The challenge of scaling up: Women in short-term rentals

Worldwide: Lisa Roads, CEO of The Holiday Property Coach, and Daniela Derin, co-founder of Skol Apartments Marbella, share their experiences as women scaling in the STR industry and offer solutions to help other women overcome barriers.

As the global STR sector continues to gain momentum, scaling an STR business in 2025 remains a formidable challenge. For many women, the path to growth is even more daunting. Barriers such as limited access to funding, a lack of awareness around available resources, imposter syndrome, and gender bias continue to hold many back.

Lisa Roads, CEO of The Holiday Property Coach, understands these struggles all too well. With over 25 years of experience in property marketing, ownership, and management, Roads has learned how to start, operate, and scale a successful STR business. However, her journey has been far from easy. Throughout her career, Roads often found herself as the only woman in managerial positions, feeling excluded in male-dominated spaces. She recalls moments where she had to filter her words or alter her appearance, which left her feeling disheartened.

The challenges Roads faced motivated her to establish the ‘Women in Short-Term Rentals’ community in December 2024. The community was designed to help women in the STR sector overcome the same barriers she encountered. Roads explained: “We needed a funnel, a space where women could build confidence, make connections, and recognise the value of attending these events. When you walk into a big summit not knowing anyone, it’s daunting. I’ve been in this industry for a long time, and even I’ve felt overwhelmed.”

Roads emphasised that the community is not about excluding men but creating a space where women can feel comfortable being their authentic selves. “It’s about being able to ask for support, open up, and show vulnerability,” she said.

Another woman who can relate to these challenges is Daniela Derin, co-founder of Skol Apartments Marbella. With 27 years in the STR business, Derin has experienced firsthand the struggles women face when scaling their businesses.

“A lot of women don’t believe in themselves or their abilities,” Derin said. “But soft skills like resilience and trusting yourself really helped me. I’ve always had high self-esteem,  I never felt people saw me differently because I’m a woman, and I’ve never doubted my capacity to grow and scale, which helped me in the long run.”

These same qualities are central to the ‘Women in Short-Term Rentals’ community, which focuses on offering advice, support, empathy, and practical insights, empowering women to scale their businesses with confidence.

For Roads, the lessons shared within her community extend beyond personal development, they also relate to how operators should treat their guests. “Hospitality hasn’t changed much. It’s still about people. Women get that,” she said. “It’s not just about scale and shareholder returns. It’s about caring for your guests, building trust, and fostering long-term relationships. That’s what sets us apart.”