Vacation Rentals Jobs in Florida (NOW HIRING)

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

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

Proactivity

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

Schedule

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