The plan is to rendezvous with my parents in Hawaii this July. This is the only time I can go as HK teachers don't have much in the way of vacation time, so this is non-negotiable.
I will be traveling along with DD, as DH can't get off of work. That's a whole other issue, but anyway. She will be 8 months.
We intend to look for a condo/apartment with three bedrooms. It will be my parents, my adult sister, and DD and I.
We are looking for a place relatively close to the beach, with access to a pool, as well. Things like hiking and parasailing are not necessary. Proximity to restaurants and shops is a plus. We could rent a car and are open to visiting attractions like a pineapple plantation, museums, etc.
Any insight into what would be a good fit for a baby and grandparents scenario?
Personally, I really like Kauai or Maui; BUT if you want to be close to restaurants & shopping than I actually think Oahu may be best for you. You could visit Pearl Harbour, there is lots of shopping, restaurants, etc.
Kauai is much less populated, less dining options, and most of the activities are outdoors type stuff. I LOVE IT but I'm not sure it would be the right fit in your scenario?
I second Oahu, especially if you want any sort of museums or history. I think it's great for multi-generation trips because there will be something for everyone. Waikiki would be your best bet for easily walkable restaurants and shopping. If that's not appealing and everyone can walk a little farther, the Gold Coast is a great way to be close to Waikiki but in a much quieter area. Check out the Diamond Head Beach Hotel (it's condos) or other properties around it for that.
Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one's lifetime. Mark Twain
I've been to Maui and Kauai and love them both for different reasons. In your case, I'd recommend Maui, specifically the Kaanapali area. Front Street has great shopping and restaurants, Kaanapali beach has good snorkeling and swimming, lots to do in the area. Popular hotels around there are the Hyatt, Westin, Sheraton. If you drive a little further out there's a Ritz Carlton. You could also do a condo like Honua Kai or the Westin Villas. That might be helpful with your DD - washer/dryer and a fridge.
Reading fail - you said you wanted a condo. I still think Honua Kai or Westin Villas might be good options!
I would do Maui. We rented a condo in Wailea right on the beach with a pool on property. The beach is beautiful, and we were an easy drive to several restaurants, grocery stores, and other shops.
Maui for sure. My family (parents, sis, husband) rented a condo just south (I think) of Lahaina and loved the location, as well as diverse activity options around the island.
Sounds like condo in Maui in the Kaanapali area would be perfect for you.
I agree with this. I'd recommend looking into timeshares in addition to condos. One that we like is marriott ocean club. We also like Westin but it's a longer walk to the main area of shops and restaurants in kaanapali