Host OS: Mac OS 10.11.1 Guest OS: Ubuntu Trusty 64 Virtualbox: 4.3.30 Vagrant: 1.7.4 Example with trace thrown: vagrant@vagrant-ubuntu-trusty-64:/vagrant$ cat tt.py import tempfile with tempfile.TemporaryFile(dir="/vagrant") as tf: tf.write("testing testing testing\n".encode('utf-8')) vagrant@vagrant-ubuntu-trusty-64:/vagrant$ python3.5 tt.py Traceback (most recent call last): File "tt.py", line 4, in <module> with tempfile.TemporaryFile(dir="/vagrant") as tf: File "/usr/lib/python3.5/tempfile.py", line 753, in TemporaryFile newline=newline, encoding=encoding) FileNotFoundError: [Errno 2] No such file or directory I think the underlying system call that's causing the error (I attached the full strace in case that's helpful): open("/vagrant", O_RDWR|O_EXCL|O_DIRECTORY|O_NOFOLLOW|O_CLOEXEC|0x400000) = -1 EOPNOTSUPP (Operation not supported) Finally, the mount point looks like this: vagrant on /vagrant type vboxsf (uid=1000,gid=1000,rw)