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So you cannot “upload” books to cloud per se, but you can “Send to Kindle” them (this is exactly what Calibre does by “sending to cloud”).
You need to go to your Amazon account from PC, go to Your Devices and Contents, and find there what is your Kindle-associated e-mail. There is also something like “a list of trusted e-mail addresses”, add your e-mail address which you going to send files from.
Then, you can send to this e-mail some formats like mobi, doc, pdf, and some others (I don’t remember) and they will appear on all your devices with the same Kindle account. However, IIRC all of them will have a label of “Personal Document”.
Regarding azw3, yes you cannot send them, unfortunately. It is related to ASIN number (a very long story), so in short try to convert them to .mobi files in Calibre. .mobi files are larger in size than azw3, because usually a .mobi files contains two formats: mobi7 and kf8 (which is azw3).
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