I probably would not have received those days off.
I may not have received those days off.
I wish I went to Okinawa in Spring because it was raining when I went. I did not request days off in Spring, however, because I just started working with my company around that time.
ご質問の文章を全て訳すと、このような感じになります。英語圏の会社ですと、休暇が”取れない”ということはなく休暇は”申請する”か”申請しない”かで決まりますので、上記の例文ではrequest days offを使っています。
この場合、次のような言い方ができますよ。
ーI went to Okinawa during the rainy season, so it rained a lot. I should have gone in the spring, but I had just changed jobs, so I might not have gotten the time off work.
「梅雨に沖縄に行ったので雨ばかりだった。春に行けばよかったが、転職をしたばかりだったので、休暇を取れなかったかもしれない」
I had just changed jobs.「私は転職したばかりでした」
I might not have gotten the time off work.「仕事で休暇を取れなかったかもしれない」
ご参考まで！
日本 
カナダ 
