Ask a Jamaican when is the best time to visit the island, and you'll probably get the reply, "Anytime!" It's not far from the truth, as you can have a fun family vacation no matter what time of year you go. Depending on what you plan to do and how much you plan to spend, however, you might find certain times of the year a better fit for your family.

Temperature-wise, it doesn't really matter when you visit Jamaica. On the coast, temperatures generally average between 71 and 88 degrees F year-round, though it can get steamier in the summer months and chillier in the mountainous inland areas of the island. Jamaica has two rainy seasons: one in May and the other in October and November. "Rainy season" does not mean nonstop rain—Jamaica still sees plenty of sun during these months—but your likelihood of having to cancel outdoor activities and spending a few hours trapped indoors with restless kids is higher.

Jamaica is susceptible to tropical storms and hurricanes as well. The Atlantic hurricane season runs from June through late November, peaking from late August to early October. Tropical cyclones don't hit Jamaica every year, and you'll almost always have plenty of warning if one is coming, but a bad storm could disrupt your entire vacation so give extra consideration to travel insurance if you want to travel during peak hurricane season.

Jamaica generally is the most crowded in the winter months as tourists from all over the world seek to escape their chilly homes. Expect the biggest crowds from December through April. If your family travels during the rest of the year, you'll see shorter lines and wait times for activities and dining. However, if your kids like to mingle with other kids their own age—especially if you're planning on staying in a kid-friendly resort or taking a cruise—they might have fewer playmates in the off-season.

If you plan to use your kids' spring break days for your trip, remember that thousands of college students will have the same idea, so you might experience especially large and potentially rowdy crowds of 20-somethings, especially in major beach destinations such as Negril. If this is a concern, ask your hotel when making a reservation whether they also have been booking large college-aged groups during that time.

Unsurprisingly, you'll save money if your family visits Jamaica during the nonpeak months. As flights and hotels will be less crowded, you'll also find better rates, sometimes lower by as much as a third compared to the busy months. Similarly, your tour packages also will come at a discounted rate. The bargain comes with a tradeoff, however. Hotels often trim their staff during off-season, so service levels might drop off. Additionally, hotels often schedule repairs and renovations during the off-season, so check before booking to make sure there will not be disruptive work or closed facilities during your stay.

Most family activities you can enjoy in Jamaica—swimming, snorkeling, boating, rafting, tubing or riding a zipline—will be available whenever you go because of the island's year-round warm weather. Some activities, however, are more seasonal.

If your family enjoys hiking and exploring the mountains, such as the famous Blue Mountains, you might want to avoid the rainy season because your hike could be chilly, wet and muddy. If your family wants to soak up local culture, you also might want to time your visit with the peak season which offer some of Jamaica's annual music festivals. March and April, for example, feature Jamaica's Carnival celebration, known as Bacchanal, during which music, parades and dance shows are plentiful. Kingston also celebrates the indigenous Reggae music for the full month of February, and the annual Jamaica Jazz and Blues Festival, usually in late January or early February, attracts big-name music stars from around the world.