Top vacation rental destinations in Oahu, Hawaii

Top vacation rental destinations in Oahu, Hawaii

From buzzing nightlife and boutique shopping, to secluded beaches and swaying palms, Oahu is an island of incredible diversity. There are Oahu rentals to suit every travel style and where you stay will be largely determined by your personal preferences and itinerary. While hot spots like Honolulu and Waikiki are deservedly popular, venturing off the beaten track will take you to gems like Haleiwa, Kailua, and Turtle Bay.

North Shore Oahu vacation rentals

Beachfront bungalow with ocean views and wood décor in North Shore, Oahu

Oahu’s North Shore is one of the most iconic stretches of coastline in North America. Watch local surfers take on monster swells at Waimea Bay or rent a board at beginner-friendly breaks like Haleiwa Beach. Haleiwa Town is a popular base, though you’ll also find secluded North Shore rentals strung along the coast. Wind up a day of sightseeing with fresh coconuts and locally-grown pineapple on your private deck.

Waimea Bay, North Shore vacation rentals

Waimea Bay is a mecca for big wave surfers and boasts record-setting swells of more than 50 feet. In the winter, beachfront cottages and studios are snapped up by diehard surfers planning to take on Pipeline and other legendary breaks. Not interested in riding monsters? Visit in the summer and you can snorkel with Hawaiian sea turtles and check out nearby attractions like the Polynesian Cultural Center.

Kailua, Hawaii vacation rentals

Kailua, a laid-back town on the island’s east coast, is a fantastic base for exploring Oahu. Spend the day sunbathing on Lanikai Beach or relaxing by the pool of your Kailua, Kona vacation rentals villa. Self-contained kitchens are a great excuse to stock up at the Kailua Farmers Market and prepare your own island-inspired meals. Think tuna poke bowls, fresh-baked banana bread, slow-roasted pork, and tropical fruit smoothies.

Turtle Bay vacation rentals

Turtle Bay is a North Shore favorite, luring sunseekers with golden sand and jewel-toned water. Condos appeal to budget-conscious vacationers and include access to public pools, tropical grounds, and outdoor grilling areas. Golfers snap up condos near the championship courses at Turtle Bay Resort, the best boasting fairway views. Turtle Bay is also a bastion for luxury Oahu vacation rentals, including dreamy oceanfront villas and deluxe beach bungalows.

Oahu vacation rentals for large groups

Luxury oceanside mansion with tropical yard in Oahu, Hawaii

Oahu is known as the “Gathering Place” so it’s only fitting that the island is a popular destination for family reunions, corporate retreats, and group getaways. With many properties sleeping more than 20 guests, vacation home rentals in Oahu, Hawaii make it easy to host large groups. Luxury houses for rent in Oahu provide a dream setting for tropical weddings – think poolside rehearsal dinners, barefoot beach ceremonies, and al fresco sunset receptions.

Party beach house rentals in Oahu

With buzzing nightlife and gorgeous beaches, Oahu lends itself to celebrations of all shapes and sizes. Popular with bachelor and bachelorette parties, North Shore rentals offer spacious living areas that are perfect for hosting mimosa-soaked brunches and private poker nights. Homes for rent in Oahu are also snapped up by spring break partygoers with their sights set on boozy catamaran cruises and sun-soaked days at Wet n’ Wild Hawaii.

Oahu luxury vacation rentals

Luxury bedroom with tropical décor and freestanding bath in Oahu, Hawaii

Planning an extravagant island getaway? With Oahu vacation rentals by owner you can unlock access to some of the island’s most luxurious properties. Stay close to the action with penthouse apartments in Waikiki or lock in a week of R&R at a gated oceanfront estate or farm-style home. You’ll love basking by the palm-fringed swimming pool, enjoying al fresco meals on the deck, and letting yourself melt into island time.