I've seen in these documents about Bitbucket Server that it offers the option of squashing commits when pull requests are being merged:
However, it doesn't appear to be enabled in the Bitbucket Server available at bitbucket.org (I believe this is known as "Bitbucket Cloud"). At least, it's not available in the repositories I've been using. Does the feature need to be enabled in my repositories or is it just not available on bitbucket.org?
It's not currently available, but we're currently working on it. Check this page for more updates - it was just updated today! https://bitbucket.org/site/master/issues/8995/provide-the-option-to-use-git-merge-squash
Alistair's answer is spot on, but to address a related part of your question, Bitbucket Cloud and Bitbucket Server are separate offerings. While they share the same core value proposition at a high level, we use different technologies optimised for each platform and prioritise features to solve problems that affect users of each platform in different ways. One nice side effect of this is that it lets us experiment quickly in Cloud, and focus on challenges specific to a self-hosted setup in Server.
We try to take the best features in each offering and make them available in the other when it makes sense, but at any given time the two won't be the same.
It's confusing to see some version of Bitbucket documentation say the feature is available, but then I can't find it on bitbucket.org.
I guess Atlassian renamed Stash to Bitbucket Server to bring the similar products closer together. However, in a case like this, it would have been better for the products to have kept different names. They should have just added "Powered by Stash" messages to the bitbucket.org website.
Oh, well. At least the merge-and-squash feature will be available on bitbucket.org soon.
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