City of Bend

License Required: Yes

Bend requires a Short-Term Rental License from the City’s Development Services department. As of 2024, Bend permits both owner-occupied and non-owner-occupied STRs, but the two categories have different rules and the owner-occupied category has been more stable politically.

Key requirements: License application (~$75–$150 fee), proof of adequate liability insurance (typically $1M), compliance with noise, parking, and occupancy standards, and collection/remittance of Transient Room Tax (TRT) to Deschutes County. Licenses must be renewed annually.

Bend’s STR ordinance has been a recurring political topic — there have been multiple proposals to cap non-owner-occupied licenses in certain zones. Before purchasing a non-primary-residence STR in Bend city limits, verify the current status of any pending ordinance changes.

Sunriver (Deschutes County / SROA)

SHARC Permit Required: Yes

Sunriver operates as a private resort community governed by the Sunriver Resort Owner’s Association (SROA). STR operators must obtain a SHARC Permit ($300–$350/year as of 2024), which grants guests access to SHARC — the community’s aquatic and recreation center. Without SHARC access, your listing loses one of its most compelling amenities.

Additionally, Sunriver falls under Deschutes County jurisdiction for TRT collection. There is no county-level STR permit requirement separate from the SHARC permit, but all STR income must be reported and TRT remitted.

Caldera Springs (the newer premium enclave within Sunriver) has its own HOA overlay with additional STR rules that have changed multiple times. Confirm with Caldera Springs HOA directly before any purchase with STR intent.

Sisters (City of Sisters)

License Required: Yes — with Community Cap

Sisters has implemented a community-wide cap on STR licenses. As of 2024, the number of allowed STR licenses in the city limits is limited, and the waitlist to obtain a new license can be significant. Sisters is a highly desirable STR market (proximity to ski resorts, Sisters Rodeo, wildflower season), which drove demand and prompted the community cap.

If you’re purchasing in Sisters with STR intent, verify whether an existing license can transfer with the property — sometimes it can, which dramatically affects property value and investment calculation. Some Sisters properties are marketed specifically as “grandfathered STR” — verify this claim independently before any offer.

La Pine (Deschutes County Unincorporated)

County TRT Compliance Only

La Pine is largely unincorporated Deschutes County, which means county-level TRT compliance is required but there is no specific STR permit or license required as of 2024. This makes La Pine one of the most permissive STR environments in Central Oregon — a significant factor in its investment appeal. Cascade Lakes and Wickiup Reservoir access, combined with minimal regulatory friction, creates a strong value-to-return ratio for STR investors.

Regulations can change in unincorporated areas. The Deschutes County Board of Commissioners has discussed broader STR rules multiple times. Monitor county policy if you’re building a La Pine investment thesis.

Redmond (City of Redmond)

License Required: In Process

Redmond has been developing its STR ordinance. As of late 2024, Redmond requires a business license for STR operators and TRT compliance, but the full licensing framework is still evolving. Redmond’s STR market has been growing rapidly alongside its real estate appreciation — expect clearer ordinance structure in 2025.

Terrebonne, Madras, Prineville (Unincorporated / Small Cities)

Minimal Regulation — County TRT Applies

These communities sit in Jefferson and Crook County or unincorporated Deschutes County, and STR regulation is minimal. County TRT applies across all of them. Jefferson County (Madras, Metolius) has its own TRT structure separate from Deschutes County. Crook County (Prineville) similarly. Verify the specific county requirements before operating.

Transient Lodging Tax: Every Community

Regardless of where your STR is located in Central Oregon, you are required to collect and remit Transient Lodging Tax (TLT) on all rental income. Deschutes County’s TLT rate is 9.8% (as of 2024). Jefferson and Crook Counties have their own rates. Most major platforms (Airbnb, VRBO) collect and remit TLT automatically in Oregon — verify with your platform and confirm with the county what you’re responsible for remitting directly.

HOA Restrictions: The Wild Card

Even in permissive jurisdictions, many Central Oregon neighborhoods have HOA CC&Rs that restrict or prohibit STRs. This is especially common in newer Bend subdivisions, some Sunriver sub-associations, and gated communities. Always review the full CC&Rs before closing on any property with STR intent. A restriction buried in Section 14 of a 40-page CC&R document can eliminate your investment thesis entirely.