I think you answered your own question - there's confusion for the search engine. Similar keywords can do that- even though you say it's clear to you what page is optimized there's some data to prove that the search engines aren't in agreement. (I have a lot of pages and run into the same issue.)
Have you run the competing pages through the Moz optimization tool to see what feedback it gives you? If you see each page is an "A" for the same term, there's some information you can work with to start reworking your content to "un" optimize the pages you don't want to rank.
I like this article Rand wrote that addresses how to correct this issue: http://www.seomoz.org/blog/wrong-page-ranking-in-the-results-6-common-causes-5-solutions