Property Manager

Company Overview

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)
• 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…