The Best Vacation Rentals on Oahu’s North Shore

Choosing a vacation rental on Oahu’s North Shore offers a unique Hawaiian experience that you won’t find in traditional hotel stays. Nestled in a laid-back, natural setting, these rentals provide the perfect blend of privacy, comfort, and local charm. Whether you’re staying in a beachfront cottage or a cozy home near the lush mountains, you’ll have more space to relax, cook your own meals, and truly immerse yourself in the island’s beauty. Plus, you’ll be just steps away from the world-famous surf spots, pristine beaches, and the vibrant community that makes the North Shore so special.

The Best Family Beach House Rental

Pupukea Complex: Located in Pupukea, one of the North Shores most histroric towns, this 10 person retreat is the ideal location for any large group or family. With a huge yard, tennis court, and massive deck this fully fenced property is the perfect blend of common space and private getaway for the entire family.

The home includes 3 bedrooms, 3 bathrooms, family room, and a deck that opens up to the ocean! The house comes with A/C in the 2 upstairs rooms and a/c downstairs as of 4/18/22, but with the doors opened up, who needs it! There is a well maintained landscaped acre of land for you to play on, even your own private “Pickle-ball or mini-tennis” court, and watch the magnificent sunsets from the open lanais!

Fully furnished and well decorated, the attention to detail makes this house feel like “home.” Bedding arrangements include a King bed in the Master, a King with 2 Twins in upstairs guest bedroom, and 4 Twins in the downstairs. **The downstairs has its own separate entrance. The kitchen is fully equipped with with everything you would need to cook for the family and eat in this beautiful house!

The Most “Hawaiian” Vacation Rental On Oahu’s North Shore

Ocean Front Rocky Point Hale: The Rocky Point Hale is a quintessential North Shore custom built luxury home located at the peak of the famous Rocky Point surf break. The home is situated in a private setting on the point out of view of ocean goers and public beach accesses, yet its location allows guests to view the beaches and the surf from Pupukea to Sunset Beach. Be in the mix on the oceanfront and away from it all at the same time.

The spacious home is situated on over 7,000 square foot of oceanfront property, surrounded by lush vegetation. Custom built by local builder, the environment is incorporated into its design, mixing modern luxury with the simplistic beauty of the oceanfront lifestyle. Return home from a surf, snorkel or beach walk to sit on the lanai with wrap around bench seating or enjoy the sunset from the “surf check deck” nestled in the naupaka bush.

There are four bedrooms; on the second floor is the master bedroom with its own lanai and seating area, two King en-suite’s and one King en-suite on the first floor. In two of the bedrooms there are additional twin beds. Also with 6 bathrooms, the Rocky Point Hale offers more than spacious accommodation for up to 10 guests. Downstairs also features a mauka (mountain) facing living room with kitchenette.

This vacation hale is ideal for a surf trip or oceanfront retreat in Hawaii, or a large family vacation on Oahu. Enjoy dining at home and creating fresh island themed meals in the fully equipped gourmet kitchen, relax in the bountiful indoor living spaces, and decompress with a cocktail at sunset overlooking the most beautiful beaches in Hawaii. Celebrate the day with a marvelous sunset, after enjoying the crystal blue ocean diving, swimming or surfing. Spend a memorable Oahu vacation at home, and venture in ease to nearby towns of Haleiwa, Kahuku Turtle Bay and Waialua for shopping, restaurants and ocean activities on the North Shore of Oahu.

This property may not be rented for less than 30 consecutive days

The Most Luxurious North Shore Vacation Rental

Waialua Beachfront Estate: This Waialua vacation rental home on Oahu’s North Shore features direct beach access, a private pool and hot tub, air conditioning, and a fantastic location convenient to beaches and a variety of island activities.

MAIN HOUSE
The open kitchen at Kala`iku has extensive counter space, two sinks, high-quality stainless steel appliances, and bar seating, making it easy to enjoy meals at home. A dining space with a gas fireplace and a wall of custom pocket doors flows out to an open-air dining area, or into a comfortable living space with plenty of seating and a sizable television. Downstairs, another common area provides an additional sectional sofa and television, as well as a ping pong table. Amenities such as wireless internet, cable, a DVD player and DVD library, a stereo, a washer and dryer, and a dedicated kids’ playroom ensure total guest comfort throughout your stay.

Kala`iku’s ocean-view primary suite boasts a California king Tempur-Pedic bed, private lanai, fireplace, 55-inch television, huge walk-in closet, and en suite bath with jetted tub, separate shower, and dual sinks. An ocean-view junior primary has a queen-size Tempur-Pedic bed and its own lanai, 55-inch television, and en suite bath with jetted tub and shower. The third and fourth bedrooms, which share a Jack-and-Jill bathroom, each have a double bed, lanai with mountain views, television, and desk. The fifth bedroom has a queen-size sleeper sofa and mountain views, but also makes a perfect media room, thanks to its 75-inch television.

Step outdoors at Kala`iku to find your sparkling pool with a safety fence, hot tub for eight, barbecue grill, and children’s playhouse, slide, and swings. Direct beach access leads to the golden sand and brilliant blues of the ocean just beyond, where a protective reef makes for excellent swimming and snorkeling.

GUEST COTTAGE
This one-bedroom, one-bathroom home features an outdoor courtyard, outdoor shower, and outdoor seating enough for 5.

Inside the French doors, you walk into a full kitchen with an apartment-sized stove and refrigerator, custom cabinetry, and stone countertops. Ahead you will find a living area with a sofa that can pull into a queen sleeper and a custom twin-size trundle bed for extra guests. Going up the custom spiral staircase you come to the main bedroom loft featuring a desk area, tv, and California king sized bed. Stay cool with the split AC unit or many windows that allow the ocean breezes to flow through. Great for a small family or couple looking for a getaway.

The Most Romantic Vacation Rental On The North Shore

Haleiwa Waterfront House: With sweeping views of the Pacific Ocean this rental is located perfectly in the historic Haleiwa town. Minutes away from dining, shopping, and world class surf. The space

The spacious open living, kitchen and dining area will make you feel right at home. Barbecue and relax on the lanai with spectacular sunsets on the water. Enjoy the sweet sounds of the ocean from anywhere in the house. The house was remodeled inside/out in 2020 with all new furniture. Air conditioning throughout the house including the bedroom. Sleeps 2.

What to do on the North Shore?

The north shore has so much to offer. World class surfing, food, hiking & shopping. If your staying busy, chances are you will need a kick of caffiene to keep your fun going. Check out our list of favoirte North Shore Coffee shops.