We Found 8 of Oahu’s Very Best VRBO Hawaii Vacation Homes

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The Hawaiian island of O’ahu (Oahu) is also known as “The Gathering Place.” The third-largest of Hawaii’s eight major islands, vacationers flock to Oahu for cosmopolitan Honolulu, the beautiful beaches, and variety of nature trails. It’s no wonder we were easily able to find the best Oahu VRBO vacation rentals for your next trip to Hawaii.

Oahu is home to the vibrant city of Honolulu, Hawaii’s state capital and the most remote city of its size in the world. There are so many things to do in Honolulu, from gourmet international cuisine to historic landmarks. No trip to Oahu is complete without visiting Pearl Harbor and relaxing on the famous Waikiki Beach! Beyond the buzzing capital, there are even more things to do in Oahu, like exhilarating helicopter tours, a variety of water sports, and excellent hiking/biking inland.

Whether you choose to stay in downtown Honolulu, close to Waikiki Beach, or on the stunning North Shore, we can help you find the best Oahu VRBO home for your next trip to Hawaii. Check out our curated list below and start planning your adventurous Oahu getaway today!

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8. Architect-Designed, Luxury Honolulu Beach Condo

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This fantastic luxury condo in Honolulu overlooks Ala Moana Beach Park, offering special ocean views from its open living space and large balcony.  With two big bedrooms and 2.5 modern bathrooms, the condo can easily accommodate a group of 4, making it ideal for a romantic couples getaway or small family vacation. The spacious and open lanai is a standout feature, offering a barbecue grill, ample seating, and a private spa with beautiful views of the park and ocean.

Designed by a renowned architecture firm, the interiors feature luxurious Italian furniture and stylish, modern decor. Large glass windows let in tons of natural light and perfectly frame the stunning park and ocean views from inside the open-concept living/dining/kitchen. The bedrooms feature enormous walk-in closets that invite you to unpack and make yourself right at home. This ultra-luxurious condo VRBO in Honolulu is available for an average $2,000 a night.

7. Oceanfront VRBO Oahu North Shore Home For Beach Bums

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Imagine waking up, rolling out of bed, slipping through a sliding glass door, and feeling your toes hit the sand and surf, all in under 30 seconds. This is your reality when you book this stunning oceanfront VRBO Oahu North Shore home! This oceanfront location is just unbeatable. Step out onto your private, shaded lanai and hit the beach in seconds. Chill out and relax with an outdoor BBQ and lots of seating, perfect for enjoying those enviable ocean views.

Perfect for beach bums and surfers alike, this charming oceanfront home can accommodate a group of 4 with two bedrooms and one bathroom. There’s plenty of space to stretch out and hang out together inside, including an open-concept living room with large sectional and flat screen TV. The modern kitchen is well-equipped with everything you need to self-cater during your vacation, but you might equally enjoy the North Shore’s many delightful beachfront restaurants and cafes instead. This upscale surfer’s paradise can be yours for an average of $460 a night.

6. Huge North Shore Oahu Estate On Sunset Beachnorth shore oahu estate airbnb north shore oahu estate airbnb north shore oahu estate airbnb

Available for an average of $595 a night, this luxury beachfront estate on Oahu’s North Shore is sure to impress your entire group. This paradise on Sunset Beach can accommodate up to 6 with two big bedrooms and three modern bathrooms. The property sits on 55+ feet of white, sandy beach and boasts impressive 180-degree ocean views throughout every room.

Enjoy gathering together in the open, airy living space, which flows naturally out onto a huge patio with even more space to entertain. The gourmet kitchen is fully equipped, ready for you to sit down for a meal together in the dedicated dining space.  High, vaulted ceilings with exposed wood beams keep every room feeling open and airy. Upstairs, the master bedroom has sliding glass doors which lead to a private balcony overlooking the sandy beach and bright blue ocean. This enviable address is located on one of the most desirable stretches of beachfront coastline, just a short walk to Waimea Bay and the famous Teds Bakery in town.

5. Ultra-Luxurious, Private Beachfront 11,000+ Sq.Ft. Mansion

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They say, “size doesn’t matter,” but if you have a huge group of friends or family traveling to Hawaii together, this enormous luxury mansion in Kailua, Oahu could be just right. Enjoy direct access to the sandy beaches of beautiful Kailua from this prestigious, sprawling estate. The main residence has five bedrooms and 11,000 sq.ft. of lavish, tropical living, in addition to a separate three-bedroom guest house. That’s plenty of room to accommodate 16 guests, making this luxury mansion perfect for your next family reunion, pre-wedding events, or big, blowout vacation with friends.

All that space and luxury does come at a price. If you can swing the $15,000 a night average rate, you won’t be disappointed! This massive estate includes a grotto-style resort swimming pool with hot tub, waterfall, and outdoor cabana, while the interior’s attention to detail and fine craftsmanship are evident throughout. Did we mention the spectacular ocean views? Enjoy waking up to crashing waves and swaying palm trees each and every day. This is truly one of the best Oahu VRBO vacation rentals available.

4. Family-Ready Ko Olina Penthouse With Ocean & Mountain Views

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Located just 20 miles from Honolulu International Airport on the beautiful southwestern shores of Oahu, this family-friendly Ko Olina penthouse VRBO offers stunning ocean and mountain views. While convenient to the airport, Ko Olina is a luxurious and idyllic beachfront community that offers total relaxation in contrast to busy downtown Honolulu. Though private and remote-feeling, Ko Olina is actually just minutes away from tons of shopping, dining, and nightlife in nearby Kapolei, known as Oahu’s “Second City.”

Found on the 11th floor of the desirable Ocean Tower complex, the apartment can easily accommodate a group of 4 with two bedrooms and two bathrooms. Four pristine beaches and lagoons are found just steps away from your door, offering a safe and secluded setting for guests to swim, snorkel, sunbathe, build sand castles, walk, run or simply nap. This comfortable and upscale beachside vacation home in Oahu can be yours for around $520 a night.

3. Open, Loft-Like Retreat On Oahu’s Laie Point Peninsula

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Laie Point in north Oahu is a place of exceptional beauty, where a rugged, lava rock coastline gives way to pristine, sandy beaches. This spectacular oceanfront VRBO in Oahu will simply take your breath away! The vaulted ceilings and soaring windows create an open, loft-like feel, flooding the space with tons of natural light and perfectly showcasing the fantastic ocean views.

With six big bedrooms, 4.5 bathrooms, and multiple spaces to entertain or lounge, this spectacular home can comfortably accommodate up to 16 guests. With so much room to spread out, this glamorous home is ideal for multiple families or a big group of friends who want to relax together but retreat to their own private space. This 4,500 sq.ft. Oahu vacation rental can be yours from around $700 a night.

2. Luxurious, Cape Cod-Style Lanikai Oceanfront Home

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This exceptional property is perfectly positioned between two of the most desirable beaches in the world, Lanikai and Kailua. Flanked on either side by their pristine, white sands, this luxury oceanfront Cape Cod-style Oahu vacation home boasts incredible ocean views for around $750 a night. With two bedrooms and 2.5 baths, this is certainly one of the best Oahu VRBO homes for a small family or two couples traveling to Hawaii together.

The surrounding Kailua area attracts notable figures like Barack Obama and actress Michelle Pfieffer, in addition to Hawaiians seeking a vacation of their own. The home itself has everything you need to relax in style or entertain in total privacy, with a huge living space, a gourmet kitchen with eat-in island, and a large porch overlooking the bright blue ocean.

1. The Ultimate Zen-Like Luxury Retreat On Oahu’s Kaneohe Bay

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Escape the hustle and bustle of daily life at this contemporary luxury home on Kaneohe Bay in east Oahu. Find your inner Zen together, embracing the stunning natural surroundings including breathtaking mountain and ocean views from throughout the home. With five bedrooms and four bathrooms, the home can easily accommodate from 8-14 guests, ideal for pre-wedding events, a memorable family reunion, or a relaxing group retreat.

The private outdoor spaces are perfect for entertaining, with a huge heated swimming pool, 12-person jetted spa, and fire pit lounge, all overlooking the peaceful bay and lush mountains in the distance. Inside, the decor is sleek and contemporary, including a gourmet kitchen with top-of-the-line Subzero, Miele, Grohe, and Bosch appliances. All of the living spaces have been designed to maximize comfort while keeping the focus on the property’s fantastic views. This spectacular luxury home can be yours for around $1,195 a night.

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