Who here likes a good staycation? I’m raising my hand! When the HomeAway team challenged us to get away in our own hometown, Dane and I jumped at the chance. There are so many beautiful places to stay on Oahu, but here was our catch – we wanted to bring our dogs. Right away, that took out any high rise apartments in Honolulu that didn’t offer a yard. We looked on the North Shore of Oahu and in Kailua, Oahu and both had absolutely beautiful home rental options. Ultimately we chose Kailua, because the owner accepted pets and we could walk to some of our favorite spots. Today I’m sharing how to spend a weekend in Kailua, Hawaii — where to eat, shop and stay!
How To Spend A Weekend In Kailua
If you aren’t familiar, Kailua is a beautiful beachside town on the east side of Oahu that is filled with delicious restaurants, one-off boutiques and Kailua Beach, which is consistently ranked one of the most beautiful beaches in the world! It’s also where President Obama stays when we brings his family each year 🙂
It’s important to note that there aren’t any big name hotels in Kailua, which is definitely part of the appeal. There are a handful of B+Bs, plus HomeAway rentals. We considered this one, but ultimately chose Holiday Palms. We loved that our rental had a pool, because that’s not something we get to enjoy at our own home, and we definitely took full advantage. It was super dog friendly (not always the norm on Oahu) and had a big yard! #WIN We really like the privacy of i — tucked away from the main road, but everything in Kailua is still walkable.
We spent a lot of the weekend relaxing and just hitting up our favorite spots in the area. And although we spent a lot of our time at the pool, if you plan to visit Kailua, you cannot miss Kailua Beach. It’s truly one of the most beautiful beaches we’ve ever been to and nothing beats the color of the water…
WHERE TO EAT IN KAILUA
Kalapawai Cafe – A super casual eatery that we love for lunch and dinner. Definitely get the browned butter chocolate chip cookie – it’s so dang good! Also, sitting outside puts you in a good spot to enjoy all the resident chickens 🙂
Agnes’ Bakeshop – This place is great for delicious Portuguese donuts, also known as malasadas. Get them hot in the morning + walk over to the beach.
Chad Lou’s – After getting malasadas at Agnes’, get a coffee from Chad Lou’s!
Moke’s Bread and Breakfast – This is a casual eatery + great for breakfast. Request outdoor seating if you bring your pups 🙂
Nalu Health Bar – This is one of my all-time favorite places on all of Oahu, but it’s a great spot for delicious, yet healthy food, that is full of flavor.
Cinnamon’s – One of the most famous breakfast spots on all of Oahu! Go early or else the wait is super long, but be sure to order the Red Velvet Pancakes. They’re very sweet, but nice to share!
Gaslamp – If you’re a cocktail connoisseur, you can’t miss Gaslamp. Make reservations ahead of time and transport back to yesteryear and this super trendy speakeasy that is tucked inside the local pub. We LOVED it!
Over Easy – We LOVE Over Easy brunch, but again – ya gotta get there early! Safe to say we learned out lesson, but the French Toast is out of this world good!
WHERE TO SHOP IN KAILUA
For clothing, I love Betty x Joe, Mahina, Fighting Eel and Bikini Bird.
For home decor, you have to go into Island Bungalow – they have the most swoon-worthy island inspired furniture and decor, plus some delicious smelling oils. I also love the beachy decor in Sand People. If you make it to Sand People, it’s a great place to pick up some fun Hawaii souvenirs. And I would be remiss in not mentioning one of the most awesome boutiques in Kailua – Lauren Roth Art. It’s a beautiful art studio full of color, bright natural light and work from local artists that is nothing short of incredible. Definitely make a point to stop at this gem!
Those these are a few of my favorites, there are so many cute shops to see in Kailua, so heard toward Hekili Street and lose track of time looking at them all! Trust me on this one 😉
If we were staying longer than two days, we would have stocked up at groceries for our HomeAway at the local Whole Foods or Target, but since it was just a short weekend getaway, we decided to take full advantage of the local eateries (10/10 recommend!).
If you are planning a trip to Oahu, I cannot recommend Kailua enough – it is a beautiful beach town and perfect for relaxing. If you’re looking to spend an entire weekend or week there, be sure to consider HomeAway for your time there 🙂