true. We hope these pesky critters never take up residence at your rental, but if you’re not covered in case of emergency, you’re playing with fire. Proper Insurance offers $15,000 to cover not only the extermination but the lost business income as a result of bed bug infestation.
    • A guest takes an unfortunate spill on a bike you provided. Your policy doesn’t just cover what happens at your rental. It also offers liability insurance for gear like kayaks and bikes, as well as pools and spas.  It extends off the premises.
    • Someone with sticky fingers books your rental.Theft is an unfortunate reality of owning a vacation rental. With Proper Insurance, you’re covered to the full limit of your rental’s contents.
    • You’d like to welcome your guests with a bottle of wine. Proper Insurance removes the liquor liability exclusion, so go ahead and provide a sampling from the local vineyards for your guests to enjoy upon arrival.
    • Your guests throw a party.  Unfortunately, when you entrust your property to someone else, (such as giving the keys to a guest), insurance has limitations. Not with Proper Insurance: from fire to theft to party vandalism, you’re covered.

What is Proper Insurance?

Let’s start by explaining what Proper Insurance isn’t.

It’s not a homeowner’s policy—that doesn’t protect you if a renter damages your home or claims bodily injury.

It’s not landlord insurance, which only applies to on-premise activities and doesn’t cover short-term guests.

It’s not hotel/motel insurance—that’s extremely expensive, and it covers things like refrigerated products and sales samples that vacation rentalists don’t need to worry about.

Proper Insurance takes some necessary elements from all of these policies and builds on them to create coverage that caters specifically to vacation rentals. It protects four specific areas: your property (the building itself), its contents (whatever’s inside), your income (what happens if your property is damaged and your cash flow halts for a year?), and liability (to protect your guests and community, on and off the property).

Who is Proper Insurance for?

Easy: the answer is all vacation rentalists. Anyone who wants to rest assured knowing they’ve protected their property, business, and guests can benefit from Proper Insurance.




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Alanna has been my go-to person as I've navigated the learning curves of running my vacation rental businesses.  She helped...

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Cathy Scott

Alanna has been my go-to person as I've navigated the learning curves of running my vacation rental businesses.  She helped me re-brand my properties, market them effectively, and connect with other valuable industry resources.
Alanna at The Distinguished Guest has been an invaluable resource while setting up my first vacation rental.  I recently bought...

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Alanna at The Distinguished Guest has been an invaluable resource while setting up my first vacation rental.  I recently bought a house in Hilton Head Island and knew nothing about what it takes to be a successful vacation rental.  Alanna has always been willing to lend a helping hand and responds quickly to all of my many questions!  If you're looking to set up a new vacation rental or refresh an existing rental, I would highly recommend contacting Alanna to help out.  She provides a 5 star experience!
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