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 Property Manager to join our Key West team.
This role sits at the center of the homeowner and guest experience; owning relationships, coordinating operations, and ensuring every property performs at a high level.
You’ll act as the primary point of contact for homeowners, proactively managing expectations, resolving issues, and driving satisfaction, while collaborating cross-functionally with maintenance, housekeeping, and reservations teams.
The right candidate is proactive, highly organized, and relationship-driven, capable of balancing multiple priorities while maintaining a high standard of service.
Serve as the dedicated point of contact for homeowners
Build trust through consistent, proactive communication
Understand and manage homeowner expectations, including revenue goals
Address concerns quickly and professionally
Develop and implement strategies to optimize property performance
Coordinate with maintenance, housekeeping, and internal teams
Ensure homes meet operational, safety, and quality standards
Maintain detailed knowledge of each property (systems, compliance, upkeep)
Resolve guest and homeowner issues before escalation
Ensure a seamless experience from check-in to check-out
Collaborate across departments to deliver consistent service
Support onboarding of new homeowners (data entry, scheduling photography, setup)
Assist with transition and integration of new properties
Contribute to business development efforts when needed
Maintain accurate documentation, reports, and system updates
Track property performance and create action plans
Utilize company systems to streamline communication and operations
Act as a brand ambassador for Seven Keys Vacations
Maintain strong local market knowledge and share insights with owners and guests
High School Diploma or equivalent
Active Florida real estate brokers license (preferred but not required)
1+ years minimum experience in Vacation Rentals / Short Term Rentals
Experience with property management software required; Streamline preferred
Prior experience in customer service with demonstrated desire to delight the clientele
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
$60,000 - $85,000
Annual bonus opportunity includes personal and company-wide goals
Paid time off, such as PTO, sick days, and vacation days
Health, Dental, and Vision insurance
Car allowance
Act as dedicated point of contact for homeowners by completing the following duties which include but are not limited to:
Assist with developing strategies to implement within the management contract, which will achieve the desired competitive edge.
Proactively understand homeowner expectations, including revenue targets, and consistently communicate and monitor satisfaction;
Communicate in a timely manner;
Answer questions and address client relations matters or concerns; and
Develop and maintain quality relationships.
Assist with onboarding new homeowners for property management services, including verifying required information is entered accurately into the system, scheduling photography, etc.
Collaborate and follow up with Maintenance, Housekeeping or other department heads regarding services needed in each property.
Assist and manage reservation and customer service team duties
Work to resolve issues that have the potential to escalate and work collaboratively to take the proper steps to guarantee guest and homeowner satisfaction.
Act as a brand ambassador, promoting all Seven Keys destinations and services to guests and colleagues alike.
Provide a high level of dedicated customer service, regularly interacting and communicating with current homeowners to keep them informed while sustaining and cultivating the relationship.
Obtain and maintain detailed knowledge of the local area passing this information onto the sales team, homeowners and guests as appropriate.
Work directly with the homeowners to ensure they are comfortable with the maintenance and care of the home.
Gain full knowledge of and maintain all operational systems and services in rental properties as required, including but not limited to code compliance, utility supply, general maintenance, etc.
Maintain updated reports and ensure all information is documented and filed appropriately as well as damage reports collation from housekeepers and inspectors.
Create action plans for homes.
Utilize company software as directed to capture information, communicate effectively with others, and streamline processes.
Set an example of professionalism by work ethic, appearance, teamwork, preparedness, and every other facet to build trust, confidence, and respect from all those you work with.
Contribute to business development efforts as needed and work closely with internal teams to facilitate seamless transition and onboarding of newly assigned properties and homeowners.
High School Diploma or equivalent
Active Florida real estate brokers license (preferred but not required)
Prior experience in customer service with demonstrated desire to delight the clientele
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