Will AirDrop work between an OS X virtual machine and an iPhone? I'm looking for an easy way to transfer files to my iPhone and I don't have a Mac.

I was going to use VirtualBox or VMware Workstation Player.
Is your question here really "How do I get files from a Windows computer onto an iPhone", and you're using an OSX VM to enable AirDrop to achieve that?

If so, you can look at several other ways of sharing files:


DropBox
iCloud for Windows


And most of the big file-sharing services have iPhone apps that will allow you to upload from the desktop side (OSX, Windows, Linux, etc), and access them on the phone.