The Cottages on the Key
April 24, 2023
Siesta Key, Florida
Job Type
$80,000 - $100,000



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 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.


The Cottages on the Key is looking to hire a Controller who seeks the opportunity to help build and scale a department and grow with our company for many years. This opportunity is for an individual who seeks to work in a fast-paced, dynamic work environment and directly with our Executive Team.

Your experience, ability to provide oversight to multiple components of our company, and leadership are all key factors in your success. In this role, you will oversee all the financial matters of our company, including accounting, analyzing financial data, and making strategic suggestions to our leadership team that will allow for long-term health and success.

We are looking for a self-motivated individual with excellent communication skills. You must have a firm understanding of accounting operations and financial analysis with the ability to delegate appropriately when necessary. Having experience in the vacation rental industry is a must.


  • Maintains the books and ensures that all company transactions and assets are properly recorded.
  • Planning, directing, and coordinating all operational accounting functions.
  • Responsible for tax planning and compliance with all Federal, State, and local corporate and other applicable taxes.
  • Oversee risk management and insurance functions.
  • Cash management and treasury functions.
  • Responsible for a roll-up of accounting budgets, forecasts, and actual results compared to the budget every month.
  • Prepare and submit all applicable reports to Owners and Executive Team.
  • Work with our team to draft our EOY P&L and property management tax documentation.
  • Work with our team to ensure we are on track for monthly P&Ls for owners and the company.
  • Streamline processes to help reduce back-office financial operations.
  • Identify and work with Owner Experience Team to select recommended actions to improve property performance and reduce recurring expenses to owners.


  • Must have vacation rental accounting experience and knowledge.
  • Experience with vacation rental trust accounting is highly desired.
  • Knowledge of Streamline property management software is a huge plus.
  • Ability to process complex data and make thoughtful decisions.
  • Exceptional project management / organizational skills.
  • Ability to work in a small team and carry out initiatives with little supervision.
  • BA in accounting; CPA or MBA in finance desired.
  • Certifications such as CPA, CFA, and CMA are preferred.


Annual Salary: $80,000 - $100,000


  • 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