38 Haleiwa Vacation Rentals & Short Term Rentals

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Compare Haleiwa vacation rentals from 8 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $30 to $12000 a night.

Information about Haleiwa

About Haleiwa

Located on Waialua Bay on Oahu’s famous North Shore, Haleiwa is a small surf community with a bohemian personality and lots of character. Known for its phenomenal surfing, as well as the largest and longest-running surf competition series, Haleiwa attracts visitors from around the world. It has also been featured in various movies and is a mainstay in Hawaiian culture. An hour away from Waikiki by car, this is definitely one small town where you won’t experience a shortage of fun activities and things to do.

Things to Do in Haleiwa

There are many fun things to do in Haleiwa whether you’re a local or a visitor. Many people come here for water activities such as surfing, snorkeling, kayaking, and stand up paddle boarding. Check out Ekuhai Beach (Banzai Pipeline Beach), which is the site of the famous Vans Triple Crown surf competition. Surf season runs from October to April, and waves can reach as high as 40-feet. Laniakea Beach is another beautiful local spot where you can catch sight of Hawaiian green sea turtles, and Sunset Beach is a spot famous for its beautiful sunsets. Rent a stand up paddle board or kayak at Sea & Board Sports Hawaii Rental Shop and go for a spin under the famous historic Haleiwa Bridge. Alii Beach Park is a great spot for a picnic and is where Baywatch Hawaii was filmed. Indulge in shave ice at Matsumoto’s, which is a local joint that has been in business since 1950 and is known for serving up some of the best shave ice in town. Downtown Haleiwa has a great shopping scene, from surf shops to artist-owned boutiques, and you can also enjoy a refreshing coconut drink that can be purchased along the side of the road.

Day Trips Near Haleiwa

Just 10 minutes outside of Haleiwa is the Dole Plantation, which is one of Oahu’s most popular tourist destinations. It also contains a pineapple-shaped botanical maze that contains 2.5-miles of maze paths and over 14,000 Hawaiian plants (it was named the world’s largest maze in 2008). Drive an hour south and you’ll end up in downtown Honolulu, where there are many things to do. Lay out at Waikiki Beach, grab a drink at The Royal Hawaiian Hotel, enjoy a deluxe spa treatment at the Abhasa Spa, and check out other points of interest such as the Honolulu Zoo and check out the Honolulu Museum of Art. Another great town to visit is Ko Olina, which is 34 minutes south of Haleiwa and home to Paradise Cove Luau and the family-friendly Disney Aulani Resort & Spa.

Haleiwa Accommodation

Haleiwa has a wide variety of housing available, from large oceanfront beach estates to cute beach shacks with character. There are many older but large multi-acre family estates in the Sunset Hills part of Pupukea, and they all offer stunning ocean views are surrounded by lush nature and fruit trees. Other prime areas to rent an island-style home or condo include the Sunset area of Haleiwa and Velzyland – a more secluded strip that is set apart from the rest of the surrounding area with access to big-wave surfing.

Transportation in Haleiwa

A rental car is the ideal form of transportation in Haleiwa because it will make it easy to travel around the island at your own pace. Taxis are another common but less convenient form of transportation, and many locals and visitors take TheBus, which has multiple routes that service the entire island. You can also rent a moped or bike, but those options are better for short distance travel.

Vacation Rentals in Haleiwa

Find the best Haleiwa vacation rentals with Tripping.com. Choose from 549 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $30 a night to $12000 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 480 of homes in Haleiwa offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 83 rentals with pool or jacuzzi, or relax with the family in one of the 469 homes with cable TV.

For all those dog lovers and cat lovers, Haleiwa offers 19 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 8 rental sites in Haleiwa where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 451 HomeAway rentals, 65 TripAdvisor short term rentals and 21 Booking.com vacation rentals.