Live In Retreat 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

• 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.