DS is only 14 months right now, but we're tossing around the idea of going back to mexico in april! We went this past year when he was 7 months, and it was perfect! He wasn't really crawling yet so we could still relax and enjoy not having to chase him all around. So im wondering... am i crazy thinking we would have fun this next time around? Or bad idea..... lol 
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I think it'll be a lot of fun! My kids loved the beach/pool at that age
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We just did a mostly all inclusive with our 4.5 yo and our 22 mo. It was great, mostly because I didn't have to cook! We were at the beach and the pool every day and the kids loved it!
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Will you have a separate space for him to sleep, so you can still be awake during nap and after bed time? Like, at least a one bedroom place so you can just sneak in for bed after he is asleep?
If yes, then I think that would be great! We went to Puerto Rico with LO when she was about 20 months and it was really fun. She loved it and it was great seeing her experience new things. But we rented a one bed condo so we could still hang out while she slept. If we were just in one hotel room, not sure if it would have been worth it...
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You'll have a blast! We took our 1.5 year old to Playa Del Carmen last year. All inclusives are great because you don't have to figure out where to eat every meal. There are usually a lot of options for food so it makes it easy. My DD pretty much ate her weight in guacamole and fruit every day. DD also had a great time at the pool and the beach and there were a lot of wild animals (peacocks, iguanas, fish, etc.) wandering around and she adored it. I highly recommend an all-inclusive for traveling with a toddler! You can be as busy or as lazy as you'd like your trip to be!
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We took DS to an all inclusive resort last Christmas when he was 17 months, and will take him again this year when he's 29 months. DS enjoyed the beach/sand and pool. The ocean was too large/turbulent for him so he wasn't a fan. He also didn't mind going site seeing with us!
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