One of the biggest mistakes I see people make when they decide to start an Airbnb is getting excited and immediately jumping into property searches.

Honestly, I thought that way too.

Find a house.

Buy it.

Furnish it.

List it.

Start making money.

Simple, right?

Not exactly.

Before you ever call a Realtor or schedule a showing, there’s something much more important you should do first:

Find out whether you can legally operate a short-term rental in the community you’re considering.

Because falling in love with the perfect property only to discover you can’t legally use it as a short-term rental can be a heartbreaking—and expensive—lesson.

Every city, county, and community has different rules.

Some welcome short-term rentals. Others heavily regulate them.

Depending on where you’re looking, you may encounter:

• Permit or licensing requirements
• Neighbor notification requirements
• Waiting lists
• Occupancy restrictions
• Parking requirements
• Limits on the number of STR permits
• Spacing or density requirements
• Primary-residence requirements
• Specific zoning restrictions

Some communities allow STR permits to transfer when a property is sold. Others require the new owner to start the application process from scratch.

And some communities may not be issuing new permits at all.

The rules can change dramatically simply by crossing a city or county boundary.

That’s why I believe your first step shouldn’t be finding a house.

Your first step should be finding a community where your short-term rental business can actually operate.

Before I seriously started shopping, I spent a lot of time researching potential markets.

I wanted answers to questions like:

• Are short-term rentals allowed?
• Do I need a permit?
• Are new permits currently available?
• Is there a waiting list?
• Does the permit transfer when the property is sold?
• Is neighbor notification required?
• Are there occupancy restrictions?
• Are there parking requirements?
• Are there quiet hours?
• Are there spacing or density requirements?
• Are there zoning restrictions?
• What lodging or occupancy taxes are required?

I wanted those answers before I fell in love with a property.

And I’m glad I did, because I almost researched the wrong rules.

Initially, I thought I would need to notify all the surrounding neighbors and go through an approval process.

That’s what I had learned while researching Bend.

But then I dug deeper.

Our property wasn’t actually located inside Bend city limits.

It was in the Three Rivers community in unincorporated Deschutes County.

That distinction changed everything.

The rules I had been researching for Bend didn’t apply to the property we were considering.

Had I simply assumed “Bend area” meant “City of Bend,” I could have wasted a tremendous amount of time researching requirements that didn’t apply to us.

That experience reinforced one of the biggest lessons I’ve learned throughout this entire process:

Never assume. Verify.

The mailing address, closest city, tourism market, and actual government jurisdiction aren’t necessarily the same thing.

When you’re researching an STR property, you need to know exactly which government entity makes the rules for that specific address.

Google is great.

Facebook groups can be helpful.

Other Airbnb hosts can share valuable experiences.

But none of those replace talking to the people who actually administer and enforce the rules.

Depending on the property, that could mean contacting:

• City planning departments
• County planning departments
• Business licensing departments
• Community associations
• HOA management companies

Take notes.

Ask questions.

Verify everything.

And if you’re still unsure, ask again.

Regulations change. Websites aren’t always updated immediately. And what applies to a property across the street may not necessarily apply to yours.

When you’re making an investment this large, it’s worth making a phone call.

Here’s another assumption that could become expensive:

The property is already operating as an Airbnb, so I can keep operating it as one after I buy it.

Maybe.

But don’t assume it.

Just because a property currently operates as a short-term rental doesn’t mean its permit automatically transfers to a new owner.

Some permits transfer.

Some don’t.

Some communities require an entirely new application.

Others may have caps or waiting lists that could make obtaining a replacement permit difficult—or impossible.

So even if you’re buying an established vacation rental with bookings, reviews, furniture, and an existing Airbnb listing, verify the permit situation directly with the city or county.

The current owner’s ability to operate the property doesn’t automatically guarantee yours.

As a Realtor, I originally thought my rental near Pacific University in Forest Grove could make a great short-term or mid-term rental.

And the logic makes sense.

College towns can have built-in demand from:

• Parents visiting students
• Graduation weekends
• Sporting events
• Alumni events
• Conferences
• Campus tours
• Temporary housing
• Medical and business travel

In Oregon, communities such as Eugene, Corvallis, Portland, Forest Grove, Newberg, and McMinnville all have universities or colleges that can help generate recurring visitor demand.

But strong demand doesn’t guarantee permissive STR rules.

College towns can also be sensitive to housing availability, neighborhood impacts, parking, and the conversion of long-term housing into vacation rentals.

Once again, the lesson comes back to the same thing:

Research the community before you research the house.

Once you’ve determined that a community works for your goals, then it’s time to start shopping.

At that point, your Realtor can help you evaluate things like:

• Neighborhoods
• Property values
• Comparable properties
• Maintenance concerns
• Furnishing and renovation needs
• Potential operating costs
• Amenities
• Resale considerations

If you’re working with a Realtor who understands investment or vacation properties, they can also help you identify questions you may not have considered.

But before you start touring houses, make sure the business you’re planning to build is actually allowed there.

Once you’ve narrowed down your potential communities, Airbnb itself becomes a valuable research tool.

Before buying, I spent countless hours studying other listings.

I looked at:

• Nightly rates
• Availability
• Reviews
• Amenities
• Hot tubs
• Guest capacity
• Outdoor spaces
• Photos
• How properties were marketed

I wasn’t just looking at what other hosts charged.

I wanted to understand what guests seemed to value.

What did successful properties offer?

What amenities appeared repeatedly?

What did guests rave about in reviews?

What were they complaining about?

That research eventually influenced many of the decisions we made with The Cabin on the Canal.

Legal permission to operate an Airbnb is only the beginning.

Before buying, you also need to ask yourself:

Can I actually afford this?

Who will clean it?

Who will handle maintenance?

Who will maintain the hot tub?

How far away is the property?

What happens when something breaks at 9 p.m.?

What systems will I need?

How much will furnishing cost?

How much money should I keep in reserve?

And perhaps most importantly:

How much time am I willing to devote to this business?

Because make no mistake.

This isn’t passive income.

It’s hospitality.

And hospitality takes work.

✓ Research communities before properties.

✓ Determine the property’s actual city or county jurisdiction.

✓ Never assume an existing STR permit transfers with the property.

✓ Verify rules directly with the agencies responsible for enforcing them.

✓ Understand that regulations can change.

✓ Study existing Airbnb listings to understand your competition and your guests.

✓ Don’t fall in love with a house before knowing whether you can legally operate it as a short-term rental.

✓ Remember that you’re building a business—not just buying a property.

The house is the exciting part.

But the research you do before you ever walk through the front door may be what ultimately determines whether your short-term rental succeeds.

Thinking about investing on the Oregon Coast, around Mt. Hood, in Central Oregon, wine country, or another Oregon community?

Before you shop, research the rules first.

➡️ View our complete guide to Oregon communities and their short-term rental rules, permits, licensing requirements, maps, and other resources.

Oregon Coast STR Communities – Official Rule Pages

Tanya Peterson is a REALTOR® and Principal Real Estate Broker with Next Level Real Estate PNW at John L. Scott Market Center. With more than 20 years of experience, she serves Forest Grove, Washington County, Oregon wine country, and surrounding Portland Metro communities.

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TanyaPeterson.Realtor | 503-260-2164
Equal Housing Opportunity.