Theres a really nice restaurant in Listowel called Allos. Upstairs there are gorgeous rooms to rent. It's the kind of restaurant where you can have a not too self consciously romantic meal. It's usually quite busy and you can people watch too. It's cosy with a sort of old pub type interior. If you google it you'll get a taste- upstairs is quite glam- four poster beds etc. The restaurant is in the Bridgestown guide etc. The late dinners are not cheap, but theres an early bird option that usually works out quite affordably. The draw back is that you won't get breakfast and there won't be a leisure centre. However you could pop down to the Listowel Arms for breakfast, or to one of the many other places in town open for breakfast.
I like Listowel because there's usually a good few things happening around. For eg St. Johns Theatre usually has something running. There's a cinema. Also John B.Keanes pub is running some comical theatrical evenings over the next few weeks so a really nice place to have a drink and a few laughs. Theres a nice buzz about the town. Don't ask me about night clubs- I know there are a few, but that's all I know. Also if you base yourself in Listowel there's plenty of shopping in the town and its only 20 minutes drive to Tralee which has lots more shops.
Other than that you could easily 'commute' from Tralee or even Killarney. There are loads of nice hotels and restaurants in both.
I'm not sure about NCW, it's out of my territory, but maybe someone else can help.