The Best Vacation Rentals to Book on Oahu, Hawaii

This 37th-floor condo boasts striking views of the lush Ko’olau Mountains. Get cooking Hawaiian-style with the rice cooker in your fully equipped kitchen, or laze by the heated outdoor pool and watch the kids on the climbing frame. If you decide to spend your day out and about, you can walk to Kalakaua Avenue, Waikiki Beach and the Duke Kahanamoku Statue.

While this condo comes with many amazing amenities, from an outdoor pool to bike rentals, the main highlight of this Oahu vacation rental is the location. Situated right on Kalakaua Avenue, you’ll have easy access to over 300 shops. Buy everything from opulent jewelry to beach essentials, before spreading out your new gear over 400sqft (37sqm) of floor space.

Located on the golden shores of Sunset Beach, this quirky blue-roofed Oahu beach bungalow holds a prime piece of real estate on Oahu’s North Shore. Each morning, you can wake up from a king-sized bed and watch the talented surfers ride tall waves from your beachfront deck. And each evening, you can finish your day with a pastel-colored sunset.

In 1964, the Ilikai opened its doors and became the first luxury high-rise hotel in the Hawaiian Islands. Since then, the Ilikai has welcomed hundreds of celebrities, from Dolly Parton to Elvis Presley. Perhaps you’ll see a few A-listers lounging in the calm and clear waters of nearby Kahanamoku Beach, or receive the star treatment yourself at the on-site Cinnamon’s restaurant.

At this Oahu vacation rental, you’ll be able to admire the sparkling Pacific Ocean from your private lanai. And, if you’d like to take a dip, Kuhio Beach is just a block away. Once you’re done exploring, come back to this eighth-floor condo to relax. Cook up your favorite meal on the range, and zone out in front of the TV – Hawaii is all about chilling out.

Affordable gems, including the Royal Kuhio, are tucked between Oahu’s pricier vacation rentals. For the Royal Kuhio’s budget-friendly price, you’ll still get to lounge on relaxed island-style furnishings, make a hot cup of Maui coffee in the coffeemaker, admire city views, take a dip in the L-shaped pool and explore Waikiki’s best shops and restaurants.

This Hawaiian plantation-style home has been owned by the same family since it was purchased from the Queen of Hawaii, long before Hawaii became a state. Today, you can still see elements of Hawaiian plantation-style architecture in this minimalist Oahu bungalow – from the wooden frame to the large, covered lanai. The pool and built-in hot tub makes the garden a wonderful place to spend an afternoon. And to round out your taste of Hawaii life, you can spend a day at the nearby Kailua Beach.

This is arguably the coolest holiday home on Oahu. This fairytale-esque vacation rental resembles a gingerbread house of Germanic yore, complete with an icing-like trim and multiple chalet-style roofs. Go inside, however, and it’s a 21st-century paradise: numerous squishy sofas face a widescreen TV, marble dining shelves face out to the ocean, and there’s a big chrome BBQ outside. Situated between Diamond Head and the hidden Tonggs Beach, you really can’t ask for a better spot.