The Cottages On The Key
January 5, 2023
Siesta Key, Florida
Job Type
$45,000 - $55,000 based on achievement and experience



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 from around the world.

Additionally, vacation rental owners benefit from our full property management services. As a company, we consider each homeowner's individual goals in 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.


As the Guest Experience Advisor, you will be the face and voice of the company and will guide our guests from the pre-booking experience up until their departure. It will be critical to show genuine initiative to learn the industry, grow the company, and make personal connections and touch points with our guests. The knowledge and experience of the homes, the area, and all experiences available will become second nature and be portrayed to everyone you come into contact with. In this position, we’ll rely on you to feed the fire that makes this company run and prioritize keeping “the train” moving at all times.

You will be required to have a passion for Siesta Key and the art of hospitality to proactively learn and gain knowledge of all homes in our portfolio while being socially fluent to our guests for all their needs. This entails responding to leads, sending quotes, utilizing excellent phone skills, responding to in-house guest requests, visiting guests in person and overseeing the in-house guest experience by ensuring all of their requests and needs are properly met by working with our operations department.


  • Respond to all direct and indirect inquiries through OTA’s, incoming calls, emails, and messages.
  • Establish, maintain, and nurture relationships with guests, staff, and vendors.
  • Collaborate with the revenue department to meet Sales Goals for the month.
  • Process and schedule all payments for all bookings in place per agreements / special policies
  • Manage maintenance staff on Breezeway to resolve guest issues and work orders.
  • Become familiar with the inventory of all homes, components, amenities, and experiences we offer in the area.
  • Attend meetings to stay current with procedures and protocols
  • Alert supervisors of any escalated customer concerns
  • Seek out and request 5-star reviews from guests
  • Monitor and respond to guest feedback
  • Other tasks as needed


  • Previous experience in the hospitality industry is required; vacation rental industry experience is preferred.
  • Familiar with using property management software such as Breezeway preferred and a quick learner of technology and apps.
  • Working knowledge of and ability to troubleshoot general residential home maintenance issues.
  • Possess strong customer service abilities.
  • Strong work ethic with the ability to multitask.
  • Ability to work in an ever-changing environment while maintaining a high standard of service.
  • Have knowledge of the Siesta Key area and a quick learner about our properties and what we offer.
  • Enjoy speaking with people with excellent interpersonal, written, and verbal skills.
  • Flexibility to work a varying schedule, including weekends, is required.


Annual Salary: $45,000 - $55,000 based on achievement and experience

Bonus Details:

Bonus based on individual and company performance.


  • 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

Schedule: Must be willing to work flexible hours with the ability to work regularly on weekends.