The Growing Trend: From Nightly Guests to Year-Round Residents
Over the past few years, short-term rentals like Airbnb and VRBO have exploded in popularity, especially in high-demand Oregon markets like Bend and Eugene. These platforms gave property owners an opportunity to earn strong nightly rates, especially during peak tourist seasons. But in 2025, we’re noticing a shift: more and more owners are transitioning their properties from short-term rentals into stable, long-term housing.
At Pioneer Property Management, we’ve seen this firsthand. This summer alone, we’ve helped several owners successfully convert their homes into 12-month rentals—and the trend doesn’t appear to be slowing down.
Why the change? While every owner’s situation is unique, several common themes are emerging that are worth exploring.
Why Owners Are Making the Shift
1. The Desire for Consistent, Predictable Income
Short-term rentals can generate high returns, but they’re unpredictable. Income depends on constant bookings, fluctuating nightly rates, seasonal demand, and ongoing competition. For many owners, this unpredictability is stressful—especially if they rely on the property as a source of stable cash flow.
By moving to a long-term rental model, owners enjoy steady monthly rent. Even during slower seasons, the property continues to generate consistent income without the highs and lows of vacation rental markets.
2. Less Turnover, Less Hassle
Managing a short-term rental is essentially running a hospitality business. Guests check in and out every few days, requiring frequent cleaning, restocking, and maintenance. For owners who self-manage, this can become overwhelming. Even with a management company, the costs of turnover and upkeep add up.
Long-term rentals, on the other hand, offer stability. Tenants typically stay for 12 months or longer, meaning far fewer turnovers. This not only reduces wear and tear on the property but also lowers operating costs for the owner.
3. Market Trends Favoring Long-Term Rentals
In Bend, Eugene, and across Oregon, long-term rentals are in high demand. Vacancy rates remain low, and renewal rates are high. That means owners who convert their properties often find it relatively easy to attract quality residents.
For those who once relied on tourists and travelers, this trend offers peace of mind: a deep pool of prospective long-term renters is ready and waiting.
4. Regulatory Pressures on Short-Term Rentals
Cities across the country are tightening regulations on short-term rentals. Licensing requirements, occupancy taxes, and restrictions on how many nights a property can be rented are becoming increasingly common. In some markets, entire neighborhoods are limiting or banning vacation rentals.
Switching to a long-term lease structure helps owners sidestep the ever-changing regulatory environment and operate within a more predictable, less restrictive framework.
How Pioneer Makes the Transition Seamless
Transitioning from a short-term rental to a long-term one isn’t as simple as flipping a switch. Owners need a thoughtful process to ensure their property is positioned for success. That’s where we come in. At Pioneer Property Management, we guide owners step-by-step through the transition:
1. Market Rent Analysis
We begin by reviewing current market conditions and comparable rental properties. This helps owners understand what they can realistically expect for monthly rent. While nightly short-term rates may look higher, steady monthly rent combined with reduced costs often results in a more reliable bottom line.
2. Setting Owner Expectations
Switching models means rethinking the property’s purpose. Instead of guest-ready furniture and amenities, the focus shifts to functionality for long-term living. We walk owners through what adjustments may be needed—from removing personal items to making minor updates that appeal to residents.
3. Resident Placement
Finding the right residents is key to success. Our team handles the full leasing process, including marketing the property, screening applicants, and drafting lease agreements in compliance with Oregon law. We prioritize qualified tenants who are likely to renew and treat the home with care.
4. Ongoing Management & Support
Once the home is leased, we handle everything from rent collection and maintenance coordination to renewal discussions and compliance issues. Owners no longer need to worry about bookings, guest turnover, or managing cleaners. Instead, they can step back knowing their property is well taken care of.
The Benefits Owners Are Seeing
The owners we’ve worked with this year to transition from short-term rentals to long-term housing have reported:
Peace of Mind: No more stressing about last-minute cancellations or unbooked nights.
Lower Costs: Fewer turnovers mean reduced cleaning, repair, and furnishing expenses.
Better Work-Life Balance: Owning a long-term rental feels less like running a hotel and more like a straightforward investment.
Satisfied Residents: Tenants who view the home as their own create stability and care for the property.
In fact, many owners told us they wished they had made the move sooner.
Is Now the Right Time for You?
If you’ve been wondering whether to pivot from a short-term rental to a long-term lease, you’re not alone. The increased interest we’re seeing across Bend and Eugene tells us this isn’t just a one-off decision—it’s a trend.
With low vacancy rates and strong demand for long-term rentals, now is an excellent time to explore the idea. Even if you’re not ready to make the switch immediately, reviewing your options ensures you’re prepared for what the market may bring.
Final Thoughts
Short-term rentals aren’t going away, and for some owners, they’ll remain the best option. But for many others, the stability and predictability of long-term leasing outweigh the unpredictability of the vacation rental market.
At Pioneer Property Management, we specialize in making that transition smooth, stress-free, and profitable. Whether you own a condo in downtown Eugene, a home near the Deschutes River in Bend, or a suburban property anywhere in between, we’re here to help you evaluate your options.
If you’d like to learn more about what this process looks like, reach out to our team. We’d be happy to walk you through the numbers, the steps, and the potential outcomes.
