Places to stay?

I'm looking for places to stay for two trips over the coming months.

a) A cute rental house/condo in Kauai. Ideally on the North Eastern part of the island. Hot tub or large bath tub would be nice. Something close to the action. Hopefully in view of or on the beach. 3 nights.

b) A cute boutique hotel in NYC/Manhattan. It doesn't have to be super fancy and I don't expect a big massive room or anything, but it should also be close to some action. 2-3 nights.

Thoughts and recommendations?