Employment Opportunities at Winter Park Lodging Company

Winter Park Lodging Company’s success is built entirely on the quality and effort of our team members.  We consider each team member to be an ambassador of our brand and we strive to create a fun, friendly, and energetic work environment that fosters our mission, vision and values.  The postings below are positions currently available within the company, but we are always seeking out good candidates.  If you are interested in joining our team, we encourage you to send us a resume and a note about you by emailing jobs@winterparklodgingcompany.com.

Owner Relations Team Member

Type: Year-round, Full-time, Hourly

Reporting: Owner Relations Team Manager

Job Summary: This position will work closely with the Owner Relations Team Manager in handling all aspects of the department.  The main objective of this department is to foster long-term relationships and build trust with all of our owners.  For that reason we’re looking to add team members who would like to grow with the team and help build those relationships.


  • Proactive written and verbal communication with owners
  • Development of owner newsletters, surveys, and other online tools to communicate and evaluate company’s performance for owners
  • Handle day to day requests and questions from homeowners
  • Assist with monthly owner statements including proof reading and adding and editing charges to owners
  • Regular monitoring of property revenue performance and analyzing why properties are not performing to expectations
  • Visit properties to evaluate upkeep/decor and work with owners to coordinate updating of any furnishings or inventory needed in the properties
  • Meet with owners face to face as needed
  • Weekly check of owner arrivals to confirm owner inspection list with Head of Housekeeping/Inspections
  • Work alongside the Property Care Teams to ensure owner requests are met as well as to communicate property issues to the owner, as well as coordinate with outside vendors working on properties.
  • Assist in the on/offboarding of properties.  This includes the behind the scenes tasks of setting up the properties in all software systems, helping to coordinate photos/floor plans, confirming that maintenance, housekeeping and marketing related needs are taken care of prior to properties going live online, and other tasks that might arise.  This also includes all communication with the property owners to answer any questions and help guide them through the process of coming on program and educate them on the ins/outs of renting short-term. Off boarding includes managing 30 day blocks, shutting off integrations at the appropriate times and removing WPLC items from the properties.
  • Perform related duties in the homeowner department as assigned by Owner Relations Manager



  • Excellent verbal and written communication skills
  • Detail oriented, good analytical and organizational skills
  • Excellent computer proficiency (MS Office – Word, Excel and Outlook)
  • Ability to perform multiple tasks at once and work in fast paced/deadline driven environment
  • Ability to work independently and to carry out assignments to completion within parameters of instructions given, prescribed routines, and standard accepted practices
  • Ability to lift 75+ lbs
  • Ability to solve practical problems and deal with a variety of concrete variables in situations where only limited standardization exists. Ability to interpret a variety of instructions furnished in written, oral, diagram, or schedule form.  Ability to be fully accountable for decisions is a must
  • Clean, professional appearance
  • Must have reliable transportation and a valid driver’s license
  • High school diploma

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Maintenance Technician

Type: Year-round, Full-time, Hourly

Reporting: Maintenance Manager

Job Summary: We consider the members of our Maintenance Department to be the face of our company.  With no physical check-in process for our guests, often times the only person-to-person interactions we have with them is when they’re in need of help. The ideal candidate for this position is someone with an equally strong background in both customer service and maintenance related work. The daily work in this department requires the ability to self-schedule as well as re-prioritize tasks as required by our guests.


  • Complete maintenance tasks entered into the system in a timely manner and with sufficient detail so that the Guest Experience Team can follow up with all guests and so that Accounting has the information needed to properly invoice each task.
  • Respond to all guest requests including but not limited to: maintenance issues, delivery of supplies from office, requests that need to be purchased and delivered to guests.
  • Assist with completing inspections for guest or owner arrivals as needed.
  • Report all cleaning and maintenance related issues to the housekeeping manager and housekeeping personnel.
  • Perform annual maintenance inspections of all properties.
  • Assisting in all duties as assigned.


  • The ability to multi-task and communicate well with other employees is a must for this position.
  • Proficient use of Microsoft Office (Excel & Word) and ability to quickly learn/adapt to other software applications
  • Clean, professional appearance
  • Ability to lift 75+ pounds
  • Detail oriented
  • Ability to speak English fluently- Spanish is a plus
  • Must have reliable transportation and a valid driver’s license.
  • High School diploma.

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