The Cottages On The Key
June 2, 2023
Sarasota, Florida
Job Type
Hourly: $25.00 / hour 



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, Inc., a Siesta Key Vacation Rental Company, seeks to hire an Independent Contractor to serve in a general maintenance capacity. Excellent compensation and weekly stable hours can be provided (part-time to full-time, based on skill level and availability). We service over 70 homes on Siesta Key and the surrounding Sarasota/Manatee areas. Premier home maintenance and superior guest service are what sets us apart from other property management companies!

This position requires a superior background in generalized construction/renovation work and maintenance/repair work, great communication skills, smartphone (texting, calling, use of our app for work orders), organizational skills, people skills, and your own tools. A truck with a bed is required to conduct jobs all over Siesta Key, Lido Key, and Anna Maria Island with parts of Sarasota and Manatee. Light office duty will be required to report for work orders and invoicing. Your day may

include picking up trash from residential homes, replacing light bulbs, light landscaping, or delivering supplies to guests after-hours.


  • Responding to various maintenance work orders to address property owner and guest concerns, such as light plumbing, carpentry, electrical and HVAC repairs.
  • Assisting in scheduling/monitoring larger projects such as deck rebuilds, HVAC installations, backflow tests, and repairs.
  • Working out of our Breezeway App to receive work order assignments and submit invoices for payment.
  • Submit expense receipts on a daily and weekly basis.
  • Communicate thoroughly and practice transparency with in-office personnel, owners, and guests.
  • Be flexible, prompt, and organized.


  • Reliable transportation (truck preferred) and driver's license to transport large items such as bicycles, propane tanks, furniture, ladder, grills, etc.
  • Knowledge in maintenance to include carpentry, electrical, plumbing, heating, and cooling systems, painting, drywall, buffing and waxing, use of power tools, elevators, bicycles, etc.
  • Availability during nights and weekends, including some time on-call as needed.
  • Cell Phone (smartphone) to utilize our work order system.
  • Local distance to Manatee County beaches with commutability to Siesta Key and Sarasota.
  • Thorough communicator and self-starter with the ability to self manage.
  • Listens attentively to questions and comments. Communicates in a professional and composed demeanor under all circumstances.


Hourly: $25.00 / hour

Schedule: Contracted 1099 position with varied hours up to full time, depending on your availability.