9 Oahu Vacation Rentals for Your Next Beach Escape to Hawaii

Aptly named, Turtle Bay Resort maintains the untamed spirit of the North Shore. It’s on a breezy peninsula of land, surrounded by a timeless and majestic ocean. Rent out a spacious villa there, like Direct Ocean View Beach Level 3bed Villa 103, where you only have to cross 20 yards of lawn to get to the beach.

In addition to the villa’s luxuries, like a gourmet kitchen and large lanai (porch) for outdoor dining, you can enjoy the resort’s amenities, including 10 tennis courts, stand-up paddle lessons and tours, a day spa, and an oceanfront pool and bar.

The Apartments at the Ilikai are located inside one of the most iconic buildings in all of Waikiki. If it looks familiar, the swanky high-rise makes a cameo in the opening credits of both the classic and rebooted TV show Hawaii Five-O. Strike a pose on your own private balcony, or head downstairs to enjoy Eggs Benedict at Cinnamon’s, a local breakfast favorite that has an outpost in the Ilikai.

It’s only a short stroll over to Ala Moana Beach Park, a half-mile-long beach that is especially popular with picnickers and swimmers, as it is well protected. Ala Moana Center, the world’s largest outdoor shopping center, is a 15-minute walk or very short drive away.

For an off-the-beaten-path location, this North Shore Oahu-Large 1 Br-Steps to Beach is in Waialua, an old sugar-cane growing town with a historic mill. It’s still close to a beach—located less than 200 feet away—and it’s only a short bike ride into Haleiwa, the main hub of the North Shore. There you’ll find shopping, restaurants, and plenty of equipment rental outfits to pick up SCUBA gear or rent a stand-up paddleboard.

With epic wave action in the winter at spots like Sunset Beach, Pipeline Beach and Waimea Beach, Oahu’s North Shore is known as a mecca for professional and pro-level surfers. Watching them slide down a wave is awe-inspiring. In the summer months, the scene flips: The water is glassy and flat, making it ideal to snorkel among the gentle giant sea turtles who congregate in the water here.

Kailua is on Oahu’s Windward side, about 20 minutes from downtown Honolulu but a world away in vibe. It’s a relaxed, seaside town where kite surfers and canoe paddlers zip by atop turquoise waters.

The Beachfront Home, Steps to Kailua Beach vacation rental is on a grassy acre of land with a coconut grove. As the beach, here is the main attraction, and only a minute or so walk away, there are plenty of beach toys on hand. Two lanais (porches) are upstairs in the home, offering views of the Koolau Mountains and the ocean, and there’s another lanai downstairs out the bedroom. There is also plenty of room for entertaining, with a large dining room.

Well art-directed and compact, the Tropical Studio in Heart of Waikiki is in a central location, making it easy to either get to the beach, or to head around the back of Waikiki along Ala Wai for easy access to nearby destinations. The ample kitchen makes staying in this studio even more affordable, while a pool and a balcony still make you feel like you are living large.

Once you visit Waikiki’s beach, you’ll understand why it has inspired thousands of songs. The surf rolls in consistently and gently, and the warm is bathtub warm, creating ideal conditions for outrigger canoe paddling or surfing lessons. Insider’s tip: Get up early for a hike up Diamond Head while the air is still cooler, then hit the beach for a swim in the afternoon.

If the bustling crowds aren’t your thing, escape to Oahu’s west side. Here, the weather is consistently warm and sunny, with little rainfall, making every day is a good day for poolside lounging or a jaunt to the beach.

When staying at the Marriott Ko Olina Timeshare Villa Resort, the question isn’t “Should we go to the pool?” but rather, “Which pool are we in the mood for?” There’s a quieter adult pool for lap swimming, a family-friendly lagoon, and for the littlest vacationers, a kiddie pool. Outdoor grills, washer/dryers in the units, and great views add up to a paradise for travelers.

Beach coves in Ko Olina are excellent, but if you do somehow summon the will to leave the resort area, nearby Yokohama Bay has a beach so secluded, you may have it all to yourself.

Right off of Waikiki’s main thoroughfare, the bustling Ala Moana Boulevard, this Beautiful and Well Located at Aqua Palms vacation rental is inside a stylish boutique hotel.

It’s within walking distance of the beach, restaurants and nightlife, or you can take the Waikiki Shuttle for even more shopping and sightseeing. Kick back and enjoy the amazing view from the sundeck, which has barbecue grills and a pool.

Right in the heart of the business district, the Aston At The Executive Centre is ideal for travelers interested in the Historical Culture and Arts District.

Browse the many nearby art galleries, or check out the collections at the Hawaii State Art Museum and the Honolulu Museum of Art. On First Fridays of each month, Chinatown throws a party of epic proportions, where the art spaces, bars, boutiques, studios, tattoo parlors, and restaurants all collaborate on a theme, and people hop from spot to spot enjoying the action.

If you’re into the contemporary art scene, be sure to check out the nearby neighborhood of Kakaako, which has Instagram-worthy murals on the buildings, courtesy of a yearly art festival.