There are a number of different cultivars / species of pineapples, and some of them are more cold hardy than others. A hard freeze will cause heavy damage to the leaves of all types I've tried outdoors, but some can survive until temps drop into the low 20F range IF they're well established in the ground with all other needs being met.

I'm in zone 8a, and some of the hardware chains here are selling like 3 different types of "hardy pineapples" that are listed on the tag as being cold hardy to zone 8b. I don't believe that's accurate though.

The thing is, if you have freezes but still generally never get colder than upper 20F range, they might only ever be ornamental and not produce fruit. The freeze will generally knock back the main plant, forcing it to come back from pups each year.

Funny thing is that some parts of Florida are legit considered tropical. You could always bring them inside during the colder months.