Reservation and Housekeeping Specialist at Cottages to Castles of Sanibel & Captiva

Boutique Vacation Rental Agency Now Hiring Full-time Reservation and Housekeeping Specialist

If you think you have what it takes to help island visitors experience the vacation of a lifetime, please reply with your contact information and resume with job history and qualifying skills/experience.

What We Are Looking For:

We are looking for a full-time Reservation/Guest Experience Specialist, with an emphasis on coordinating housekeeping and maintenance schedules.

The office is open 8:30 am - 5 pm, 6 days a week. Schedule flexibility is a must, due to schedules being based around arrival days, seasonal holidays and peak season occupancy. Must be able to work Saturdays.

As a vacation agency, we will be the busiest when most folks are taking vacations - ie: weekends, holidays, spring break, summer, etc. We’ll need you to be available. You may be called upon after normal business hours and on weekends, and flexibility is key. You are the boots on the ground when our guests or owners need assistance.

Our top priority is to offer clients near and far a pleasant, easy and informative experience before, during and after they have booked their vacation - as well as providing exceptional service during their stay.

The Skills You'll Need:

  • You need to be a self starter and self motivated. We want our guests to be impressed.
  • Being computer savvy in a Mac environment is a plus. We use proprietary software to manage all aspects of our business.  
  • You are a Problem Solver. We always seek to head problems off at the pass, but they do arise. When something doesn't go according to plan, you will need to go into action and work to turn problems into opportunities, whether it is assisting a guest with internet access or getting creative when there is a power outage. 
  • You can follow established business processes, are detail-oriented, punctual and are organized. You can handle multi-tasking and finish what you start.
  • You're cool under pressure, especially if there is a weather event looming or you're addressing an issue with an unhappy guest. It happens!
  • You like to smile, and are genuinely interested in people and being an Ambassador for us, and the island. 

What You'll Do:

You will be responsible for coordinating front desk duties with weekly housekeeping schedules and act as a front line contact for all guests and vendors. The ability to multi-task is important. You may handle guest inquiries, organize reservations, work orders, third party vendors, guest's special requests or problem solve, while providing top notch service at all times. You will complete other duties as assigned, such as inspecting a property for arrival, or arranging and scheduling work orders for service. 

Exceptional customer service and accuracy are essential to creating a memorable vacation experience for our island visitors. 

  • Maintain a friendly, cheerful demeanor at all times, while providing personalized service. Smile!
  • Greet arriving guests, facilitate guest departures, report and/or coordinate any housekeeping or maintenance issues.
  • Accept incoming calls, answer email inquiries, and be able to accept reservations in person and over the phone, using our reservation software.
  • Follow established procedures and processes
  • Maintain and process daily reports.
  • Maintain good guest relations by keeping abreast of property amenities and island events in order to answer questions and concerns with timely and knowledgeable responses in person and on the phone.
  • Coordinate deliveries, mail for guests, as well as troubleshoot basic television and wifi connectivity issues (will train).

You may be asked to assist with social media posts, blogging and website updates pertaining to your department.

Wish List:

  • Flexible, go with the flow of the day, while remaining organized and on-task
  • Detail-oriented, able to follow established processes and finish assigned tasks accurately, and in a timely manner.
  • Able to work in what can sometimes be a fast-paced environment and multi-task
  • Quick learner and self-starter

*Must be able to work Saturdays, holidays and after hours on-call, when necessary

*Prior vacation rental, guest service/hospitality experience, preferable.
*Valid driver's license and reliable transportation required.
*Familiarity with Sanibel and Captiva is a must.


  • Tolls paid.
  • Regular bonus opportunities based on performance.
  • Sponsored Professional Development Courses, Education Opportunities


  1. We offer a competitive compensation package, HSA health insurance, generous paid vacation and paid tolls.
  2. On-Call/After Hours compensation available.

We look forward to meeting you!

Vaccinated candidates strongly considered. We continue to observe safe social distancing when meeting clients and working with vendors. Sanitary cleaning protocols are observed in our public spaces.

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