Short-Term Rental Rules in Redmond, Oregon: What to Check Before You Buy

I'm Holli Cobb, a REALTOR® with REAL Broker in Redmond, and I get a version of the same question from investors looking at a short-term rental: can I actually run one here. It's a fair question, and it's a different question than whether a property would make a solid long-term rental. A house can pencil out beautifully as a nightly rental on a spreadsheet and still not be allowed to operate as one, depending on where it sits and what governs it.

Whether short-term rentals are allowed on a given property is a zoning and permitting question, decided by the city of Redmond or Deschutes County depending on exactly where the property sits, not something a listing description or a prior owner's say-so settles. Rules in this space tend to change over time as cities and counties respond to housing pressure, so what a neighbor down the street has been doing for years isn't proof that a new buyer can do the same thing going forward. The only reliable answer comes from the planning department itself, checked against the specific parcel, before you're under contract.

Even on a property where the city or county permits short-term rentals, an HOA's own CC&Rs can prohibit them outright or cap how many units in a community can run that way, the same kind of restriction I cover in HOA vs. No HOA. Two layers of rules have to both say yes, the jurisdiction and, if there is one, the HOA, and a buyer who checks only one of them is the one who finds out the hard way after closing.

A short-term rental's income depends on occupancy and nightly rate, both of which swing with the season and with how actively the property is managed, not a flat monthly check from one tenant. That makes the cash-flow side of the analysis genuinely different from the long-term comparison I walk through in Cap Rate vs. Cash Flow, and it usually means either real time spent managing bookings and turnovers yourself or a cut paid to someone who does, closer to the trade-offs in Property Manager or Self-Manage. Run both the permission question and the real cost of running it before you compare it against a long-term rental on the same property.

Confirm short-term rental use is permitted for the specific parcel with the city of Redmond or Deschutes County planning department, in writing, rather than assuming based on the area or what a listing claims. If there's an HOA, get the actual CC&Rs and ask directly whether short-term rentals are allowed and whether there's a cap already in use. Only once both of those come back clear does it make sense to build out the income side of the analysis. If you want help running down the permission question on a specific property, get in touch and we'll work through it together.