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NYC has some killer hotel rooftop pools… The James, Hotel Gansevoort and SOHO House to name a few. These places do NOT cater to kids. Mid-May is iffy… but I bet if they are opened they are heated and damn, the veiw would be nice. If you want a Stay-cation, Donovan House on 14th is a good bet as well. I know they open the rooftop in May.