Maui with a Toddler: Practical Tips for a Smooth Family Trip

We took way too many photos during our six-night stay in Maui, so we went through them and pared things down. Still, it ended up as two posts because we like to share everything. In this post we cover:

  • where we stayed
  • where we ate
  • our neighborhood
  • how we saved money

In the next post we’ll share:

  • the activities and adventures we did (with a toddler)
  • a home-related purchase we made to remember the trip
  • the vacation tradition we continued in Hawaii

We also wrote about flying with a toddler and adjusting to time change over on Young House Life.

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Where we stayed: we found a two-bedroom condo at the Aina Nalu resort in Lahaina through HomeAway. Booking directly with the owner via HomeAway saved us a significant amount compared with booking through the resort or an agent. For a two-bedroom, two-bath unit with a full kitchen, washer and dryer, and kid-friendly extras, the rate was an excellent deal compared to local hotel prices back home. The condo was within walking distance of beaches, shops, and restaurants — the location couldn’t have been better.

The owners made the condo very kid-friendly: they provided a pack ’n play, stroller, plenty of beach toys, outlet covers, and cabinet latches. We researched the area ahead of time and relied on high reviews on HomeAway before booking, and the stay lived up to expectations. Below is the Aina Nalu lobby.

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We chose a two-bedroom unit so our toddler, Clara, could sleep in her own room. The main bedroom and en-suite were comfortable and convenient for our family’s needs.

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Many resort guests stayed in hotel-style rooms with housekeeping, but our unit was a private residence with a regular key and no daily housekeeping. We appreciated feeling like it was our own condo for the week. Having a washer and dryer in the unit was especially handy — we did a load mid-trip to freshen up Clara’s sand-and-ice-cream-covered clothes.

Here’s Clara near our door so you can see the layout with pathways connecting the buildings and common areas.

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The resort had pathways to the lobby and two pools. Some days the pool area was busy, and other days we had it to ourselves.

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There were plenty of loungers for sunning and shaded cabanas that felt like king-sized beds near the pool — perfect for naps or reading with a view.

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More snapshots of the grounds and pool area — the second pool is visible in one of these photos, and you can see how the rooms look back toward the common spaces.

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This is a sweet photo of Clara. Each of us picked one souvenir: John got a blue HI shirt, I bought a soft Maui tee, and Clara got pink Crocs she calls her “rocks.” They were perfect for sand and surf.

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Lahaina is a charming, walkable area on Maui’s west coast with plenty of shops and restaurants within easy reach of the resort.

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Several nearby beaches were within walking distance. One we loved was “Baby Beach,” where a coral reef blocks the waves and creates a calm, shallow area that’s ideal for young kids. There are some rocky spots, but staying close to the shore keeps things safe and fun.

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Clara spent hours playing where the water met the sand, splashing waist-deep, and pouring buckets of water over her head — always counting to three before she did it.

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We slathered on SPF and mostly relaxed — phones off, minimal blog checking, and no makeup for the week. Pure vacation mode.

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When it got hot we cooled off in the water and kept an eye beyond the reef for whales. We saw plenty from other beaches (more on that in the next post).

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The sandbar at one beach stretched far out with only waist-deep water, and the view back to Lahaina and the neighboring islands was spectacular.

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Clara’s favorite moment might have been watching a kayak go by with a little girl and a dog. She shouted a delighted string of greetings as it passed — pure toddler joy.

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She also loved covering herself in wet sand. Yes, she really did that.

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Now for the food. We ate incredibly well — a colorful variety of local dishes and treats kept us satisfied. In one collage: fried rice breakfast from Lahaina Coolers, Loco Moco from Aloha Mixed Plate, burgers from Cool Cat Cafe (often rated the best burger on Maui), and a gigantic slice of Hula Pie from Kimo’s.

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Lahaina Pizza Company had great pizza and an upstairs balcony with ocean views and passing cruise ships. We also had a funny hibachi moment where the fire show terrified Clara; she screamed “fire is hot!” and we ended up taking the meal back to our cabana to eat. It was chaotic but memorable.

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Clara enjoyed many local favorites — snow cones, ice cream, bagels, and fries — and we kept snacks like crackers, fruit, and veggies on hand for when she wasn’t interested in restaurant dishes. At one restaurant she proudly sounded out the “Aloha” sign and a server rewarded her with a flower.

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We also spotted whales while eating at Aloha Mixed Plate — one spectacular breach right offshore. Whale watching is thrilling each time; every sighting feels like the first.

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Other places we enjoyed (no photos) include:

  • Take Home Maui (deli with fresh pineapple)
  • Sunrise Cafe (affordable local breakfast spot)
  • Bradda Hutts (outstanding BBQ near Hana)
  • Auntie Sandy’s (banana bread at Ke’anae Peninsula)
  • Sure Thing Burgers (local organic burger stand in Lahaina)
  • Moose McGillycuddy’s (sports-bar-style place)
  • Cheeseburger in Paradise (waterfront location, not connected to the Jimmy Buffett chain)
  • Fred’s (great Mexican in Kihei)

And John insists on recommending Ululani’s shave ice: their texture is incredibly fine — almost like snow — and they’ll add more syrup if yours tastes too icy. It’s the best shave ice we had on the trip.

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How we saved money:

  • We’d saved for years since our last big trip, so we had a travel fund to draw from.
  • We learned flight prices can be lower mid-week and often spike on weekends; booking about 2.5–3 months ahead seemed to work for airfare to Hawaii.
  • We used HomeAway to find a two-bedroom condo with a kitchen and laundry for a reasonable nightly rate, which saved on dining and baggage fees.
  • We carried on luggage and packed light, relying on the condo’s washer and dryer.
  • We bought groceries for basics like cereal and snacks and cooked simple meals in the condo to balance restaurant costs.
  • We split many restaurant entrees and sometimes took leftovers for the next day to stretch meals further.
  • We booked excursions online or through discount booths at the resort to get better rates on whale watching and other activities.

That wraps up Part 1 of our Maui trip: accommodations, neighborhood beaches, and food. Part 2 will detail our activities and excursions, the keepsake we bought, and the vacation tradition we continued in Hawaii. If you have favorite restaurants, activities, or tips for Maui, please share — we’d love this to be a helpful resource for others planning a trip.