If your machine isn't accessible to the service you are using, then your only option would really be to build a local implementation of the service that will exercise your API. A rake task that sends the POST with the file and the info would be a nice thing so you could start your rails app locally, and then kick off the task with some params to run your application through its paces.
This is the case any time you are trying to develop a system that can't connect to a required resource during development. You need to build a development harness of sorts so that you can exercise all the different types of actions the external service will call on your application.
This certainly won't be easy or straight forward, especially if your interface to this external service is complicated. Be sure to have your test cases send bad POSTs to your application so that you are sure you handle both what you expect, and what you don't.
Also make sure that you do some integration testing with the actual service before you "go-live" with the application. Hopefully you can deploy to an external server that the web service will be able to access in order to test. Amazon's EC2 hosting environment would let you set up a server very quickly, run your tests, and then shut down without much cost at all.