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Cheapest AI Deals for couple in 20s

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Hi!

I've been doing some research into AIs in the Caribbean but have found it a bit overwhelming and difficult to navigate. I hope some of you will be able to help guide me a bit.

I'm looking for something around $100 pp, per night for 7 nights + airfare. I've only been able to find a couple resorts that fit this (Iberostar? Riu?). But these look just like standard prices. Where can I find deals? Either for these resorts or for pricier ones but after discount will fall into the budget. I'm not sure when to look for deals either. Tentatively aiming for May 2015, should I book now or wait for deals to roll around?

Some information on preferences that might be helpful, in order of importance:
1. Clean, relatively modern (not super old)
2. Amazing beach
3. Acceptable food and drink (AI)

Other preferences:
No need for lots of excursions or other things to do.
No need for super active night life or even young crowds

Thank you for the help!!

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