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I've had trouble in the past looking for flights to Cuba since the US seems to restrict sales of flights there.

I'm likely going to Iran later this year, but while flights seem readily accessible, my usual booking sites for accommodation (booking.com, hostelbookers, hostelworld) all don't even have an option for Iran, and refuse to accept Tehran in their search.

Is there an embargo for this or am I just missing something?

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Generally speaking, US businesses are not allowed to do business with/in Iran (there are some exceptions). In practice this means that American accommodation finders can not (or will not) offer accommodation inside Iran as this would run the risk of them breaking US law and getting fined immensely for it. Yes, with the current nuclear deal being a near-reality, this is likely to change soon.

How messed up this is, is shown with that even many businesses that are not American but do business with businesses in America choose not also do business in Iran, as that can result in them being banned from doing business with the US (or be fined accordingly).

Stay on top of things with information directly from the US treasury:

http://www.treasury.gov/resource-center/sanctions/Programs/pages/iran.aspx

An article on what the nuclear deal could result in, business wise:

http://www.theguardian.com/world/2015/apr/02/end-of-iran-sanctions-will-open-gates-to-companies-keen-to-enlarge-markets

A (year old) article on that the US penalises foreign companies and individuals for doing business with/in Iran:

http://www.presstv.com/detail/2014/02/07/349653/us-penalizes-companies-over-iran-trade/

A recent article of the German Commerzbank being fined heavily, in the US, for obfuscating financial transactions with Iranian entities:

http://rt.com/business/240353-commerzbank-billion-fine-sanctions/

The Couchsurfing website has users in Iran.

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This is an Iranian website you can use for booking:

http://en.hotelyar.com/

Even without booking you can find after arriving Iran.

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