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How Riley Hotel Group Built A Thriving Key West Collection With roommaster

https://www.youtube.com/watch?v=LY6OC1MhoCM

The Boutique Property Challenge

Riley Hotel Group has built something special in Key West, Florida—a collection of six distinctive bed and breakfast properties that showcase the island's unique charm while delivering exceptional guest experiences. These boutique properties range from intimate 9-room inns to larger 26-room hotels, each with its own character but all unified under Riley Hotel Group's professional management approach. Managing multiple small properties presents unique operational challenges that larger hotels simply don't face. When you're operating a 12-room bed and breakfast, every single booking matters significantly to your bottom line. There's no room for inefficiency, missed opportunities, or operational gaps that might be absorbed by a 200-room hotel's volume.  The complexity multiplies when properties are located within walking distance of each other, as Riley's Key West collection is. Guests might call one property when another has better availability. Groups might need to be split across multiple locations. Without the right systems in place, these scenarios become operational nightmares instead of revenue opportunities.  "We currently have six bed and breakfast hotels located in Key West, Florida, anywhere from 26 rooms all way down to nine rooms—small boutique inns," explains Jen Pekarcik of Riley Hotel Group. The challenge was finding a technology solution that could support this diverse portfolio while enabling the operational efficiency needed for profitability.  

Building on a Unified Foundation

Riley Hotel Group made a strategic decision nearly two decades ago that continues to drive their success today. As they brought each new property under management, they implemented roommaster as their standard platform across all six locations. This was an operational strategy that would define how they compete in Key West's challenging hospitality market.  The decision to standardize on roommaster created immediate operational advantages. Staff could be trained once and work effectively at any property in the portfolio. Management could access consolidated reporting that provided insights across all locations. Guest service standards could be maintained consistently, regardless of which property a guest visited.  "We have been with roommaster with all of them as we've onboarded them onto our management company, and we have loved roommaster's availability when it comes to support," notes Pekarcik. This consistent implementation approach became the foundation for everything Riley would accomplish over the next 20 years.  

Revenue Optimization Through Integration

The real power of Riley's unified approach became evident in their ability to maximize revenue across their property portfolio. With all six properties operating on roommaster, what could have been a coordination challenge became a competitive advantage.  Cross-selling between properties transforms potential lost bookings into captured revenue, "We've been able to cross-sell effectively through the platform with all of our B&Bs located within walking distance of each other. That's also very important," Jen Pekarcik explains. This proximity, combined with unified systems, creates a revenue optimization advantage that individual properties simply cannot achieve on their own.  The integration extends beyond just availability checking. Guests can be strategically placed at properties that best match their preferences while optimizing overall portfolio occupancy. Group bookings can be coordinated across multiple properties. Last-minute availability can be leveraged across the entire collection.

Direct Booking Success and OTA Independence

Small properties face intense pressure from online travel agencies, which can consume 20-30% of revenue through commissions and fees. For boutique properties already operating on tight margins, this expense can mean the difference between profitability and struggle.  Riley Hotel Group leveraged roommaster's Booking Engine functionality to build a strong direct booking channel that reduces their dependence on costly third-party platforms. "Using roommaster Booking Engine has allowed us to drive away from those OTAs to more direct bookings, and it's very effective in doing so," Pekarcik confirms. This direct booking success doesn't just improve profit margins—it also provides better guest data, enables personalized service, and builds stronger customer relationships. When guests book directly, Riley Hotel Group can better understand their preferences, communicate special offers, and create the personalized experiences that keep boutique hotel guests returning.  

Operational Efficiency at Scale

Managing six properties with roommaster creates operational efficiencies that would be impossible with disparate systems. Staff trained at one property can provide backup support at others without system retraining. Inventory management, rate optimization, and reporting can be handled centrally while maintaining individual property identity.  The platform's affordability across multiple properties allows Riley to maintain professional-grade property management capabilities without the per-property costs that could make smaller properties unprofitable. "We definitely have enjoyed the affordability of roommaster along with the fact that we've been able to grow our management company," Jen Pekarcik notes. This cost efficiency extends beyond software licensing. Training costs are minimized when staff work with familiar systems. Technical support is streamlined when all properties use the same platform. Operational procedures can be standardized while allowing for property-specific customizations.  

Competitive Positioning Through Technology

In a market dominated by large hotel chains and vacation rental platforms, Riley Hotel Group's boutique properties compete through personalized service, local expertise, and operational excellence. roommaster provides the technological backbone that enables this competitive positioning while maintaining the efficiency needed for profitability.  The system supports Riley's ability to deliver professional hospitality services while preserving the intimate, personalized experience that defines boutique accommodations. Guests receive the seamless service they expect, while Riley Hotel Group maintains the operational control needed to compete effectively.  

The Strategic Partnership Advantage

Riley Hotel Group's 20-year partnership with roommaster demonstrates the difference between vendor relationships and strategic partnerships. The system that supported Riley Hotel Group's first property has evolved to meet current industry demands, from online booking integration to mobile functionality and beyond.  This partnership approach provides stability that enables long-term planning and growth. Rather than constantly evaluating new systems or managing platform transitions, Riley Hotel Group can focus on what they do best—delivering exceptional guest experiences while building a thriving business.  As Riley Hotel Group continues to expand their portfolio, roommaster stands ready to support their growth with seamless PMS implementation, comprehensive integrations, and thorough training for new team members across future properties  After two decades and six successful properties, Riley Hotel Group continues to rely on roommaster as the operational foundation that enables their success in one of America's most competitive hospitality markets. Their experience proves that independent properties can compete effectively through strategic technology partnerships that understand the unique challenges facing boutique hospitality operators.

The roommaster team have been able and willing to help us make sure all of our things are connected, that all of our channels are working together.

Ryan Allison

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