The Cottages On The Key
May 4, 2023
Siesta Key, Florida
Job Type
$45,000 - $50,000 based on achievement and experience



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 from around the world.

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 uniqueness of their property. 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.


Taking the next step in your career as an Operations Coordinator could be the perfect opportunity for you if you're ready to take meaningful action toward your career goals in the hospitality field.

At The Cottages on The Key, we’re looking for a quick-thinking, proven leader in managing and coordinating all of the tasks associated with keeping our guests happy and coming back year after year.

As our Operations Coordinator, you will be responsible for interacting with our maintenance team, cleaners, and third-party vendors to ensure that our properties are always pristine. We will rely on you to uphold our high standards for quality control, resulting in an unparalleled rental experience for every prospective and incoming guest. If you have a passion for the art of hospitality, work with a high degree of excellence, and can provide outstanding customer service, we want to hear from you!


  • Complete in-the-field training for this role by visiting homes, performing inspections for arrivals, and fulfilling light guest requests for supplies.
  • Create and update all weekly reports and work reports timely and efficient.
  • Schedule any necessary cleanings with designated housekeeping companies for any interim cleaning, deep cleaning, or construction clean.
  • Create and approve weekly payments for all necessary inspections and departure cleaning reports, working cross-departmentally with Accounting.
  • Work with outside vendors to schedule regular/long-term maintenance and guest-initiated requests.
  • Perform property inspections to maintain quality control and inform management of any issues.
  • Assist in project management of long-term projects.
  • Ensure that all issues that arise while guests stay with us are prioritized and handled to their satisfaction.
  • Recommend and discuss compensation with the Guest Experience manager for any issue that arises with guests when necessary.
  • Assist in running Saturday Operations HUB
  • Supervise the  internal insurance claims process which comes from accidental guest damage


  • Previous experience in the hospitality industry is required; vacation rental industry experience is preferred.
  • Familiarity with CRM and property management software such as Breezeway and Streamline is strongly preferred.
  • Proficiency in Google Workspace.
  • Ability to work in an ever-changing environment while maintaining a high standard of service.
  • Have knowledge of the Siesta Key area and be a quick learner about our properties and what we offer.
  • Enjoy speaking with people with excellent interpersonal, written, and verbal skills.

Flexibility to work a varying schedule, including weekends, is required.


Annual Salary: $45,000 - $50,000 based on achievement and experience

Bonus Details: Bonus based on individual and company performance.


  • 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

Schedule: Must be willing to work flexible hours with the ability to work regularly on weekends.