Planning a perfect Hawaii beach getaway on Oahu's North Shore

How to luck out with your own dream Hawaiian family retreat.

March 3, 2017 at 1:30PM
Morning joggers on the beach on Oahu's North Shore. (Brian J. Cantwell/Seattle Times/TNS)
Morning joggers on the beach on Oahu’s North Shore, near the laid-back town of Haleiwa. Photos by BRIAN J. CANTWELL • Seattle Times (The Minnesota Star Tribune)

"Could this be more perfect?"

My family and I couldn't stop turning to each other and saying that the first evening of our October vacation in Haleiwa, Hawaii, as we sat around an umbrella table on our rented beach cottage's wooden deck, 20 feet from the sand.

We sipped homemade mai tais made of canned Hawaiian Sun lilikoi drink purchased at the Foodland supermarket just up the road. Topping the cocktails were splashes of light rum and black rum, garnished with a wedge of fresh pineapple, a slice of lime and — we found them in our perfect beach cottage's kitchen cupboard — little paper umbrellas.

We took in the view of palm trees, golden sand, azure waves, surfers and the setting sun, and asked again, "Could this be more perfect?"

Travel can be about exploring other cultures, and that can be a richly rewarding reason to go. Travel can be about adventure, hiking or paddling in some exotic setting. It can be about trying new foods, or sipping wines from a famous vineyard.

And sometimes travel can be about teaming up with your daughter and her boyfriend to finish a challenging 1,000-piece jigsaw puzzle before you have to pack up and go home.

That last one was a key part of our vacation, which was, in the bigger picture, all about reconnecting with family.

It happened in a classic Hawaiian rental cottage on one of the most beautiful beaches anywhere, and I highly recommend the experience.

Here are some thoughts about what made this getaway among the best ever, and how to do it yourself.

My Seattle-based daughter and her partner, both 25, had been traveling and working in Australia and New Zealand for 14 months. They had just completed a winter of work at a New Zealand ski area. My wife and I missed them, they felt ready to come home, and meeting them on their way back, in Hawaii, seemed like a dandy rendezvous.

The North Shore of Oahu was our pick, for relatively easy access to Honolulu International Airport while retaining a low-key, surfer-culture vibe.

I spent hours combing vacation-rental websites. I finally zeroed in on a two-bedroom beach cottage, of maybe 1950s vintage, on a famous surfing beach. VRBO.com listed it for about $300 a night, rented by the week.

I usually spend less on lodging. But I don't usually stay in beachfront accommodations with the ocean roaring all night outside my open window. In Hawaii it's easy to spend much more. This place was a find.

Sweetening the deal: I knew from previous visits that a pleasant 3½-mile bike path parallels the main road along the North Shore, including where this rental was situated. One of my good ideas before leaving home: I went online and found a bike-rental outfit that would deliver bicycles to our lodging.

Some tips on planning your own perfect family retreat on Oahu's North Shore:

Don't overplan. Give yourself at least a week, healing you of hometown stresses and letting you all get reacquainted — whether you're strolling the beach with a cup of coffee at sunrise, sipping a Kona Brewing longneck over a card game on the lanai, or dipping toes in the surf as the full moon rises over the Pacific (yes, check the moon schedule before you book!).

Enjoy those bikes. We parked the rental car for most of the week and biked to Shark's Cove snorkeling beach, or to the supermarket, or to get shave ice. The bike delivery folks were helpful, friendly and punctual, and our bikes came with locks, helmets and removable baskets that could be used while shopping as well as for toting groceries home (northshorebikerentals.com).

Eat well. Rent a place with a good outdoor grill. (Our cottage had a choice of propane or charcoal.) Sometimes you'll see fishermen along the road with an ice chest of fresh ahi for sale. And there's a farmers market in Waimea Valley on Thursday afternoons (farmloversmarkets.com/haleiwa-farmers-market) where you can stock up on local papaya, bananas and dragon fruit, a hot-pink-skinned fruit that tastes like a cross between kiwi and watermelon.

We also biked to breakfast at the famous Ted's Bakery, the only restaurant where I have ordered fried Spam (with fried rice and eggs). We returned to the cottage with one of Ted's trademark Chocolate Haupia pies, with dreamy-creamy layers of chocolate and coconut ($12.88, tedsbakery.com).

Let serendipity work its magic. When we saw a green coconut freshly dropped from a palm in front of our cottage, I acted on a hunch and went to search the cottage's tool shed. Sure enough, there was a machete. Every Hawaiian gardener's "go-to" tool, it was just the thing for lopping the top off a coconut so we could sip the cool, refreshing water inside.

Make your own music as the sun goes down. An ukulele is easy to carry with luggage, my daughter found. Or buy one in Honolulu, where locals make some of the world's finest handcrafted ukes (see koaloha.com or kamakahawaii.com).

Bring your favorite old beach films; most vacation rentals have DVD players. Enjoy movie-and-popcorn nights. (Our perfect cottage had DVDs of famous surfing footage.)

Bring your favorite card games. We relearned how to play Uno, which was on the game shelf in our cottage.

Watch the surfers. They were catching waves right in front of our place, morning till night. Slather on the sunscreen, kick back on a lounge chair and enjoy the action. In winter, the surf here can be as high as a house. (For a first-timer lesson, try Waikiki, where the waves are tamer.)

Mostly, just relax and get to know yourselves again. I've traveled to many wonderful places and had excellent adventures. But this was the best pure vacation I've had in years.

Finding the perfect beach rental

I used HomeAway.com and its partner, VRBO.com. They're very similar, but I prefer VRBO's filter setup — you can easily specify a beachfront location, the maximum rent you want to pay, and amenities such as an outdoor grill, internet access, etc.

Both sites include a booking service fee, averaging 6 percent, that isn't clearly listed, and almost all rentals add cleaning fees on top of the listed rental price. When you book and pay through these two websites, you get protection of your full rental payment against listing fraud, phishing, "significant" misrepresentation and more.

I always feel most comfortable if the property owner or manager responds quickly. I like to speak to them by phone so I get a clear feeling that they are who they say they are.

I've had better luck with VRBO and HomeAway than with Airbnb. With Airbnb, I've seen more misrepresentation by landlords — such as the Kauai rental that claimed to be a peaceful riverside walk from the ocean but turned out to require hiking the narrow shoulder of a busy highway. With any online offering, carefully inspect photos and read reviews (recent reviews are best). Try to get a street address so you can use Google Street View and see the neighborhood. If anything feels fishy, ask the landlord for references and make more calls.

On the North Shore of Oahu, you rarely need air conditioning; just open windows and let the trade winds blow through. And maybe, for this week of reconnecting with your family or friends, you really don't need internet. (Unplug, you might like it.)

More about Oahu's North Shore

The laid-back town of Haleiwa ("haw-lay-EE-va") is the focal point of Oahu's North Shore. It's about 40 minutes, via the H2 freeway and Hwy. 99, from Honolulu International Airport. Or take the less direct, slower and much more scenic Hwy. 83 (Kamehameha Highway) along the island's windward shore through Kaneohe and Kahuku (allow 90 minutes or more).

Art walk: Every second Saturday, from 3-7 p.m., is Art Walk evening in Haleiwa. Galleries and shops stay open late and you can meet local artists (gonorthshore.org/haleiwa-art-walk).

Historic walking tour: Take a 90-minute walking tour of historic Haleiwa. Tour by appointment (at least 48 hours' notice needed): $10. Visit Haleiwa Shingon Mission, Lili'uokalani Church, Waialua Court House and more. See gonorthshore.org/history-and-tours.

More information: gonorthshore.org.


A surf shop in Haleiwa, on Oahu's North Shore. The town is the anchor community for this more laid-back side of Oahu. (Brian J. Cantwell/Seattle Times/TNS)
A surf shop in Haleiwa, on Oahu’s North Shore. The town is the anchor community for this more laid-back side of Oahu. (Brian J. Cantwell/Seattle Times (The Minnesota Star Tribune)
Figure out what makes you happy and search the internet to find your perfect beach rental. (Brian J. Cantwell/Seattle Times/TNS)
Figure out what makes you happy and search the internet to find your perfect beach rental. (Brian J. Cantwell/Seattle Times (The Minnesota Star Tribune)
Our perfect beach cottage came equipped with beach chairs, a beach umbrella and basic snorkel gear. Buy a couple of $4 inflatable swim rings at any ABC Store and you're all set. (Brian J. Cantwell/Seattle Times/TNS)
Our perfect beach cottage came equipped with beach chairs, a beach umbrella and basic snorkel gear. Buy a couple of $4 inflatable swim rings at any ABC Store and you’re all set. (Brian J. Cantwell/Seattle Times (The Minnesota Star Tribune)
Rented cruiser bikes and a paved bike path are a great way to get around on Oahu's North Shore. (Brian J. Cantwell/Seattle Times/TNS)
From top: Figure out what makes you happy and search the internet to find your perfect beach rental, like this cabin found on VRBO.com. The author’s perfect beach cottage came equipped with beach chairs, a beach umbrella and basic snorkel gear. Buy a couple of $4 inflatable swim rings at any ABC Store. Rented cruiser bikes and a paved bike path are a great way to get around Oahu’s North Shore. (The Minnesota Star Tribune)
A homemade mai tai and a sunset view of surf from our North Shore beach cottage. (Brian J. Cantwell/Seattle Times/TNS)
A homemade mai tai and a sunset view of surf from our North Shore beach cottage. (Brian J. Cantwell/Seattle Times (The Minnesota Star Tribune)
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Brian J. Cantwell, Seattle Times

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