As with all Caribbean islands, the Caymans have high and low seasons. Hurricane season starts around June 1 and goes until November 30. Prime time for visiting is mid-December until mid-April. But great hotel deals can be found in late April and May while the weather is still beautiful and the beaches are less crowded. Just bear in mind, some restaurants aren’t open during low season and some hotels have fewer amenities. If you plan to travel during a prime winter holiday such as Christmas, New Year's, or Presidents' Day weekend, book well in advance to ensure vacancy as well as car rental.