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 Vacation 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.
Homeowner Relations & Portfolio Performance
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
Rental Operations Leadership
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
Systems, Process & Scalability
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
Issue Resolution & Service Excellence
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
Business Growth & Market Support
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 entire Seven Keys destinations and services
Leadership & Culture
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
$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
Schedule
Full-time; This role will require in office responsibilities in our Key West and Marathon offices.
Homeowner Relations & Portfolio Performance
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
Rental Operations Leadership
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
Systems, Process & Scalability
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
Issue Resolution & Service Excellence
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
Business Growth & Market Support
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 entire Seven Keys destinations and services
Leadership & Culture
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
Florida real estate management experience
Prior vacation rental management experience with Streamline software knowledge
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