VP of Vacation Rentals

Position Summary

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

Success requires someone who moves quickly, takes initiative, and thrives in a fast‑paced, evolving environment.

• 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 of service across all properties and guest touchpoints
• Uphold brand standards and reinforce a culture of accountability and responsiveness

• Support business development efforts and contribute to portfolio growth initiatives
• Partner with internal teams to ensure successful onboarding and integration of new properties
• Act as a brand ambassador for the Seven Keys destinations and services

• Set the standard for professionalism, communication, and execution across the organization
• Foster a culture of accountability, urgency, and results‑driven performance
• Motivate and influence teams across multiple locations to align with company goals

• High School Diploma or equivalent
• 7+ years minimum prior vacation rental / short term rental experience
• 5+ years minimum leadership experience
• Florida real estate management experience
• Experience with property management software required;
  Streamline preferred
• Valid driver's license
• Ability to pass pre‑employment testing which may include drug testing and/or background screening
• Must have proficiency with Microsoft office suite including Excel, Word, PowerPoint and Outlook and additional ability to learn and excel at new software programs
• Proficiency in written and verbal communications to multiple stakeholders both internally and externally
• Exceptional interpersonal skills with the ability to make and cultivate strong personal connections and relationships with homeowners utilizing skills such as:
• Timely and thorough follow‑up
• Active listening
• Proactivity
• Adaptability
• Problem solving
• Keen attention to detail and desire to act to uphold luxury service expected by homeowners and guests
• Commitment to providing outstanding customer service
• Well‑developed administrative and organizational skills demonstrated in ability to manage time effectively and meet deadlines in a fast‑paced environment
• Team player mentality with a willingness to be flexible and open to feedback and continued growth
• Ability to be flexible and work in a fast‑paced environment with hours of work varying, especially during peak season

Annual Salary: $110,000 - $150,000 depending on experience

• Bonus plan is based on both personal and company goals

• Paid time off such as PTO, sick days, and vacation days
• Health, Dental and Vision insurance
• Retirement benefits or accounts
• Car allowance

• Full‑time;
  This role will require in‑office responsibilities in our Key West and Marathon offices.