Most people planning a big family trip to Hawaii start by looking at hotels. For a group of twenty, that’s the wrong end of the problem. The island you choose will shape the week far more than the property will — and the four main islands are genuinely different places, suited to genuinely different families.
Here’s how we think about it, and what we’d ask before recommending one.
Why the island matters more when there are twenty of you
Two people can be happy almost anywhere. A group of twenty has competing needs built into it — a grandparent who’d rather not walk far, a toddler who naps at one, teenagers who want something to do, and at least two adults with very different ideas about what a holiday is for.
What resolves that tension isn’t the hotel. It’s whether the island itself offers enough variety within a short drive, whether there are enough restaurants to absorb a large group, and whether the properties on it are built for families or built for couples.
Get the island right and the property choice becomes easy. Get it wrong and no hotel rescues the week.
Maui — the easiest sell
If not everyone in your group has been to Hawaii, Maui is usually the least controversial answer. It has good beaches, enough restaurants to seat a large party without a two-week-ahead reservation, and resorts genuinely built for families rather than tolerating them.
The island splits into two resort areas, and the choice between them matters. Wailea, on the south shore, is sunnier and more consolidated — several large resorts within walking distance of each other and a shopping village between them. Kāʻanapali and Kapalua, on the west side, are greener, slightly cooler, and have a more relaxed feel.
Properties worth looking at for a group
The Fairmont Kea Lani in Wailea is the one we suggest most often for large families, for an unglamorous reason: the standard room is a one-bedroom suite. That means a separate living area and a sofa bed, which changes what a family of five can do with a single room, and changes how many rooms you need overall.
The Grand Wailea next door goes the other direction — an enormous pool complex with slides, a rope swing and a water elevator. It is not subtle, and if your group includes children under twelve it is very hard to beat.
On the west side, the Hyatt Regency Maui and the Westin Maui in Kāʻanapali both handle groups well and sit on a beach you can walk for a mile. Montage Kapalua Bay is a different proposition again: residential-style units from one to four bedrooms, with kitchens and laundry. For a multigenerational group that wants to eat breakfast together without going anywhere, it solves a problem most resorts don’t.
Visiting Maui now
The 2023 Lahaina fire destroyed most of the town’s historic core and killed more than a hundred people. Three years on, recovery is real but incomplete. The Kāʻanapali and Kapalua resort areas are fully open and operating normally. Front Street partially reopened to vehicles in August 2026, and a handful of restaurants on the north end of town are serving again. The burn zone and much of the historic district remain closed and under active reconstruction.
Maui wants visitors — tourism supports most of the island’s jobs and the recovery depends on it. What the community has asked is that people come thoughtfully: stay out of closed areas, don’t sightsee through neighbourhoods where people are rebuilding, and spend money with local businesses. We’d add one thing for groups specifically. If you’re bringing twenty people, you have real spending power on that island. Use it deliberately.
Conditions change month to month. Maui Recovers is the official source, and worth a look before you travel.
Kauai — for families who want to be together
Kauai is quieter, greener and more dramatic than Maui. It is also smaller, with fewer restaurants and longer distances between them. Whether that’s the appeal or the problem depends entirely on your group.
Our rough test: if your family wants to spend the week largely in each other’s company, Kauai is excellent. If half of them will want to peel off and find their own dinner, it’s harder work than Maui.
The island has two resort areas at opposite ends. Poipu in the south is sunnier and more reliable. The north shore around Princeville and Hanalei is spectacular and considerably wetter — genuinely beautiful, and genuinely rainy in winter.
The Grand Hyatt Kauai in Poipu is the default for large families and deserves to be. It has the pool complex, the space, and enough on-site dining that you aren’t driving for every meal. Koloa Landing, also in Poipu, is worth considering for a different reason — many units have full kitchens and multiple bedrooms, which matters when you’re feeding twenty people.
On the north shore, 1 Hotel Hanalei Bay occupies what may be the best view on the island. Timbers Kauai, near Lihue, offers residential villas and sits closer to the airport, which is a real advantage when your group is landing across a twelve-hour window.
The Big Island — when people want to see things
The Big Island is the one to choose when your group would be bored sitting on a beach for seven days. Volcanoes, black sand, lava fields, snow on Mauna Kea and sun on the Kohala Coast in the same afternoon. It is also the largest island by a wide margin, which means real driving.
That’s the trade. More to see, more time in cars. For a family with teenagers who need occupying, it’s often the right answer. For a family with a toddler and a grandparent with a bad hip, it can be a lot.
Most group lodging sits on the Kohala Coast, north of Kona. The Hilton Waikoloa Village is the outlier worth knowing about: it’s enormous, connected by tram and boat, with a saltwater lagoon and dolphins. It is not a quiet luxury retreat and doesn’t pretend to be. For a group of twenty with children, it’s one of the best value options in Hawaii.
At the other end, Four Seasons Hualalai is among the best resorts in the state and priced accordingly. Mauna Lani, Mauna Kea Beach Hotel, The Westin Hapuna Beach and the Fairmont Orchid all sit between those poles and all handle groups competently.
One more thing in the Big Island’s favour, if it’s relevant to your group: it has the best golf in Hawaii, and several courses within a short drive of the same resorts.
Oahu — underrated for groups
Oahu gets dismissed by people who think of it as Waikiki and traffic. For a large family it deserves a second look, for three practical reasons.
It’s the easiest island to fly into, which matters enormously when your group is arriving from four different cities — more direct flights, more arrival times, fewer interisland connections. It has by far the most rooms and the most restaurants, so a group of twenty is unremarkable rather than a problem. And it’s usually the best value, which matters when the budget spread across a family is wide.
There’s also more to do that isn’t beach-related. Pearl Harbor, the North Shore, hiking, and an actual city — which fills the days that people who don’t want to sunbathe would otherwise struggle with.
Aulani at Ko Olina is the obvious recommendation for a multigenerational group and it earns it — it was designed for exactly that, with programming for children, teenagers and adults running simultaneously. Whether your family wants a Disney resort is a separate question, and one worth asking out loud before you book.
Next door, Four Seasons Oahu at Ko Olina is the grown-up alternative on the same stretch of coast. Turtle Bay on the North Shore is remote and beautiful and suits a group that wants to be away from everything. The Kahala, just past Diamond Head, offers quiet and privacy ten minutes from Waikiki.
A short way to decide
- Not everyone has been to Hawaii, and you want the safest choice — Maui.
- Your family wants to be together, and would rather hike than shop — Kauai.
- People would be restless on a beach; there are teenagers to occupy — the Big Island.
- Arrivals from many cities, a wide budget range, or you want more per dollar — Oahu.
That’s a starting point rather than an answer. The real decision depends on who’s coming, and it’s usually settled in one conversation.
When to book
Hawaii is pleasant year-round, so timing is about crowds and cost rather than weather. Christmas, spring break and midsummer are the expensive weeks and the first to sell out. Late spring and September are the sweet spots — quieter, cheaper, and the water is still warm.
For a group of any size, start nine to fifteen months ahead. Not because it can’t be done later, but because the rooms that let a large family stay near each other go first. Nine rooms booked separately three months out can easily end up scattered across three towers a ten-minute walk apart — which quietly defeats the point of everyone being there.
ʻOhana Getaways plans private group travel — family reunions, milestone trips, company offsites and golf. If you’re weighing up a Hawaii trip for a large group, we’re glad to talk it through. Book a call or read more about how we plan Hawaii for groups.
ʻOhana Getaways LLC is an independent travel advisor of Fora Travel.
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