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Top 10 Oahu Luxury Vacation Rentals

Experience a true island retreat with the best Oahu luxury vacation homes. Villas, beach houses, and condos offer stunning views of the sun setting over Waikiki Beach or stunning ocean views from Lanikai’s private white sandy beach. When only the best in Oahu will do, book directly with the Property Manager for each Oahu luxury vacation home. Our list is compiled from our experience staying at many of these homes. For over 20 years we have been in the Oahu luxury vacation rental business. When you’re ready for your next Oahu vacation take a minute to look at the best luxury vacation rental homes and what they have to offer. Stay where the elites have stayed, from the Obama luxury home to Oahu rentals featured in your favorite blockbuster movies. Our list covers all the best Oahu luxury rentals.

beach front and mountain view from Kainani Estate Hawaii luxury resort
Average $11,000/night

Kainani Estate

Honolulu, Hawaii

Welcome to Kainani Estate, a spacious beachfront paradise with lush tropical grounds, private tennis court, two swimming pools, Jacuzzi, and luxurious accommodations, perfect for large families or corporate retreats in the heart of Oahu…

8 Beds

7 Baths

7 Bedrooms

Banyan Ohana Vacation Rental on Oahu
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

Kahala Hale Vacation Rental on Oahu
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

lounge area and ocean view at Nalu Lani Villa in Oahu Hawaii
Average $10,000/night

Nalu Lani Villa

Kailua, Hawaii

Discover the epitome of relaxation at Nalu Lani Villa, a luxurious 3-bedroom, 4-bathroom hillside retreat in Lanikai, offering breathtaking ocean views, a solar-heated pool, and chic modern furnishings for an unforgettable Oahu getaway…

4 Beds

4 Baths

3 Bedrooms

Waimanalo Hale Vacation Rental on Oahu
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

One Kea Estate Vacation Rental on Oahu
Average $8,286/night

One Kea Estate

Honolulu, Hawaii

Oahu’s Newest Luxury Estate Ocean 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

pool view at Hoku Lele Resort on Oauha
Average $8,282/night

Hoku Lele Resort

Honolulu, Hawaii

Welcome to Hoku Lele Resort, your perfect getaway on Waikiki Beach, offering luxurious accommodations, a resort pool with private cabanas, live entertainment, a fitness center, day spa, and a children’s program for an unforgettable vacation.

3 Beds

3 Baths

3 Bedrooms

White Hale Vacation Rental on Oahu
Average $7,070/night

White Hale

Hawaii Kai, Hawaii

Welcome Home to ‘White Hale! Are you ready for a truly private and awe-inspiring waterfront vacation? This oceanfront estate designed by Philip ‘Pip’ White, offers sunsets and views galore! All while being centrally located 10 minutes to Kahala and 5 minutes…

9 Beds

6 Baths

5 Bedrooms

tropical and pool view at Lani Moana Villas Hawaii luxury
Average $6,970/night

Lani Moana Villas

Kahuku, Hawaii

Welcome Lani Moana Villas at Turtle Bay, a luxurious beachside retreat offering stunning ocean views, direct access to the beach, pool, and BBQs, and a range of resort amenities for an unforgettable family vacation or romantic escape…

8 Beds

3 Baths

4 Bedrooms

Moanas Edge Vacation Rental on Oahu
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

All about Oahu

Oahu, known as the “Gathering Place”, is the most popular Hawaiian Island destination as it has incredible beauty, history, culture, cuisine, and activities. Oahu has some of the most amazing Oahu luxury home rentals!

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. In addition, 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).

Things to do

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. Plenty of Oahu luxury vacation homes and rentals are nearby Hanauma Bay.

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. With so many Oahu luxury vacation homes in Waikiki to choose from on our list, it’s easy to find the perfect home.

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