Best Winter Sun Destinations for Families

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There’s nothing quite like escaping a gray, cold January with your family and landing somewhere warm and beautiful — and when it comes to winter sun destinations for families, Hawaii sits at the absolute top of the list. The islands offer something for every type of family, from luxury resort experiences on Maui to the vibrant energy of Honolulu’s Waikiki strip. Here are four exceptional properties to consider for your winter Hawaii trip.

How to Choose the Right Hawaii Resort for Winter

• Choose your island intentionally. Oahu (Honolulu/Waikiki) is the most vibrant and accessible; Maui tends to be a bit more resort-focused and relaxed; the Big Island and Kauai offer more nature and adventure.
• Look at the trade wind patterns. Most of Hawaii’s beach resorts are positioned to take advantage of trade winds — but the leeward (west) side of most islands tends to have calmer water and more consistent sun.
• Consider the flight. Hawaii is a long haul from most of the continental US — factor in flight time and layover options when choosing your island, as some are easier to reach than others.
• Check what’s included. Many Hawaii resorts charge resort fees that cover parking, Wi-Fi, and beach equipment — factor these in when comparing properties.
• Book early for winter. December through March is peak season in Hawaii — popular resorts fill months in advance and prices climb. Early booking gets you better rates and more room choices.

Our Top 4 Winter Sun Family Resorts in Hawaii

The Kahala Hotel & Resort, Honolulu

The Kahala is one of Honolulu’s most storied luxury properties, tucked away in the quiet Kahala neighborhood just east of Diamond Head. It’s a world away from the bustle of Waikiki while still being very close to the city’s attractions, and the resort’s lagoon — which is home to a dolphin program — makes it immediately magical for kids. This is a property for families who want genuine luxury in a serene, private-feeling setting without completely disconnecting from Oahu’s offerings.

Fairmont Kea Lani Maui

The Fairmont Kea Lani is one of Maui’s most beloved luxury resorts — a gleaming white Moorish-inspired property on the golden sands of Polo Beach in Wailea. It’s an all-suite property, which is a genuine gift for traveling families: more space, more storage, and more ability to maintain some semblance of a bedtime routine. The resort has multiple pools, direct beach access, and the kind of polished, attentive service that makes you feel genuinely looked after. For a splurge family trip, this is hard to beat.

OUTRIGGER Kaanapali Beach Resort, Maui

Kaanapali Beach is consistently ranked among the most beautiful beaches in the United States, and the OUTRIGGER property sits right on it. The OUTRIGGER brand has deep Hawaiian roots and a genuine connection to the aloha spirit — it’s a resort that feels like it belongs in Hawaii rather than just being placed there. The beachfront location, pools, and activity programming make it a fantastic family choice on Maui’s energetic west side.

Ka La’i Waikiki Beach, LXR Hotels & Resorts

LXR is Hilton’s ultra-luxury collection, and Ka La’i brings that level of refinement to Waikiki’s legendary beachfront. For families who want to be right in the heart of Honolulu’s most iconic neighborhood with access to world-class dining, shopping, and beach life — while staying somewhere genuinely exceptional — this is a compelling choice. Waikiki in winter is particularly lovely: warm enough for the beach, cooled by trade winds, and full of the energy that makes Honolulu so addictive.

Tips for a Hawaii Winter Family Trip

Book activities in advance. Popular experiences like snorkel tours, luaus, and helicopter flights book out weeks ahead in peak season — don’t leave these for when you arrive. Pack reef-safe sunscreen only. Hawaii law requires reef-safe sunscreen, and it’s genuinely the right thing to do when your kids are swimming in some of the most biodiverse waters on earth. Embrace the time change gradually. Hawaii is 5-6 hours behind the East Coast — kids often wake early for the first few days, which actually works beautifully for catching golden-hour beaches before the crowds arrive. Try at least one locally-owned restaurant. Hawaii has an incredible food culture that goes far beyond resort dining — plate lunches, poke bowls, and shave ice from local spots are as much a part of the Hawaii experience as the beaches.

Final Thoughts

Hawaii in winter is a dream — there’s really no other way to put it. Trading snow boots for flip-flops, trading gray skies for that particular Hawaiian blue, and watching your kids’ faces when they first see those beaches makes every mile of the flight worth it. Check availability for your dates at any of these four wonderful properties and start planning the trip your family will be talking about for years.