Thanks!! Keep 'em coming!! Forgot to mention we will have a 2 yo with us. Does that change recommendations?
LOL - maybe you need to be near a restaurant the delivers food. And cocktails.
If you happen to have points, I’ve read the Grand Hyatt in Kauai is a good “value” for points. There is a very nice Marriott property (Koloa Landing) near there also. I have enough points to stay several days at the Hyatt, but we like staying at a little condo right next to the water, in a place that doesn’t even have a pool.
We like the south better than the north, but we usually go in February. We stayed in Princeville once in the summer, and it was fine too.
Princeville has towering trees and really makes you feel you’re in Jurassic Park (some scenes were shot there).
Poipu would be a better choice for a family with a kid.
We stayed at the Hyatt when I ran the Kauai marathon. The property is very nice but there is no swimmable beach. Marriott has a sandy beach. There was a Sheraton where we stayed, too, but I think it was converted into private condos.
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Funny you should mention the Marriott properties. I am looking at the Koloa Landing or the Sheraton Kauai 2 br villas. I can only get a garden view villa at the Sheraton. I also looked at the Princeville. Is the princeville oceanfront?
The princeville location has no more villas available. 
Still debating between the 2 options
I believe Princeville is oceanfront but without a swimmable beach.
Poipu can have VERY high waves so please be careful.
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Where are the swimmable beaches?
The tamest beach in the north is anini. No hotels fronting it.
The beach at the Hyatt is lovely but probably not suitable for young children.
I think that with children, you’ll be happier in Poipu, and somewhere with a pool.
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I still have memories of being at a beach in Poipu with a wave that to me was monstrous-several times my height. Even though it was gorgeous, I have great respect for the ocean and its power, so I got out and played in the sand instead. I was 10 or 12 at the time and a decent swimmer.
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I have no idea - sorry.
Be careful when booking if you want “swimmable easy access beachy ocean front.” Some are “ocean front,” but not easy access and not swimmable beach, for example.
I have read that Poipu beaches are better for winter for sure, and we always stay near there when we go in winter.
We stayed in Princeville in the summer, and beaches up there were fine then.
If anyone in your family is interested, kayaking the Napali coast in the summer is way cool. It’s a 17-18 mile kayak along the coast, and pretty spectacular.
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I have a feeling we will be babysitting the 2 yo a lot so mom and dad can explore, so I am leaning towards the autograph collection hotel over the Sheraton. It’s more $ bur the villa is almost twice the size and there are more pools to take the little guy to. Many of the places I looked at didn’t have big enough accommodations.
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The Koloa Landing autograph collection place claims to have the best pool in Hawaii, if that helps 
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It said it had the best pool in the US! Wonder who decided that?
The “villa” at the Sheraton is apparently just 3 hotel rooms connected together.
Definitely check out vrbo as well for bigger units. Hanalei Bay Resort on the north shore, for example, has many privately owned units that could get you the space you need and many hotel type amenities (pools restaurants beach). There are lovely homes for rent near Baby Beach in the south.
It sounds like you’re going about this right – figuring out what you must have, what you really want, etc. If you want the services, you’ll probably want a hotel but if you just need the amenities like pool or beach – and perhaps a kitchen – you are likely to find a better solution with a condo/home.
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I did find a 3 br condo that looks good but it’s non refundable so I need their decision. I offered 3 options.
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If you’re still looking around Kauai, it might be worth your time to consider staying near Kapa’a. It’s east, close to Lihue, and makes access to both northshore and southshore reasonable. It’s less “resorty” but with a small child it may be worth it for convenience to various restaurants, businesses and groceries.
If you are looking for a resort experience there, there is Waipouli Beach resort, which has a beach (though not too popular), a long lazy river pool, and a safeway for supplies right across the street. I believe all units are condo styled so they have a full kitchen. (if you want to find it using google maps, try searching for “Bull Shed, Kapa’a”…(the resort is next door to the Bull Shed restaurant) I’ve had occasional problems in the past finding it with a regular search)
Thanks! For the features we want, we are running up against limited availability or $$$$$$$$$$