Where to Stay in Oahu
Waikiki
Waikiki is crowded and touristy, but for good reason. This is where you stay if you want the most options for food, activities, shopping, and nightlife, all in one place.
It's a great home base. 95% of Oahu's hotels are here. Plus Airbnbs are allowed to rent by the night (unlike other areas in Oahu where they require a 30 day minimum).
There are so many options for good food (from economical Musubi Cafe to big time splurge Sushi Sho).
Waikiki is very walkable, but there are plenty of transportation options if you want to explore nearby Honolulu neighborhoods.
There's tons to do in Waikiki (beaches, surf lessons, catamaran tours, shopping, and nearby hikes like Diamond Head or Manoa Falls), but it's also easy enough to drive out to North Shore or Kailua for the day.
The ocean stays pretty calm on the south side of the island, even during the winter.
And Waikiki is the only area of Oahu that has legit nightlife.
Diamond Head
This is where you stay if you want to enjoy everything that Waikiki has to offer, but also want to be able to escape the crowds and noise.
Diamond Head is peaceful and relaxing, with big parks, walking trails, and beaches.
It's just a 20 min walk to the center of Waikiki, but hotels are less expensive here.
Ko Olina
Ko Olina is where you stay if you want to get away from the crowds and stay in a fabulous resort with so many amenities that you'll never have to leave if you don't want to.
It's home to Disney's Aulani and Four Seasons Oahu. There are 4 lagoons that stay extremely calm year round. Keep in mind that most restaurants are in the resorts.
You'll need a car if you want to explore outside the resorts. On this side of the island you'll find Makua Beach, the Pink Pillbox Hike, and the Mermaid Caves.
It's 40 min to Waikiki, 45 min to the North Shore, or 40 min to Kailua.
The west side of Oahu stays dry and sunny. It tends to be hotter over here and it hardly every rains.
North Shore
This is where you stay if you're going to Oahu for outdoor adventure. It's very laid back — mostly small beach towns.
Surf, swim, snorkel, zipline, hike, skydive, ride horses, swim with sharks... The list goes on and on. It's not walkable so you'll definitely need a car to get around.
The North Shore is known as the surf captial of the world because winter brings massive waves and pro surf competitions. Everyone heads to the beaches to watch.
Because of the huge waves, winter is not a good time to swim or snorkel, but summer brings calmer water that's great for playing in the ocean.
There are some iconic food trucks here (like Giovanni's Shrimp and Matsumoto Shave Ice) and some beachfront restaurants, but you won't find much fine dining.
There are only a couple hotels and one major resort (Turtle Bay Resort)
Heads up that there's no nightlife here. It's more of a "go to bed early so you can get up and get outside" kinda place.
Kailua
Kailua is a cute beach town. This is where you go if you're looking for insanely beautiful beaches. Lanikai Beach is regularly voted one of the most beautiful in the world.
Hike to the Lanikai Pillbox for possibly the most breathtaking sunrise on the island. Kayak to the Mokulua Islands to snorkel with turtles and swim in the Queen's Bath. You're also not far from the Kaneohe Sandbar, Byodo-In Temple, or Kualoa Ranch.
There aren't any hotels or resorts but there are some B&Bs.
This side of the island stays warm year round, but the tradewinds keep it a little cooler than the rest of Oahu and it gets more rain and wind during the winter.