Details verified October 22, 2026.

Hawaii is the single most requested family destination in the points world, and for good reason. The flights are long enough that lie-flat seats matter, the hotels are expensive enough that points save thousands, and every island offers something different for kids. Here is how a family does Hawaii on points, from picking an island to booking the flights and hotels.

Picking the right island for your family

Oahu is the best island for first timers. Waikiki has the densest cluster of points hotels in Hawaii, the beaches are calm for small kids, and day trips like Pearl Harbor and the North Shore are easy. If your family has never been to Hawaii, start here.

Maui is the resort island. The beaches are the best in the state for families, the resort pools are built for kids who never want to leave, and the Road to Hana makes a great day trip with older children. It is also the most expensive island, which is exactly why points matter most here.

The Big Island is for adventurous families. Volcanoes National Park, manta ray night snorkeling, and black sand beaches give teens and tweens stories their friends do not have. The island is huge, so rent a car.

Kauai is the quiet one. Lush, dramatic, and slower paced. Best for families who want nature over nightlife, though the points hotel options are thinner than Oahu or Maui.

Getting there on points

From the mainland US, Hawaii runs about 20,000 to 40,000 miles each way in economy depending on the program and season. Alaska Airlines miles are a sweet spot for West Coast departures, and American and United both fly nonstop from Dallas to Honolulu and Maui.

Southwest is the sleeper pick for families. It flies to Hawaii from several West Coast cities and, crucially, flies between islands for as little as 5,000 Rapid Rewards points. If you want to split a trip between Oahu and Maui, Southwest’s island hops are the cheapest way to do it. A Southwest Companion Pass covers the second traveler on every one of those flights.

Book early. Hawaii award seats in school break periods disappear six to nine months out, and summer seats go fast too.

Where to stay on points

Hyatt has the strongest Hawaii footprint for families. The Andaz Maui at Wailea is the aspirational pick, a Category 8 property that runs 35,000 to 45,000 points per night depending on peak pricing. The Hyatt Regency Maui is the more practical family choice with a great pool complex and penguins on site. On Oahu, the Hyatt Regency Waikiki Beach puts you across the street from the sand.

Hilton counters with the Hilton Hawaiian Village on Oahu, a sprawling beachfront complex that kids love, and the Grand Wailea on Maui, one of the most famous resort pools in the world. Hilton’s fifth night free on award stays (Silver status and up) cuts a five night stay by 20 percent.

Marriott has the Royal Hawaiian and Moana Surfrider on Waikiki Beach plus the Waikoloa Beach resort on the Big Island. Marriott also offers a fifth night free on award stays, which stacks nicely on a week long trip.

Things to do with kids in Hawaii

Snorkel Hanauma Bay (Oahu). A protected bay with calm, shallow water and reef fish right off the sand. It is the easiest first snorkel for kids, and the beach itself is gentle enough for younger ones to play while older kids explore.

Take a surf lesson at Waikiki (Oahu). The waves at Waikiki are small and rolling, and local instructors teach kids on longboards every day. Even first timers usually stand up on their first lesson, which makes it a core memory kind of morning.

Drive the Road to Hana (Maui). Waterfalls, bamboo forests, and the black sand beach at Waianapanapa State Park along one winding coastal road. It is a full day and best with older kids who enjoy the drive itself, but the stops are the Hawaii your kids will describe to their friends.

Explore Hawaii Volcanoes National Park (Big Island). Steam vents, craters, and lava fields you can walk right up to. Start at the visitor center, then take the short crater rim trails. It is the rare national park that feels like another planet to a kid.

See Waimea Canyon (Kauai). Called the Grand Canyon of the Pacific, with red rock walls and waterfalls you can see from easy lookout stops. No long hike required, which makes it a great payoff for families with small kids.

When to go

The sweet spot for families is late April through May and September through early November. The weather is excellent, the crowds thin out, and award availability opens up. Mid December through early January and spring break are the hardest times to find award seats and the most expensive for the nights you cannot cover with points.

The bottom line

A family of four can fly to Hawaii and stay five nights at a beachfront resort almost entirely on points. The playbook is simple: pick your island based on your kids’ ages, book flights the day schedules open, and stack a fifth night free benefit on the hotel stay. Start planning nine months before school breaks and Hawaii stops being the trip you cannot afford.