Luxury vacation rentals around the world
47 luxury villas and vacation rentals in O‘ahu
1 – 16 of 47 Rentals
Enter dates to see full pricing. Additional fees apply. Taxes may be added. Free cancellation only applicable within 48 hours from booking.
Planning an Oahu vacation? We’re here to help!
The third largest island in Hawaii, Oahu is also the most populous (over 60% of the Island State’s population live here) and home to the state capital, Honolulu. With over 200 miles of palm-tree-lined coastline, Oahu is famous for its beautiful beaches and laid-back way of life. The island first became popular as a vacation destination in the 1920s when the Royal Hawaiian opened its doors and became the first resort hotel in America, and it’s been welcoming tourists ever since. It’s also the birthplace of surfing, with swells reaching up to 30ft in winter. The island has great weather all year round - even in winter, the daily temperature stays at around 80 degrees.
Hike Diamond Head
Offering up spectacular panoramic views of Honolulu and Waikiki beach, a hike to the top of Diamond Head is a great way to get outdoors, get some exercise, and enjoy the natural beauty of Oahu. Although it looks like a long way up, if you choose the right trail you can reach the peak in a little under an hour.
To reach the easiest trail, use the eastern entrance to the park, head for the crater and look for signs directing you to the Diamond Head trailhead. Though the trail is paved most of the way (it was originally built by the US Army), it’s still a good idea to wear sturdy sneakers or walking shoes, and remember to bring water, snacks, and sunscreen. Lastly, don’t rush; take the time to stop at the lookouts along the way for gorgeous views of the ocean and the city spread out below you.
Surf the North Shore
Perhaps the most famous surfing destination in the world, Hawaii’s North Shore is the home of big wave surfing. In the winter months, waves can reach up to 30ft, and the beaches draw surfers from all over, who come to test their skill at competition time. The major draw is the Vans Triple Crown of Surfing, which is held in November and December and has been running since 1983. It’s a great event to watch from the shore, whether you know the intricacies of the sport or not—watching someone take on the iconic Pipeline wave is an experience you’ll remember forever.
If you want to try your hand at surfing more manageable swells, the best waves for beginners and novices are Puaena Point at Haleiwa Beach Park and Kawela Bay. Surfing has its own internal rules—so always let experienced riders go ahead of you and try not crash someone else’s wave.
Shop ‘til you drop
No matter what fashionable souvenir you’re looking for, you’ll find a shop with your name on it in Oahu. From luxury boutiques to wallet-friendly outlet stores and all the big name chains, there’s everything you could think of and more.
Serious shoppers can get their fix at Ala Moana Center in Honolulu. It’s the largest outdoor shopping center in the world, which means you can still catch some rays and top up your tan in between browsing. You’ll find all the major department stores here—including Macy’s, Nordstrom, Neiman Marcus, and Bloomingdales, but for something a little different, make sure you check out Japanese department store Shirokiya, which also has delicious lunch options.
If you more in the market for high-end labels, make a beeline for Luxury Row, located on Kalakaua Ave in the center of Waikiki. You can shop for something sparkly at Tiffany & Co, treat yourself to some Chanel ballet pumps and pick up some shades from Gucci to look good while you do it. There’s also a Sephora for all your beauty buys.
If you love a good deal, the outlet stores at Waikele, 30 mins outside of Waikiki, are sure to please. There are over 50 shops here, including Kate Spade, Barney’s, Coach, and Saks Off Fifth.
Hit the greens
Oahu’s North Shore might be famous for its surf, but it has another string to its bow—great golf courses. At Turtle Bay, you’ll find two excellent choices, one designed by the legendary Arnold Palmer, the other by the equally esteemed George Fazio. Turtle Bay, the Palmer course, is set in 100 acres of unspoiled wetlands and tropical forest so you’re sure to spot a host of different bird and animal species while you play. The first nine holes promise a Scottish-style links experience, while the remaining holes take you through the forest. There are five sets of tees on each hole so golfers of all abilities can challenge themselves and enjoy the course.
The Fazio course is generally considered to be an easier play, and has equally beautiful scenery, running along a coastline lined with palm trees. You’re guaranteed lovely ocean views at every turn. If you prefer to walk while you golf instead of hopping in a cart, the manageable size of the Fazio course makes it an ideal choice.
Experience the luxury of our Oahu vacation rentals
Where to stay: Waikiki
Close to the airport, Waikiki beach and all the shopping and dining options you could wish for, our villas in Waikiki are great for families who like to switch up their activities from one day to the next.
Where to stay: Kailua
If you’re thinking about spacious accommodation right on the beach, then take a look at a Kailua vacation rental . Sleeping up to 18 people, with shaded lanais, swimming pools, and indoor/outdoor style living, if you’re planning a big group getaway there are some great options here.
Where to stay: The North Shore
Does getting up early to hit the waves sound like your kind of getaway? If so, one of our vacation rentals on the north shore of Oahu will be a dream come true. You’ll be able to monitor the weather from the comfort of your lanai, then grab your board and head out in no time at all. Most of our properties in the area sleep up to 10 people, so your buddies can come too, and with gas grills and outdoor dining areas, there’s plenty of space to cook up a feast and relive the day’s adventures over a cold beer.