Caribbean or Key West Anyone?

Hi! I am a seasonal employee currently in Denali, Ak. I was wondering if anyone could give me some advice for finding a job in either Key West or the Caribbean. I have wanted to work there my whole life, and am not sure where I should start. Cool Works helped me find this job in Alaska this summer, and I would like to go somewhere warm, near the water for winter. Any advice would be helpful!!! Thank you so much