VP of Rentals; Key West

Seven Keys Vacations is a locally led vacation rental management company serving the Florida Keys, with offices in Key West and Marathon and homes throughout Key West, Key Largo, Islamorada, Marathon, Big Pine Key, and the Lower Keys. Our portfolio includes oceanfront homes, canal-front retreats, condos, pet-friendly rentals, and properties with private pools and boat docks — giving owners and guests a wide range of high-quality options across one of Florida's most iconic coastal destinations.

We are led by a team with decades of combined experience investing in, growing, and operating successful vacation rental management companies. That experience is paired with on-the-ground local managers who live in the markets they serve and have the authority to make decisions in real time. We believe vacation rental management is fundamentally a relationship business, and relationships are built locally.

For homeowners, we are an advocate first — focused on protecting the home, maximizing income, and delivering transparent, real-time reporting. For guests, we deliver professionally cleaned, fully equipped homes backed by reliable local support from check-in to check-out, helping make every Florida Keys vacation simple, friendly, and stress-free. From quick weekend getaways to monthly stays, from Key West's historic streets and sunset celebrations to the world-class fishing, diving, and boating of the Upper and Middle Keys, Seven Keys Vacations brings local expertise and professional management to every stay.

Seven Keys Vacations is a proud franchisee of Casago, North America's largest specialized vacation rental manager.

Seven Keys Vacations is seeking a VP of Rentals to lead and scale rental performance across a growing, multi-market portfolio. This is a high-impact, hands-on leadership role responsible for driving results across homeowner relationships, rental operations, and service delivery. You will partner directly with ownership and General Managers to bring structure, accountability, and consistency to the rentals function - while ensuring teams are aligned, supported, and performing at a high level.

Success in this role requires someone who moves quickly, takes initiative, and thrives in a fast-paced, evolving environment. You will be responsible for building and refining systems that improve efficiency, elevate the homeowner and guest experience, and enable the organization to scale with confidence. You’ll operate across multiple coastal markets, stepping in where needed to solve problems, remove friction, and keep operations moving forward.

This role is ideal for a leader who combines strong relationship instincts with operational discipline, and who takes pride in turning complexity into clarity.

• Serve as the primary point of contact for key homeowners, ownership, and internal teams
• Build and maintain strong homeowner relationships, proactively managing expectations, revenue goals, and satisfaction
• Address and resolve homeowner concerns quickly and effectively, ensuring trust and retention
• Communicate consistently and transparently with stakeholders across all markets

• Partner with General Managers to drive consistency and accountability across the full rental lifecycle
• Oversee onboarding of new homeowners, ensuring a seamless transition into management
• Ensure alignment and performance across reservations, guest services, and frontline teams
• Collaborate with the VP of Operations to maintain service quality across housekeeping, maintenance, and vendor performance

• Develop and implement standardized processes that bring structure and clarity to rental operations
• Utilize company systems and data to identify trends, improve performance, and drive informed decision-making
• Continuously refine workflows to improve efficiency, communication, and scalability across multiple markets

• Act as the escalation point for complex guest and homeowner issues, resolving challenges with urgency and professionalism
• Ensure a consistently high standard…