WhereToStay.com, Inc.
April 8, 2022
Anywhere, Texas
Job Type
Competitive Salary with bonuses based on company performance



Caribbean Villa Rental Agent

Step into a career with the company that revolutionized the travel industry

Position: Full-Time

Location: Remote


“WhereToStay.com has been listed in National Geographic Traveler's "5 Best Travel Websites" and Forbes' "Best of the Web.”

WhereToStay.com began in 1995 as a hotel travel guide with one mission -  to help travelers find the perfect vacation property for their Caribbean getaway. “Luxury Villas,” our division dedicated to offering the world’s finest portfolio of Caribbean villas, set sail under WhereToStay.com in 2001. We were the first travel website to feature traveler reviews, redefining the industry by giving travelers a voice. Our innovative spirit and dedication to our guests are deeply engrained values long-held by our company and each team member. Because of this, our shopper-approved ratings continue to rank us as a 5-star company, creating return guests year after year.  


As a WhereToStay Caribbean Rental Agent, you should possess a desire to help guests plan their dream Caribbean vacation. Your passion for luxury properties and curating incredible vacations should be evident in how you warmly and courteously handle villa leads. Your destination expertise in the Caribbean will be a significant help in listening to clients as they express what kind of vacation they are hoping for so that you can recommend the ideal location, properties, and activities custom-tailored just for them. 

As our villa experts and concierge team lend a personal touch to vacation planning, you will work alongside them to handle every detail so clients can focus solely on enjoying the Caribbean!  Your success in this role will be shown by how many strong “rental agent/client relationships” you build and the strong rapport that leads them to continue to book with you in the future. As a Rental Agent, you will find this position deeply rewarding if you are an outgoing, detail-oriented, and highly motivated individual.


  • Expertly recommend locations, properties, and activities to the customer after actively listening to their vacation desires.
  • Work with property managers to check availability, process, release holds, and invoice the client once a booking has been confirmed.
  • Educate and inform customers of their villa reservation terms and conditions, and encourage them to get travel insurance to protect their investment. 
  • Thoroughly complete paperwork and administrative processes with high attention to detail.
  • Attend the WhereToStay team weekly meetings with a positive attitude and an eagerness to improve continually. 


  • 2+ years in hospitality or luxury travel experience. Caribbean Villa rental sales experience is strongly preferred.
  • Demonstrated ability to interact successfully with affluent clientele
  • Strong destination-based knowledge of the Caribbean
  • Highly motivated to sell; ability to build strong customer relationships and offer exceptional service
  • Strong written and verbal communication skills for telephone and email contact
  • Self-disciplined and accountable in achieving goals, learning, and improving wherever possible
  • As a remote villa specialist, you must have a designated space for a home office, free of distractions, with high-speed internet.
  • Must be able to work a flexible, full-time schedule during regular business hours.
  • Proven ability to work well with others as well as on your own.


Annual Salary: Competitive Salary and bonuses based on company performance


  • Health Insurance

Apply now if you are knowledgeable about the Caribbean, a skilled salesperson with a passion for travel, and want to further your career in a proven and innovative company we’d love to hear from you. Knowledge of Caribbean Villas is a plus!