Festive Season at Grand Wailea: One Week, Eight Waterslides, Zero Holiday Stress

Making new dolphin friends at golden hour—the Grand Wailea’s iconic fountain is even more magical in holiday light.

Let me just start with the pools, because that’s where we spent 80 percent of this trip. Grand Wailea doesn’t have “a pool.” It has a water park disguised as a luxury resort feature. Rope swing. Water elevator. Deep pool for scuba instruction. Waterslides in every direction. Swim-up bar. Our kids were blissfully entertained for hours, and we rotated between a lounge chair, a paperback, and the occasional iced coffee like seasoned pros.

You haven’t truly earned your mai tai until your child has rope-swung into the pool at least 37 times. Yes, there’s a line. Yes, it’s worth it.

One of many laps on the legendary waterslide circuit—also known as the kid cardio loop. Hours of entertainment, zero need to “go explore” anything.

The beach, though, might’ve been our favorite spot of all. Wailea Beach is about as good as it gets in Hawaii: wide, swimmable, gently active, and always just a few sandy steps away. We watched sunsets here every evening, usually barefoot, sometimes with shaved ice, once with a half-eaten poke bowl we refused to give up. It’s the kind of place that doesn’t need filters—just maybe a wide-brim hat.

Our kids had a hard time choosing their favorite pool. Solution? Ride a dolphin into the actual ocean. (Inflatable, yes. But the feeling was real.)

Wailea Beach isn’t just beautiful — it’s swimmable. Calm mornings, soft sand, and just enough wave action for boogie boarding without the ER visit

Holiday-wise, the resort manages to feel festive without getting in your face about it. Palm trees wrapped in lights, menorah lighting at dusk, and a North Pole mailbox tucked beside the koi ponds that actually got our kids to sit still and write something longer than “I want an iPad.” Santa even shows up via an outrigger canoe, which frankly sets a new bar for entrance drama.

The magic of Christmas hits differently when you’re barefoot and holding a shaved ice. Santa delivers to Maui too—we triple-checked.

O Tannenbaum, but make it Maui. The Grand Wailea lobby’s towering surfboard tree is both festive and highly Instagrammable.

Our room had everything we needed and nothing we didn’t: a soaking tub I never wanted to leave, a lanai made for early morning coffee, and beds we still talk about like exes we’re not quite over. If you want a little extra calm, the Napua Tower upgrade is worth it—private check-in, snacks that accidentally turn into meals, and a place to escape when your crew wants to “just do one more waterslide."

As for the food, we were pleasantly surprised (and that’s saying something). Humble Market Kitchin had one of the best dinners we’ve had on Maui—fresh island flavors, panoramic views, and that golden hour light that makes you feel like you’re in a travel ad. During the day, Bistro Molokini served up fast, flavorful lunches that didn’t cost us our cabana spot. And the Market Cafe deserves a shoutout for somehow always having exactly what we needed (read: caffeine, and backup sunscreen).

This trip gave us the exact holiday we needed: festive, relaxed, a little sandy, and surprisingly magical. No matching pajamas required.

Even the grass is photo-worthy here. Evening strolls along the cliffs became our new favorite tradition — no shoes, no stress.

• Book early. This place fills up fast for the holidays—and the good rooms and poolside spots go first.

• Cabanas are worth it, especially if your idea of parenting involves sitting near your children while reading in peace.

• Wailea Beach is the one. Calm surf, soft sand, and just enough action for kids without becoming chaos.

• Don’t skip the spa—the hydrotherapy circuit is a little slice of actual peace.

• Holiday programming hits that perfect middle ground: festive, but not cloying.

• Napua Tower is a quiet flex that also includes snacks, so win-win.

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