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Simply Vacation Rental Management

Know what a rental could earn
before you buy it.

Tell us what you’re working on and ask for a free investment analysis.

Guests rate our Mt. Hood homes 4.84 out of 5 this year, and 88% of their reviews are five stars.1

Listing photo: inside the A-frame, a living room with a spiral stair and tall windows onto the forest
A-frame · Rhododendron

Each drawing is one of our homes. The small photo is its listing.

Can it be rented short-term?

Portland requires a short-term rental permit. Both types need a resident who lives there 270+ days a year, so a home no one lives in does not qualify.

Type A
Up to 2 bedrooms.
Type B
3 or more bedrooms, and a conditional use review.

Mt. Hood and the Gorge follow their own county and city rules. Check those too.

Will the tax math work?

For high earners who qualify, cost segregation and bonus depreciation can turn a short-term rental into a large first-year deduction against W-2 or business income. It depends on two tests and on your CPA.

See the tax rules, with one example

Request a free investment analysis