Outside of Wailea Elua condo

Delicious Weekend
Wailea & Kihei with Kids

Friday
Dinner:  Monkeypod Kitchen Wailea
or
Star Noodle Lahaina

Saturday
Breakfast:  Joy's Place Kihei
Coffee:  Andaz Hotel Wailea or Lava Java Kihei
Lunch:  South Maui Fish Company or Coconut's Fish Cafe Kihei
Dinner with the kids:  Ka'ana Kitchen Wailea
Dinner without the kids:  Morimoto Wailea
Dinner or Drinks:  Lobby Lounge, Four Seasons Wailea

Sunday
Brunch:  Nalu's South Shore Grill Kihei

Bonus Recommendations
Home Maid Cafe Kihei
Sugar Beach Bake Shop Kihei
Aloha Wow Wow Kihei
Farmacy Health Bar Wailuku
Ulalani's Shave Ice Kihei

Where to Stay   

 Grand Wailea Hotel Wailea
If children could design a hotel pool area, this is what it would look like.  And make no mistake about it, you stay here for the pools.  Given the inverse relationship between the quality of the food here and the price point, we recommend staying here for only a few days to let the kids get their fill of the 7 water slides, lazy river, rope swing and water elevator.  You can always get a condo or other hotel for the rest of your visit.  That being said, it's hard not to have fun here, at long as you don't go during school breaks, in which case the GW is madness.  Note:  if your kids are under the age of 4, you won't really get your money's worth until they are older.

Vacation Rentals
VRBO
In Maui, VRBO, not airbnb, is king.  VRBO has hundreds of beachfront options in Maui--most are condos.  When traveling with kids, a kitchen and a separate bedroom go a long way to making the adults enjoy the vacation too.  You can choose super-luxury, like Wailea Beach Villas, or beachfront but not as pricey Wailea Elua (pictured), where you can be steps from the ocean.  If your budget is a bit less, in Kihei you can find a wide range of units from $100-400/night.  

Maui Delicious Weekend

Dinner nearby:  Monkeypod Kitchen Wailea

Monkeypod usually has live music and a festive crowd--which means other people can't hear your kids yelling. The half-priced apps during happy hour (when you are often eating with kids anyway) are a great deal.  Our favorite dishes:  raw bar plate, fries, bulgogi tacos. The kids' favorites:  deviled eggs, wings, hummus and veggies and pizzas.  Great service too.  Adult beverages:  The mai tais are famous, but not our thing.  We did love all of Jason's wine recommendations, the beer list, and the less sweet cocktail offerings.  

Dinner not-so-nearby:  Star Noodle Lahaina

This is a long drive with kids, but if you are heading to Lahaina for another purpose, this is a great choice for an early dinner both you and the kids will enjoy.  The food comes out pretty fast as well, which is nice with children in tow. Everything here seems to be delicious, and the price point is well below most Maui restaurants.  Super friendly, helpful service. The kids seemed to love the same dishes we did: pork buns, hot and sour bowl, garlic noodles, and of course, the malasadas! For the adults: Spicy jalapeno margarita is well balanced. Great beer and sake list. Skip the wine.

Breakfast:  Joy's Place Kihei

Most mornings it may just be easiest to eat toast or cereal in your condo. But other days it is fun to head into Kihei and start the day off with a healthy acai bowl or a light breakfast sandwich. Kids will love taking the food to go and eating on the rocks on the beach across the street.  There are lots of other options people love (Kihei Caffe for example), but do your kids really like to wait 30 min in line to eat?

Coffee:  Mokapu Market, Andaz Hotel Wailea or Lava Java Kihei

For regular brewed coffee, your hotel or condo is the move. And can't highly recommend anywhere for espresso.  Java Lava at least has excellent customer service - super friendly people and fairly quick service most days (the frozen mocha thing is delicious, though not for purists). 
If staying in Wailea, the best option is the Mokapu Market at the Andaz in Wailea. On weekends, it serves delicious brioche donuts from Donut Dynamite, which will delight your children as well. Espresso is just so-so, but you can drink it while staring at a killer view.

Lunch:  South Maui Fish Company Kihei

This little red trailer churns out absolutely amazing fish.  We heard lots about the poke, but despite 3 tries, we never got there before they ran out. Get there by noon and you should be ok. However, have a backup plan: if South Maui Fish Co. does not get spectacular fish, they close completely. Our kids loved the ahi tacos, as well as the super friendly owner. So did we. We will continue to stalk this place on future Maui visits.

Lunch: Coconut's Fish Cafe Kihei

Far from the tourist trap it may look like, this place will please both adults and children. The coconut shrimp is tasty, albeit sweet. Kids will love it as-is, while adults may prefer it with some hot sauce instead of the sauce provided. The poke bowl is awesome-the brown rice is the perfect texture-and the fish tacos are legit, particularly with some added Cholula. Order at the counter and take a seat at one of the surfboard tables.  

Dinner without the kids:  Morimoto Wailea

Normally we avoid outposts of mainland restaurants, but Morimoto is just plain delicious. The view is also spectacular. Pricey, but so is everything in Wailea, and these prices are well below places like Ko and Spago if you order strategically. Cocktails are tasty, though many tend to be pretty sweet like most places in Maui. Wine list is solid and not as overpriced as others. Favorite dishes:  whitefish carpaccio, hamachi tacos, watermelon gazpacho, calamari salad, and crispy whole fish. Skip the shrimp tempura - a bit too heavy. Click to book.

Dinner with the kids:  Ka'ana Kitchen Wailea

Ka'ana takes the farm to table approach to another level with central focus on locally sourced ingredients.  Kids will love the beverage options and the keiki (kids') menu. Some of the dishes trend a little sweet, but there are plenty of others to choose if that is not your thing. The octopus and abalone risotto are stand-outs, as are the desserts. The view is slightly obstructed by the bar below, but still pretty darn nice.  The cocktails are nice too.  The wine is insanely overpriced, but the selection is good.  Our favorite thing about Ka'ana is the friendly, helpful service, which is particularly important when dining with kids.  Click to book 

Drinks:  Lobby Lounge, Four Seasons Wailea

Skip the overpriced luau with its watered-down drinks & underwhelming food and come to the Four Seasons instead.  Hawaiian entertainment begins at 5:30 PM (live music and dancers), which will captivate your children while you enjoy their complimentary bar snacks and tasty cocktails (Thai-garita was our favorite).  If you are hungry, the hand-cut fries and fresh sashimi are delicious.  Children can eat an entire tasty meal including dessert for $10.  The service was the best we had anywhere in Maui. 

Brunch:  Nalu's South Shore Grill Kihei

If your kids are like 99% of children, they are all about sweet breakfasts. Nalu's will deliver on that front and then some. The infused water station is also really fun.  The breakfast dishes are huge, so one will be plenty for two to share. There are also some healthier options for the adults. You will be in the same parking lot at Home Maid Cafe, so save room for malasadas if you can. And whatever you do, do NOT order espresso at Nalu's. That mistake must not be made by anyone else.

Bonus Recommendations

Malasadas:  Home Maid Cafe Kihei

Hit this strip mall hole-in-the-wall for made-to-order malasadas you don't have to wake up at 6 am to enjoy.  Eat within a few minutes.  Both sugar and cream-filled are to die for. 

Pie:  Sugar Beach Bake Shop Kihei

We never got here in time to try the malasadas (they often run out by 7:00 am), but who cares when the key lime pie is this good?  Get one.

Smoothies & lemonades:  Aloha Wow Wow Kihei

The lemonades and limeades are delicious -- Limonada de coco was our favorite.  Really liked the acai bowls too.  Lots of delicious smoothie options as well.

Healthy stuff:  Farmacy Health Bar Wailuku

Total find for fantastic juices and smoothies.  Not terribly out of the way if you hit after landing in OGG on your way to Kihei or Wailea.  Very good acai bowls.  Farmacy will put a smile on your kids' faces too.

Shave Ice:  Ulalani's Kihei

For once, the tourists are right.  So don't bother trying the others - Ulalani's is the best.  Some flavors are far better than others.  Our favorites were mango, coconut and calamansi (local citrus), whereas the kids liked pineapple and mango best.  The micro is plenty large enough.  Shave ice is super sweet, so we skipped the toppers and ice cream underneath, but if you have a real sweet tooth or are ok with your kids in a sugar coma, try those out.  They have a bunch of locations.