The Best Vacation Rentals to Book on Oahu, Hawaii

After a shopping spree on Kalakaua Avenue, relax by the pool at Luana Waikiki Hotel and Suites
After a shopping spree on Kalakaua Avenue, relax by the pool at Luana Waikiki Hotel and Suites | Courtesy of Luana Waikiki Hotel and Suites / Expedia
Photo of Sarah Etinas
2 December 2021
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Oahu, Hawaii is one of the most scenic vacation destinations in the world. Home to Waikiki Beach, Diamond Head, the North Shore and Pearl Harbor, there’s much to see and do on this beautiful island in the 50th state. Here are a few of the best Oahu vacation rentals for for your island getaway, all bookable with Culture Trip.

Mountain View Condo at the Aston at the Waikiki Banyan, for a home base in Waikiki

View of Waikiki high rises and ocean from a high-floor balcony at the Aston at the Waikiki Banyan
Courtesy of Aston at the Waikiki Banyan / Expedia

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.

Studio Condo at the Luana Waikiki Hotel & Suites, for a shopping spree in Waikiki

Pool area surrounded by greenery at Luana Waikiki Hotel and Suites
Courtesy of Luana Waikiki Hotel and Suites / Expedia

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.

Grand Penthouse at the Waikiki Landmark, for a vacation splurge in Waikiki

View from above of the large amoeba-shaped pool at Grand Penthouse at the Waikiki Landmark on Oahu, Hawaii
Courtesy of Grand Penthouse at the Waikiki Landmark / Expedia

The Waikiki Landmark is one of the most extravagant condominium buildings in Waikiki. The three pools, two hot tubs and prime location in Waikiki’s shopping district are just the start of the fantastic features. When you book a stay at the huge Grand Penthouse, everything gets bigger and better: enjoy contemporary industrial-chic decor in this corner condo with a deep porcelain tub and floor-to-ceiling glass windows offering jaw-dropping ocean views.

Four-Bedroom Blue Mahina Home, for beachfront luxury at Sunset Beach

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.

One-Bedroom Condo at the Ilikai Hotel & Luxury Suites, for a slice of celebrity history in Waikiki

Overhead shot of the pool area at Ilikai Hotel and Luxury Suites
Courtesy of Ilikai Hotel and Luxury Suites / Expedia

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.

Ocean View Condo at the Aston at the Waikiki Banyan, for striking ocean views in Waikiki

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.

Royal Kuhio, for more affordable lodging in Waikiki

Aerial view of Waikiki Beach and Diamond Head on Oahu, Hawaii
Courtesy of Royal Kuhio / Expedia

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.

Renovated 1937 Hawaiian Plantation Home, for a taste of local life in Kailua

Bungalow with a covered lanai, pool and built-in hot tub of 1937 Hawaiian Plantation Home on Oahu, Hawaii
Courtesy of 1937 Hawaiian Plantation Home / Expedia

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.

Elaborate Gingerbread-Style House, for lavish living in Honolulu

Large lanai right on oceanfront of Elaborate Gingerbread-Style House on Oahu, Hawaii
Courtesy of Elaborate Gingerbread-Style House / Expedia

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.

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