12 Oregon STR Sales in 12 Months: AirBNB Investment Insight and Outlook in 2025-2027

[AJ Wong]

For context I have assisted over a dozen investors (including myself!) acquire zoned and frequently active turn-key or licensable vacation rentals ranging from $200K-$2M on the Oregon Coast and beyond in the past year (30+ in the past 3) - so I wanted to share some insight that may help investors manage expectations for vacation rental investment as demand expectedly intensifies with the extension of the STR Tax Loophole.

Here are my insights into the Oregon Coast STR market (from Brookings to Astoria and beyond) and looking forward two years through the end of the 100% bonus depreciation allowance:

- The barrier to entry will continue to grow. If the next few years are anything like the past seven, acquiring a turn-key vacation rental might be the only option. At present - a healthy percentage of client investments are homes that were not actively utilized as AirBNB's but were eligible through city or county permissions. Each county and city has their own requirements - but many often include saturation, density or distance requirements between active rentals. As difficult as it is to identify permissible STRs in 2025 - the likelihood is that many of the zones and homes that currently qualify - might not in the near future. On a positive - local and often small municipalities have done an excellent job (in my opinion) of fairly regulating most regions to prevent over saturation and clear processes to permit issuance and operations. 

- Low inventory to remain so. I often say that Oregon Coast Real Estate sells itself - especially when it's a lucrative vacation rental, but actually securing one is another task entirely...The Oregon Coast features 363 miles of majestic coastline but the majority is remote, rural and underdeveloped. That's part of what many love about it, but also what makes it difficult to find a 'winner.' For example: $650K budget, ocean view, 3+ bedrooms, furnished and STR eligible...maybe there are 5-6 genuine prospects at any given moment. Average TOTAL STR inventory including all operating or licensable STRs of single family, townhomes or condos on a given day is 100-150 maximum! That's a small neighborhood in some popular destinations.

- Permitting and Licensing is straightforward. Finding an STR is difficult but once you do - it is usually a very direct application with reasonable relative fees and costs (more on that below.) This is an area of emphasis for all STR investors (regardless of where) and we try and identify active STRs within 24 hours of them coming to market - or our clients risk the chance of missing the opportunity to tour and offer due to competitive demand. There have been no instances or examples of properly permitted or licensed properties that renewed on time with licenses being invalidated. To the contrary - many cities have instituted CAPs or maximum STRs that protect investor participation.

- Operational costs are often lower. I've supported STRs investors in a variety of seasonal regions including the SoCal desert areas of Joshua Tree, Palm Springs and Indio. Although often on a production to value ratio - successful SoCal STRs can generate higher gross production (sometimes double!) the ROI or cash on cash return is sometimes identical (depending on the property.) For example an optimized $750K Palm Springs/Indio STR might generate $125-150K in gross annual revenue but after the double digit occupancy taxes, property taxes, insurance and utilities, the actual ROI could be similar to a similarly valued home on the coast generating $75-80K. How? Lower taxes, insurance, utilities and general operational and management costs. Our most recent investment is a riverfront 1K/SF cottage on two acres..without flood insurance and property insurance is $1100/yr. Well. Septic and $75/electricity.

- Income Outlook & Appreciation. While I do not have a crystal ball, I can tell you that the Oregon Coast is an increasingly popular domestic destination with surprisingly under-serviced accommodations. There are very few 4&5 star hotels, and in season, good luck finding any room on short notice. Overall, I'm actively investing on the Oregon Coast as I'm still often surprised at 'what you get for the money' even in today's market. In my humble opinion (and I recognize the environment is not for everyone) Oregon Coastal towns offer some of the strongest overall beach value in the country. As an example - my most recent oceanfront closing was a turn-key 3/3 STR for under $900K - out of the flood zone.

- Areas of Interest. Whole-heartedly I think STR success is achievable anywhere (with a long term game-plan) and there are investable STR opportunities along the entire Oregon Coast. The first qualifier is often zoning, licensing or permitting but depending on the search criteria - there are properties and terms that will consistently reach or exceed 10-20% C.O.C (cash on cash returns). Some highlight areas to keep an eye on are: Brookings, Bandon, Florence, Waldport, Rockaway Beach, Pacific City, Seaside, Tillamook County, Manzanita, Mt Hood, Crater Lake area and the wine region of Willamette Valley.

Summary: This dozen deals took nearly 25,000 miles on the road, three tours per offer, dozens of bids, and hundreds of evaluations and Pro Formas. Going forward, successful STR investing will demand even more efficiency, strategy, and persistence — but for those who get it right, the rewards are only growing.