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Oahu

12 of Oahu’s most luxurious vacation rentals

Sorted by most expensive per night.

Average $15,291/night

Waikiki Kaona

Waikiki, Hawaii

Wake up in the heart of Waikiki at a fully furnished 1,700 square foot penthouse condo designed to satisfy your every need & desire. You won’t find anything like this similar in all of Waikiki. This “Close to Everything with Everything” & all the bells and whistles listing…

10 Beds

2 Baths

3 Bedrooms

Average $11,000/night

Kailua Cabana

Kailua, Hawaii

Relax and unwind at this stunning estate with direct access to the beautiful sandy beaches of Kailua. This exquisite 5 bedroom main residence offers 11,000+ sq ft of lavish living plus a gorgeous separate 3 bedroom guest house. Incredible details, expert craftsmanship…

8 Beds

8 Baths

8 Bedrooms

Average $10,893/night

Banyan Ohana

Kahala, Hawaii

Banyan Ohana is Oahu’s most luxurious vacation rental near the foot of Diamond Head. The exquisite home features seven bedrooms, eight full baths, and a half-bath, encompassing 14,000 square feet all within a private beachfront estate. This stylish and…

8 Beds

9 Baths

8 Bedrooms

Average $10,700/night

Kahala Hale

Honolulu, Hawaii

Boasting an extraordinary beachfront location, this private Kahala vacation rental estate provides all the modern luxury features your large group requires, with the charm of old Hawaii. Kahala Beachside Estate offers direct beach access, its own pool, and spa, seven…

14 Beds

8 Baths

7 Bedrooms

Average $10,000/night

Kailua Kahakai

Kailua, Hawaii

These two magnificent homes both sleep 12 people (24 total) is nestled on two acres of land, that has its own shared swimming pool and hot tub, and the most beautiful sandy beach imaginable at your doorstep. It is completely furnished and beautifully maintained…

12 Beds

12 Baths

12 Bedrooms

Average $10,000/night

Waimanalo Hale

Waimanalo, Hawaii

Experience Hawaii in an exquisite beachfront mansion with panoramic ocean views on beautiful Waimanalo Beach (famous filming locale for Magnum P.I., Hawaii 5-0, & Lost). Waimanalo’s small town doesn’t allow hotels, making it the perfect getaway from the…

10 Beds

8 Baths

9 Bedrooms

Average $8,286/night

One Kea Estate

Honolulu, Hawaii

Oahu’s Newest Luxury EstateOcean House is the newest residence in the collection of ultra-luxury homes designed by renowned Hawaii Architect Jim McPeak and built by San Diego based developer Mark Gosselin. This estate is a modern take on Oahu’s well-known…

6 Beds

7 Baths

6 Bedrooms

Average $6,970/night

Pipeline Hale

Pupukea, Hawaii

The Pipeline Manor is a spectacular example of modern island style. Unparalleled ocean views are available from multiple locations in the home bringing in the sights and smells of the Pacific. Other features include HDTV, gourmet kitchen, off-street parking…

5 Beds

4 Baths

5 Bedrooms

Average $6,400/night

Moanas Edge

Honolulu, Hawaii

The Jewel of Waikiki challenges traditional luxury with nine multi-room suites, each occupying an entire floor and offering complete privacy. The experience is enhanced with butler service, ensuring all requests are addressed promptly and discretely through…

3 Beds

4 Baths

4 Bedrooms

Average $6,339/night

Waikiki Ikena

Waikiki, Hawaii

Located in the rapidly growing urban neighborhood of Kaka’ako on the south shore of O’ahu, Hokua Grand Penthouse sits at the top of the luxury Hokua condominium, just across the street from Ala Moana Beach Park. With sensational ocean and city views…

4 Beds

4 Baths

3 Bedrooms

Average $5,500/night

Kea Moana

Lanikai, Hawaii

This gorgeous 5 bedroom, 4.5 bathroom, the gated oceanfront villa was built in 1918 and has just been fully remodeled with an open, contemporary beach house feel while still honoring the original architecture of the home. In the renovation we revealed beautiful…

7 Beds

5 Baths

5 Bedrooms

Average $3,716/night

Kai Valhalla

Lanikai, Hawaii

With a private, gated entrance and a sophisticated and luxurious feel throughout, Kai Valhalla is the indulgence you need on your next Hawaiian vacation. This larger-than-life custom-built five-bedroom, four-and-a-half-bath home spread out over three stories is ideal…

6 Beds

5 Baths

5 Bedrooms

Oahu, known as the “Gathering Place”, is the most popular Hawaiian Island destination as it has incredible beauty, history, culture, cuisine, and activities.

Check out the world-famous north shore surf breaks of Banzai Pipeline, Haleiwa, Waimea Bay, and Sunset Beach along with the “seven-mile miracle”.  The north shore has the beautiful and rustic surf town of Haleiwa, a fun bike path, and many spots made famous over the years from TV and movie shoots. Don’t miss grabbing some local grinds at the food trucks and you might also think about playing a round of golf at the Turtle Bay Resort.  Turtle Bay also has one of the few beachfront restaurants and bars on Oahu and is worth checking out (Roy’s Beach House and the Point).

The towns of Kailua, Kaneohe, and Waimanalo on the windward side of the island have some of the most incredible beaches in all of Hawaii perfect for kayaking, windsurfing, and bodysurfing.  The white sand and turquoise waters of the Lanikai neighborhood are world-famous as is the incredible view of the offshore Mokulua Islands. Adventurous folks can rent a kayak or stand-up paddleboard to gain access to the small beach on the northernmost Mok called Moku Nui.

Ask your host about their favorite restaurant or nightlife hot spot in downtown Honolulu and Waikiki, advice on how to best see historic Pearl Harbor, where to take in a local show, or when to go to the local farmers’ market (offering some great organic choices).

Go snorkeling at Hanauma Bay and see incredible fish and coral while swimming in a dormant volcanic crater and consider checking out the dangerous shore break and brave bodyboarders at nearby Sandy’s beach.

Consider heading over to the Ko Olina Resort area to see Disney’s Aulani resort and or taking the scenic H2 highway up to the north shore or the H3 highway through the Ko’olau Mountains on what some consider to be the most beautiful highway in the world.

Some think that Oahu and Waikiki beach started off the American craze of spending their vacation time traveling to far-flung exotic places.  Once you visit Oahu and see things for yourself, you might understand why it all started here.