I just tried Bing Translate, and even though it nominally supports "Cantonese (Traditional)", their translations don't seem to be much better for the example sentence I gave.

"Please give me his book" is translated to: 請把他的書畀我。 While it does use the usual Cantonese word for "give" (畀), the rest of the sentence still mostly uses Mandarin vocabulary and grammar, notably the 把 construction, the third-person pronoun 他, and the use of the 的 genitive particle, which aren't typically used in spoken Cantonese.

Conversely, 唔該你畀佢本書我 is translated to: "Please give him this book me." This seems to indicate that it doesn't understand Cantonese's ability to use measure words (such as 本) as genitive particles, nor does it understand that the word order of the direct and indirect objects in the sentence are switched compared to the usual order in Standard Written Chinese.