The aim of this paper is to examine several problems with translation and how these can be addressed. This paper discusses a number of stylistic factors that contribute to translation problems. Some of them are due to cultural differences, while others relate to the different lexical and grammatical forms of the source language (SL) and the target language (TL). Finding the proper equivalents to some collocations and the use of loan words in the source text may pose problems during the translation process. It is not always easy nor possible to find a word with the same meaning in the TL, because some words possess cultural meanings. It is noteworthy to mention that existing idiomatic expressions in the SL may create more problems for translation. This paper highlights the challenges that a translator may face and how those challenges can be surmounted. The main objective of this study, however, is to examine the problems that arise when translating culture-bound idioms and expressions from Arabic into English and vice versa. The strategies that a translator can employ to overcome these obstacles are proposed and discussed. Moreover, the differences between the Arabic and English languages, in addition to their cultural differences, make the process of translating a veritable challenge.