The Cottages On The Key
February 16, 2023
Siesta Key Beach, Florida
Job Type
$50,000 -$60,000



The Cottages on The Key is a vacation rental property management company based in Siesta Key, Florida. With a commitment to the art of hospitality, we are passionate about sharing experiences in the area with guests worldwide.

Additionally, vacation rental owners benefit from our full property management services. As a company, we consider each homeowner's individual goals, creating customized white glove services that match their financial goals and the property's uniqueness. It's that same individualized approach that has made us successful and has contributed to our growth.

At The Cottages on The Key, culture is essential. We strive to create a supportive and inclusive environment where everyone feels valued. When working with us, you’ll find that our team functions as a unified and collaborative unit, which enables us to maintain an excellent work-life balance.


The Owner Experience Coordinator is responsible for the day-to-day management of all property owner accounts, along with the assistance of onboarding new ones. At The Cottages on The Key, the owner experience sets us apart from other short-term rental management companies. The relationships we foster with our owners are key to maintaining our brand standard. This position will require proactively seeking solutions to issues/triage problems before they occur. The Owner Experience Coordinator will want to optimize the company's best practices and improve any pain points of our owners’ experiences.

This position will report to Mathew Farhat, Head of Business Development while supporting cross-departmentally as administrative and operational needs arise.

Day-to-day responsibilities will include but are not limited to: responding to emails, making phone calls to maintain relationships, visiting in-house owners, and auditing expense reports for property owners every month.

While this job is not 24/7 on call, there is an after-hours timeliness that is expected, which may result in the ability to have a more flexible schedule.


  • Managing and becoming familiar with the current portfolio of owners.
  • Advocating for all property owners’ needs.
  • Creating and maintaining relationships with property-owning individuals in our portfolio.
  • Assistance with new client onboarding and following through on all aspects of the onboarding process while utilizing
  • Note all relevant information and ensure cross-departmental communication when necessary for new clients.
  • Practicing follow-through and communicating with appropriate parties on any and all agreements made with new homeowners.
  • Facilitate communication and retrieval of paperwork from owners.
  • Responding to owner inquiries regarding maintenance on the home.
  • Willingness to be available for owner contact.
  • Management of gift basket to owner program and delivering gift baskets to in-house owners.
  • Reviewal of owners’ monthly P&L statements.
  • Respond to expense inquiries following month-end statement processing.
  • Create and upkeep owner hotlist of action items, preferences, dislikes, etc.
  • Focused on retaining business partnerships.
  • Scheduling meetings with current owners as the need arises.
  • Development of relationships with a focus on building trust and ensuring all owners' needs are met.


  • Previous experience in CRM and account management.
  • Familiar with using Gsuite.
  • Possess strong customer service abilities.
  • Strong work ethic, with the ability to multitask
  • Ability to work in an ever-changing environment while maintaining a high standard of service.
  • Have knowledge of the Siesta Key area and quick learner about our properties and what we offer.
  • Enjoy speaking with people with excellent interpersonal, written, and verbal skills.


Annual Salary: $50,000 -$60,000

Benefits & Perks: 

  • Paid time off, such as PTO, sick days, and vacation days
  • Health insurance
  • Employee recognition programs
  • Relocation assistance
  • Workplace perks such as recreation activities, food and coffee, and flexible work schedules