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So many ways to "just let go"
Make a big splash
Find your own special place
Discover something new
It's all here
Two Great Resorts.
Many experiences.

Island Grand Outpost

Careers at TradeWinds Island Resorts


Search and Apply for Jobs


At TradeWinds Island Resorts, Hospitality Professionals will find a truly one of a kind employment experience.

As the largest beach resort employer in the area, we offer lots of opportunity for advancement and growth. We currently have over 250 different job titles, from Boat Captain to Vacation Planner Professional and Resident Artist to Adventure Center Supervisor. Many positions offer stepped rate scales so we can get our best employees more money faster. Every position offers some form of bonus, commission, or other incentive programs for doing a great job. Cross training is extremely common at TradeWinds. Learn different jobs to get more hours and more experience!

Check out some of what we have to offer!

  • Our Rewards and Recognition Committee meets monthly to recognize Employees for Guest Service, Teamwork, Outstanding Professional Achievement and to award our Employees & Managers of the Month.
  • A Company picnic and Holiday Party are open to all employees.
  • Thanksgiving Turkeys are distributed each year.  Big Ones!
  • Our TROP point program gives employees their choice of prizes after earning points for a job well done.
  • Appreciation for being accident free comes in the form of breakfasts, lunches, and TROP points.
  • Birthdays and Company Anniversaries are celebrated every single day.
  • Our Annual Awards Ceremony is a HUGE deal!  Thousands of dollars in door prizes alone in addition to Service, Safety and Employee/Manager of the Year honors.
  • Friends and Family Guest Room rates at great prices!
  • Medical, Dental and Optional Life Insurance is available to eligible Employees.
  • Supplemental Accident, Disability and Cancer policies are also available.
  • A 401(k) with Company match is available to eligible Employees.
  • Our E-Flash daily newsletter keeps everyone up to date on the latest news.
  • Local discounts just for being an Employee of TradeWinds!
  • Annual Opinion Survey for Employees to rate their Manager and the Company as a whole.
  • A Company softball team, tennis program, poker games, putt-putt golf tournaments, volleyball games, basketball team, running club and so much more…
  • Employee Partner Tax Filing Assistance

Our Employees, though, are truly what makes our Company special. Our Guests have a consistent expectation of us to be “aggressively friendly”, and we have the same expectation of each other. See what it means to be a Hospitality Professional at TradeWinds Island Resorts!


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TradeWinds Guy Harvey Outpost | TradeWinds Island Grand | St. Pete Beach, FL 33706
| | © 2015 TradeWinds Island Resort

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