The Cottages On The Key
September 4, 2023
Siesta Key, 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.


We are excited to offer a $1,000 Sign on bonus! 

$200 paid after 30 days of employment, $200 paid after 60 days, and $600 after 90 days!

The Cottages on the Key, Inc., a Siesta Key Vacation Rental Company, seeks to hire a Maintenance Technician to serve in a general residential maintenance capacity. We service over 70 homes on Siesta Key and the surrounding Sarasota/Manatee areas. Premier home maintenance and superior guest service set us apart from other property management
The ideal candidate will have experience in general residential maintenance with a confident skillset to complete minor home repairs. 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.

We offer excellent compensation, and regular weekly hours (part-time to full-time, based on skill level and availability) can be provided. This role is a 1099 position.


  • Completing preventative maintenance checks and work orders to address property owner and guest concerns, such as unclogging garbage disposals if necessary, changing lightbulbs, resetting cable boxes, etc.
  • 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- a  truck is required, and a driver's license to transport large items such as bicycles, propane tanks, furniture, ladder, grills, etc.
  • Knowledge of and ability to perform general maintenance is required.
  • Flexibility to work scheduled shifts during evenings and weekends, including some rotating on-call shifts as needed.
  • Cell Phone (smartphone) to utilize our work order system.
  • 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.