Oahu Luxury Vacation Rentals & Villas

Our luxury Oahu vacation rentals span the island, offering a wide variety of choices to travelers seeking that perfect Oahu getaway. You’ll find rentals and villas that exude both the comfort of a private home, but with the posh amenities so deserved when you finally take a break from your busy life. From chef’s kitchens to private lanais overlooking the Pacific, concierge services to arrange your family’s activities to infinity pools, these dream residences make every aspect of vacation a dream. From Diamond Head, known for its posh West Coast feel, to the quieter, more residential feel of Hawaii Kai, Gather’s Oahu vacation rentals truly offer something for everyone. Browse all Oahu vacation rentals below, or choose your favorite Oahu destination to hone in on that perfect location.

Discover popular Oahu destinations

Welcome to The Gathering Place

Known as “The Gathering Place,” Oahu is where you’ll find authentic Hawaiian experiences, from world-class white-sand beaches to bustling urban life to  quieter laidback surf towns. The third-largest of the Hawaiian islands, Oahu has several different regions in which to find your perfect Hawaii vacation rental, all with easy access to the island’s many activities, restaurants and shopping. This is an island where you can feel the pulse of modern life, while still being immersed in the values and traditions of the native Hawaiian people. 

For the best of Oahu Kama’aina (local living), choose a luxury home rental in Aina Haina, known for its emphasis on health, the great outdoors and a close community connection. Families love the area for its easy access to nature, blend of residential and city atmospheres, easy drive to Honolulu and great places to eat. 

Diamond Head is known for its posh West Coast feel – like Beverly Hills and Santa Monica popped up in Hawaii. You get the upscale amenities of those beloved SoCal spots with the beauty and climate of Hawaii – what’s not to love? Visit the famous Sandy Beach to watch body surfers, head into Waikiki for dinner or shopping or go kite surfing along the south shore – this is Oahu living at its most elevated, a place where luxury beachfront homes sell for up to $50 million dollars. Choose an Oahu vacation rental here and avail yourself of all the luxury perks you can imagine. 

Those seeking a quieter, more residential feel and spectacular snorkeling love Hawaii Kai, home to world-renowned Hanauma Bay. Take a morning hike up the challenging Koko Crater Trail for breathtaking island and water views. Choose from single-family homes across from Sandy Beach or multi-million-dollar estates that look out over Honolulu and the west Oahu coastline.  

Everyone loves captivating and charming Kailua for its top beaches and alternative to busy city life. Families adore the small-town feel of the sleepy beach community, known for its crystal-clear, sapphire-blue water, vibrant sunrises over the Mokulua Islands, walking and cycling paths, tennis courts and more. Within the Kailua area, there are luxury vacation rentals also available in Lanikai, originally a planned neighborhood for those seeking quiet weekend and vacation getaways. Today, you can stay just steps from the beautiful beach – plus, with the two Mokulua Islands just offshore, you can kayak right over to them. Swim, golf, hike – all without leaving the neighborhood. 

Oahu vacation rentals on the North Shore offer the timeless appeal of a surfer town, without the city hustle and bustle. Perhaps this is the peaceful Hawiian hideaway of which you’ve been dreaming, famous for its big waves in the winters and calm, warm waters in the summer. There’s a delightfully laid-back, boho vibe here, where the emphasis is on local eats, independent boutique shopping, swimming and snorkeling. 

Whether you’re traveling with friends, family or even pets, these private, luxurious rental homes in Oahu have the upscale amenities you’re hoping for (WiFi, swimming pools, gourmet kitchens) with the comfortable feeling of home. Elevate your stay with private boat charters, guided whale-watching excursions, reservations at the hottest restaurants and most lavish spas – whatever you dream up can be arranged.