Weather is probably a major factor when you plan your trip to Estero, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 67°F. The rainiest months in Estero are August, July, June, and September, with each month seeing an average of 8 inches of rainfall.