Hey mc,
Kailua is a car ride of about 20 minmutes from Waikiki to Kailua where all the kiting is. Waikiki or Haliewa are the touristy shopping type places neither of which are kiteable. Haliewa is the main surf town where pipe and sunsets and Waiamea are.
Kailua is a sleepy little suburb right on the best swimming beaches in Oahu, it's also right next to Lanikai which is the richest suburb in Oahu where all the stars go to rent and holiday. There's just your usual shopping centres nearby but not aimed at the tourist.
At Kailua there is a heap of stuff to do and there are some really nice restaurants and bars in Kailua but no hotels. All acomodation is beach rentals by private letting from owners. They are easy to find if you do a google search. You can swim, snorkel, sea kayak to the Mokoluas and around flat island and rent windsurfing/kitesurfing gear etc.
To stay sane, I would recommend relaxing and staying in Kailua and using a car to get over to Waikiki and Haliewa when you want to hit the town or go shopping otherwisee living there is like being in a tourist trap (for me anyway). Don't leave anything of value locked in your car on the north shore unless you want it nicked.
Most of the people who want to swim and snorkel get tours from Waikiki to Kailua or Honaleia Bay as the beaches on Waikiki are a bit ordinary and are usually fairly crowded in cmparison to Kailua.
"Mokes" is a 50 minute car ride from Kailua up the freeway or take an hour and a bit and take the north coast road and see some of the more beautiful parts of Oahu, plenty to sight see and do. There are numerous other spots on the North East coast as you drive around towards the North where you can kite also like Goat Island, Chinamans Hat etc (ask locals).
There is wakeboarding in Kaneohe Bay (next bay round to Kailua Bay)and lava tubes and staircases to climb (Stairway to heaven), plenty to do if there is no wind. I rate Oahu over Maui for all round entertainment and kiting conditions and variety.
Do a Google search.
Have fun
