As the short-term rental industry matures and regulatory pressures mount, many operators are looking beyond traditional vacation rentals to drive long-term growth. Whether it’s scaling property management operations, investing in boutique motels, or pivoting into long-term leasing, today’s savvy operators are finding creative ways to diversify their portfolios.

During Breezeway’s ELEVATE 2025 session “Exploring new markets and inventory strategies for growth”, panelists Jeffrey Lage of StayLage, Lance Stitcher of Seaside Vacations, Kerri Gibson of Chalets Hygge, and moderator Sarah Weaver of Invested Investor, shared their personal stories, strategic shifts, and practical advice for vacation rental managers ready to grow.

Scaling across markets to grow a short-term rental portfolio

For Lance Stitcher of Seaside Vacations, growth didn’t just come from adding more properties, it came from expanding into entirely new markets. From real estate sales to HOAs to STR management, Lance built a multifaceted business by staying open to what the market needed.

His growth strategy? Follow the opportunity. “When we moved into Virginia about 10 years ago, someone reached out and asked if I could sell their house,” Lance recalled. “I said yes, and back then we were the only ones in the region using professional photography, and within three months, we had 30% market share in our primary community.”

Seaside Vacations now manages over 500 properties across two markets in Maryland and Virginia. “The approach in each is very different,” Lance explained. “In Maryland, for housekeeping, we rely almost entirely on contractors, and in Virginia, it’s almost exclusively in-house staff. Last year, we had about 166 employees and another 150 contractors in the loop.”

This market-specific strategy allows Lance to adapt to local labor availability, operational needs, and guest expectations. He emphasized that every market has its own rhythm, regulations, and community dynamics, and operators need to be flexible and intentional when entering new areas.

Pros:

• Reduces risk by spreading operations across multiple markets
• Taps into new guest demand and seasonality patterns
• Allows customization of operations based on local dynamics
• Greater brand reach and business resilience

Cons:

• Increased complexity in staffing, logistics, and compliance
• Requires in-depth knowledge of each market’s regulations and guest profile
• Harder to maintain consistency in guest experience across regions
• Expensive to set up new operational hubs or vendor networks

Investing in boutique hotels to build a sellable business

For Kerri Gibson, diversification was driven by both passion and necessity. Regulatory challenges in Quebec forced her to rethink her short-term rental model and ask: How can I create a sustainable, viable business with less regulatory pressure?

Her answer: boutique motels.

Boutique motels checked all the boxes: alignment with her hospitality values, passion for guest experience, a faster path to cash flow, and a product that could evolve into a brand, not just a set of properties.

“It is two completely different business models and guest expectations,” she noted. “But we’re making it up as we go—and learning fast.”

Pros:

• Opportunity to build a standalone brand that can be sold or scaled
• Less vulnerability to short-term rental regulations
• Growing demand for unique, experiential accommodations
• More financing options for commercial property than residential STRs

Cons:

• High upfront investment for purchase and renovations
• Steep learning curve with hotel-style operations
• Staffing must be more robust (e.g. 100% employees vs. contractors)
• Slower ramp-up depending on renovation timelines

Treating long-term rentals as a separate business

Jeffrey Lage of StayLage shared a critical lesson for operators dabbling in both short- and long-term stays: treat them as separate businesses.

“When we tried to manage them with the same systems, it was chaos,” Jeffrey said. “Once we separated the processes with different operations and different software, it became manageable.”

For his long-term rentals, Jeffrey implements a pre-move-out inspection two weeks before the end of a lease. “It lets us assess the property, give tenants tips to get their deposit back, and plan the turnaround,” he explained. “This way, we’re not losing days of occupancy trying to fix unexpected issues.”

His broader strategy is centered on being nimble. “We’re constantly evaluating: should this be a short-term, mid-term, or long-term rental based on regulations, wear and tear, and profit margins?” he said. “Sometimes, you’re barely making more as a short-term rental. You have to be willing to pivot.”

Pros:

• Steady, predictable income stream
• Less wear and tear on properties
• Easier to scale without constant guest turnover
• Offers a fallback option when STR regulations tighten

Cons:

• Lower gross income potential compared to STRs
• Legal complexities around leases, evictions, and tenant rights
• Longer vacancy periods if units aren’t marketed efficiently
• Harder to deliver "hospitality-grade" experiences if expectations aren’t managed

Diversification isn’t optional, it’s smart investing

For these operators, diversification isn’t a buzzword, it’s how they protect their businesses and position for sustainable growth.

Regulations change. Markets shift. Guest preferences evolve. And the most successful property managers are those who adapt.

Jeffrey summed it up best: “Be open to yes. Then figure out why you might say no after the fact. Ask good questions. Stay curious. That’s how we’ve expanded into multiple states and continued to grow.”

Whether you’re a small operator looking to grow or a seasoned manager facing new market challenges, this message is clear: the future of vacation rental success lies in flexibility, creativity, and building businesses that can thrive beyond short-term stays.

View all of the expert resources shared during ELEVATE 2025 and the full session recordings to continue elevating your property operations.