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Dispatches from the road: To Airbnb or not to Airbnb

October 21, 2022

In his most recent dispatch, Courthouse News’ western bureau chief mulls the effects of short-term rental regulations from Hawaii to Maine.

Chris Marshall

By Chris Marshall

Western Bureau Chief for Courthouse News Service since 2014. San Francisco Federal Reporter and Northern California Bureau Chief from 2006 to 2014. Passionate about photography, camping and history.

Two days before a flight to Maui, my would-be Airbnb host cancelled the reservation. Confronted by her building manager for renting out her condominium in violation of a strict local ordinance, she claimed it wasn’t her fault, she couldn’t do anything about it.

Other than not rent out her condo illegally in the first place, of course.

Based on the number of positive reviews, she had been getting away with her scheme for years. I suppose it’s possible she bought the unit before any regulations went into effect. Maybe she had applied for a license but didn’t get one. Or perhaps she decided to make as much money as she could before getting caught.

My point is not to complain about one scofflaw. I managed to find a nice — if more expensive — place to stay that I confirmed was legal before booking. That visit featured a road trip around the island, excursions to multiple Maui Brewing Co. locations and ample beach time.

Colorful murals like the one pictured here in May 2022 dot businesses in downtown Hilo on the Big Island of Hawaii. (Chris Marshall / Courthouse News)

And I’ve enjoyed stays at many other (legal) Hawaii vacation rentals before and since.

At the Hilo Bay Hale, between stuffing us with local eggs and fruit from a jungle farm his husband tended, our host Matthew talked to my boss and I about local geology, the effect of climate change and, of course, where to go in Hilo town, a short walk down the hill.

On a subsequent trip to the farmhouse, I passed jungle roads and a suburban neighborhood that could have been in any number of areas on the mainland before ending up at the quirky vacation rental down the end of a driveway lined with overgrown tropical flora. Flush with rustic charm, the electricity could use some updating, as shown by the fried charger for my laptop.

In town for work earlier this year, I stayed at a dated hotel in touristy Waikiki that — like many others — tacked on significant “resort fees,” before heading to the Big Island for a long weekend at an Airbnb within walking distance of Magic Sands Beach.

Down the road from bustling but mercifully small Kailua-Kona, Magic or Disappearing Sands Beach is named because high winter surf tends to carry the sand away, sometimes overnight, revealing the dark lava below.

Known as Magic Sands Beach or Disappearing Sands because high winter surf tends to carry the sand away, sometimes overnight, revealing the dark lava below, the area officially known as White Sands Beach — pictured here in May 2022 — is frequented by tourists and locals alike. Just down the road from bustling Kailua-Kona, a restaurant with attached bar provides views of sometimes stunning sunsets. (Chris Marshall/Courthouse News)

Not missing a beat from picking fruit from a large tree in his yard, one of the hosts invited me to use the grill or any of the beach gear stacked along the edge of the courtyard. His wife arrived after me with their young children, who ran up the steps to their second-floor apartment. My unit included a well-stocked kitchen and a separate bedroom. Large ceiling fans and cool ocean breezes kept the temperature down.

Short-term rental ordinances in Hawaii are complicated, vary not only between but within the islands and are constantly evolving. The term means something different depending on where you are. Licensed bed and breakfasts are subject to different regulations.

A federal judge recently blocked a rule that would prohibit rentals under 90 days outside areas zoned for resorts on Oahu. While allowing rentals in more areas, Maui no longer accepts applications to convert properties to short-term rentals. A legal challenge to updated regulations is pending.  Kauai allows short-term rentals only in a few small hotel districts while grandfathering in older units. On the Big Island of Hawaii short-term rentals-defined as 30 days or less-are allowed if the owner lives on site but otherwise restricted.

I said it’s complicated. And maybe it should be.

One of five parks named after a Civil War veteran, Honolulu, Hawaii’s Fort DeRussy’s green canopy and grassy areas stand in stark contrast to the surrounding high-rise condominiums, hotels and shopping areas that make up most of the Waikiki tourist district, pictured here in May 2022. (Chris Marshall/Courthouse News)

Over sushi in suddenly hip Portland, Maine, a couple months back I discussed a local referendum with my brother — a former City Council member — that, among other things, would outlaw vacation rentals on properties where the owner doesn’t live.

While such restrictions could alleviate a housing crunch in many densely populated neighborhoods in the increasingly expensive city, he argued they could shatter the market for rental properties on the many islands that dot Casco Bay where non-resident owners have been welcoming summer vacationers since long before Airbnb was a thing.

The new ordinance could leave their houses unoccupied year-round, reducing their income, eliminating a steady stream of tax revenue and hurting island businesses while doing little if anything to help the housing situation. Not exactly the goal.

When it comes to vacation rental regulations, one size might not fit all.

Stately brick buildings line a leafy side street in this September 2017 photo from Portland, Maine’s West End neighborhood. (Chris Marshall / Courthouse News)

Growing up in Maine I never missed the summer lobster eaters and autumn leaf peepers once they left, but I recognize my already poor home state would have been worse off without them.

As a visitor I like to immerse myself in a location, walking the streets, going to the local restaurants and stores while staying in the neighborhoods.

But too many rental properties can disturb residents and detract from exactly what attracts visitors in the first place. Not to mention some vacationers are jerks. When your neighbors are all tourists, you might as well be in Waikiki.

Regulations should include input from and aim to retain long-term residents while rewarding responsible hosts and taking local factors into consideration. But who gets to decide?

Did I mention it’s complicated?

Diamond Head beckons in the distance in this February 2015 shot from the beach at Waikiki in Honolulu, Hawaii. (Chris Marshall/Courthouse News)

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