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San Antonio generally has a temperate climate which makes it ideal for visitors, except in the summer (including the months of May and September!) when it can get extremely hot and sometimes humid. It's not uncommon for temps to reach 90 degrees and above during the summers, so unless you love to sweat, leave out San Antonio for your summer vacation plans.
The best time to visit is in during the months just before and just after Winter, when rain is less likely and the temperatures are generally mild, closer to 50 degrees (although it still can get colder in the Winter). Fall and Spring are when you're likely to encounter rain, especially in September and May.
You might want to consider April, when the city has it's 2 week long Fiesta (its version of Mardi Gras, or October thru November - the weather is great and the Riverwalk is decked out for Christmas following the day after Thanksgiving.