The Cottages On The Key
January 18, 2023
Siesta Key, Florida
Job Type



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 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 extremely important. 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.


Do you love working in hospitality and providing excellent customer service?

If so, this opportunity to live and work alongside our team in Siesta Key, Florida, might be exactly what you’re looking for.

Currently, we’re looking for the right person to be our Operations Field Runner. To succeed in this role, it’ll be important for you to be an excellent team player with the awareness to pitch in as needed to maintain our brand's high standards.

Your day-to-day will include opening and closing our office and stocking the front lobby with snacks. Besides assisting with various project-based tasks, you will also help our Operations Manager with administrative duties such as assigning work orders, ordering supplies, coordinating deliveries, and visiting properties to check

what needs to be replenished. It will also be essential for you to work well with our maintenance team.

If you’re naturally self-motivated, flexible, with a positive attitude, and have availability on Saturdays and Sundays, we’d love for you to reach out.


  • Unpacking supplies for arrival inspections.
  • Monitoring the field operation of laundry service each week.
  • Performing arrival inspections on a weekly basis, with an emphasis on Saturdays and Sundays.
  • Managing the inventory garage by ordering, accepting, and coordinating supplies.
  • Work orders, processing damage waiver items, and other administrative tasks.
  • Delivering various supplies throughout the island as needed per guest or maintenance requests.
  • Entering the field to check on properties for any specifics required in the home.
  • Aid supervisors with detail and information needed for long-term work orders.


  • 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 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.


Salary: $40,000


  • 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