Does SKYPE phone work in Japan?

HI! I am going to Japan for 2 week in October and would like to know if I used my Apple Mac with wifi and a Skype telephone number will I be able to talk to my friends and family in America for free still? Or do I have to rent a mobile phone when I am there?

It most certainly does. And most hotels have an internet connection in your room to use your own laptop. Not sure that a SKYPE handset would work as Japan has a totally different sytem.

My friend who resides in Okinawa has a Skype Phone for his computer, but I am unsure how it works.

It's possible to use skype on your computer but the mobile skype phone is unavailable in Japan as yet. check out http://www.skype.com/intl/en/allfeatures/3skypephone/