The months from November to mid-December are the best time for visiting Montego Bay Jamaica. The temperatures range from mid 70s F to the high 80s F throughout the year. The weather is also the most pleasant during these months making the city exploration a fascinating experience. It’s also easy to book cheap flights to Montego Bay as well as affordable hotels during this time. Avoid visiting Montego Bay in July as it is the hottest month with an average temperature of 83 F. The rainy season is from May to June and September to October, though you will experience brief afternoon showers only followed by sunshine.