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Many people find that the best time of year to visit the Cayman Islands is during the winter months, and hotel room rates certaintly reflect that. Rates from Dec 15th through April 15th are much higher than the rest of the year. During the winter, temperatures are consistent around 75-85 degrees farenheit, with humidity at a comfortable level.
The switch from "dry" to "rainy" season tend to happen around mid to late May, at which point things tend to get hotter and more humid right through late October when the seasons switch around again.
As all Caribbean afficianados know, June 1st to November 1st is Hurricane Season, so one should watch out for weather systems and take out travel insurance with some of the savings from the low summer hotel rates.
The slowest time of year is September, but this is also a time to get great rates, and for divers the visibility is normally the best of the whole year.
Winter visitors are mostly from the Northern and Eastern states of the USA, whereas in summer those from the South and South West find the Cayman temperatures (high 80s to low 90s) relatively enjoyable.