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What is the difference between 詰まらない and 詰らない? Are they both valid words? Are they pronounced the same and do they have the same meaning?

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The first one is つまらない, the second one is なじらない. They have different meanings. – Zhen Lin Jul 14 '12 at 13:20
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You should not use 詰（なじ）らない without ふりがな. Otherwise, almost all people will read it as つまらない. – Gradius Jul 14 '12 at 15:24
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That's certainly what I assumed at first, until I checked the dictionary... – Zhen Lin Jul 14 '12 at 18:32

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What is the difference between 詰まらない and 詰らない?

As the comment indicates, it is possible that the first is tumaranai while the second is naziranai, the negative of the verb nazir-. While this is technically possible, it is not so simple. First, the kanzi for nazir- is not so common and few people will be able to read it. Second, tumaranai may be written as either 詰まらない or 詰らない. (For the rest of this response, I will be ignoring the nazir- reading.)

To expand on the second point, this is a matter of okurigana (送り仮名). There are a number of similar words in which there are multiple spellings: okonau (行なう, 行う), kotowaru (断わる, 断る), arawareru (現われる, 現れる) etc. This is documented by the Agency of Cultural Affairs here. This is a stylistic difference.

Are they both valid words?

Yes.

Are they pronounced the same and do they have the same meaning?

Yes.

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つまらない is not written as 詰らない. The rules with order of priority are (1) The first mora belongs to the kanji part, (2) Any mora that overlaps with an affix belongs to the okurigana. Here, the notion affix is taken in a wide sense that includes even the final i or e of the stem of a vowel ending verb or any derivational affixes. つまらない is tum-ar-anai, and まらない is the okurogana. The allowance exception (許容) allows an extra mora to belong to the okurigana, but does not lessen the okurigana. – sawa Jul 14 '12 at 22:23
@sawa You are mistaken. Link: 大辞泉: 詰（ま）らない (dic.yahoo.co.jp/…) Notice the （ま） portion, which is indicating the okurigana may or may not include the -ma-. – Dono Jul 14 '12 at 23:24
Sorry about it. Looks like it had been used. But it is not in accordance with the rules given by the government that you linked. – sawa Jul 14 '12 at 23:54
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@sawa I think the main issue here is how one parses the word. You indicated that it is tum-ar-anai. However, as the negative of tumar-, lets consider the more basic verb. True, there is a verb tum- from I assume tumar- derives from. However, the verb conjugates as follows: tumaranai, tumarimasu, tumareba. The constant portion is tuma(r), and it is this portion that is taken by some to be the stem leaving -r(u/anai) for the okurigana. On the other hand, for people who parse it as tum-ar- as you indicated, only the tu would be the stem leaving -mar(r/anai) for the okurigana. Hence, two spellings – Dono Jul 15 '12 at 0:18
送り仮名 rules are not strict. The Japanese government is recommending a set of "proper" rules for modern writing. But there are many historical and private texts not following the rules. Even modern authors may break the rules on purpose. If you write a document, it will be safe to use 詰まらない as つまらない. However, if you read someone's document especially before the WWII, you should not stick to the rules. – Gradius Jul 15 '12 at 17:56

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