iTrip Vacations Annapolis
July 25, 2022
Annapolis, Maryland
Job Type
Hourly: $25.00



iTrip Vacations was started in 2008 by vacation rental owners for vacation rental owners. The company has since become one of North America's top property management leaders. Each iTrip Vacation destination is managed by a local team, available 24/7, who lives in the area. This, combined with state-of-the-art systems and proven processes, enables iTrip Vacations to provide boutique-level services backed by a national brand to all our short-term rental owners and guests.

Our beautiful city of Annapolis is home to incredible museums, historical attractions, the U.S. Naval Academy, and gorgeous ocean views. No wonder people come from all over the United States and the globe to vacation in this fascinating city.

As a team, we are committed to offering our guests incredible experiences and cultivating a work culture where our employees thrive. 


If you love history and hospitality and you’re known for being concise, precise, and decisive when it comes to quality and maintaining high standards, then you might be the ideal person to fill the critical role of Quality Inspector here at iTrip Annapolis.

The person who will thrive as our Quality Inspector in Annapolis must be a fantastic team player, thorough in everything they do, and have a knack for working quickly through a list with an eagle eye for anything that may be broken, out of place, or empty. As our Quality Inspector, you will have the vital task of ensuring that each individual STR unit on the iTrip platform is guest-ready before guests arrive. This includes but is not limited to cleanliness, the property's functionality, and maintaining inventory for things like furniture, electronics, and consumables.

This is a contract 1099 position. Weekends are a must in hospitality, so please only apply if you can work Saturdays and Sundays.


  • Ensure the property is impeccable and ready to provide world-class accommodation for every guest.
  • Driving to units to solve problems, provide assistance, or deliver additional material or supplies.
  • Confirm trash has been taken to the curb on respective trash days and cans are emptied/returned to the house before the next guest check-in
  • Interact directly with cleaning companies and service contractors.
  • After a guest has checked out, be the first person on the property to assess any damage, check for lost and found items, prepare for cleaning teams, and/or other tasks as necessary.
  • Light maintenance repairs such as changing light bulbs, replacing batteries in locks, changing propane tanks, cleaning grills, etc.
  • Monitor our reservation calendar to effectively schedule cleanings, maintenance, and inspection dates.
  • Maintain storage unit, transport linens from local laundromats, and run miscellaneous errands as needed.


  • Extremely task-oriented with high standards for quality and accuracy.
  • Experience with housekeeping is a plus.
  • Technical expertise with basic knowledge of home repairs and home systems such as heating, cooling, and electrical.
  • Proficient with tools such as a drill, hammer, screwdrivers, etc.
  • Proficient in using web-based apps and computers.
  • Comfortable filling out reports and working with third-party vendors.
  • Able to perform physical labor as needed.
  • Valid Driver’s License with a clean record.
  • Access to reliable transportation.
  • Flexibility to work on weekends is required.


Hourly: $25.00

Schedule: Local travel throughout Annapolis and the surrounding area is required to be onsite and inspect each STR. You will be required to work regular business hours with flexibility for evenings, weekends, and holidays as needed up to 20 hours per week.