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Oahu

20 of Oahu’s most luxurious vacation rentals

Sorted by most expensive per night.

Waikiki Kaona Vacation Rental on Oahu
Average $15,291/night

1. 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

Kailua Cabana Vacation Rental on Oahu
Average $11,000/night

2. 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

Banyan Ohana Vacation Rental on Oahu
Average $10,893/night

3. 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

4. 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

Kailua Kahakai Vacation Rental on Oahu
Average $10,000/night

5. 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

Waimanalo Hale Vacation Rental on Oahu
Average $10,000/night

6. 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

7. 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

Kai Moena Vacation Rental on Oahu
Average $8,282/night

8. Kai Moena

Kailua, Hawaii

This luxury vacation rental sits on nearly 60,000 sq. ft. of prime Kailua Beach property with 225+ sq. ft. of linear beach frontage featuring soft sand, blue water, and spectacular views of Kailua Bay. Two separate rental houses by award-winning architect James McPeak…

10 Beds

8 Baths

9 Bedrooms

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

9. 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

Pipeline Hale Vacation Rental on Oahu
Average $6,970/night

10. 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

Moanas Edge Vacation Rental on Oahu
Average $6,400/night

11. 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

Waikiki Ikena Vacation Rental on Oahu
Average $6,339/night

12. 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

Kea Moana Vacation Rental on Oahu
Average $5,500/night

13. 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

Infinity Hale Vacation Rental on Oahu
Average $5,250/night

14. Infinity Hale

Honolulu, Hawaii

Experience the beauty and charm of Infinity Hale (Endless Family House)-The North Shore of Oahu’s Private Luxury Villa. This hidden gem sits on an acre of amazing oceanfront land. Want a high-end home with multi-million dollar views of the world-renowned…

7 Beds

7 Baths

6 Bedrooms

Kahala Bridge Estate Vacation Rental on Oahu
Average $4,427/night

15. Kahala Bridge Estate

Kahala, Hawaii

This spacious beachfront estate is situated on lush tropical grounds, nestled in between palm trees. Enter the grounds thru the privacy gate to enjoy two swimming pools, Jacuzzi, waterfalls, and your private tennis court. Cottage Pool Heated…

8 Beds

7 Baths

7 Bedrooms

Moana kiʻi kiʻi Vacation Rental on Oahu
Average $4,000/night

16. Moana kiʻi kiʻi

Kahala, Hawaii

This oceanfront crown jewel – a modern diamond head home – offers a penthouse atmosphere for entertaining or quiet days watching ocean waves. This is a truly one-of-a-kind property with beach access. Located very near the Doris Duke “Shangri La,” this executive home…

5 Beds

5 Baths

4 Bedrooms

Kai Valhalla Vacation Rental on Oahu
Average $3,716/night

17. 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

Koa Loft Vacation Rental on Oahu
Average $3,250/night

18. Koa Loft

Lanikai, Hawaii

Koa Loft – This four-bedroom, four-bathroom home is ideal for families. It features high vaulted ceilings, a large open living space, plenty of dining areas, a perfectly manicured yard, and access to a gorgeous white sand beach just yards away…

6 Beds

4 Baths

4 Bedrooms

Seaside Villa Vacation Rental on Oahu
Average $3,034/night

19. Seaside Villa

Kahala, Hawaii

Your very own oceanfront oasis awaits you at Seaside Villa, a premier 4 bedroom and 4 bathroom estate residing on the cliffs of scenic Oahu. When you traverse through the doors of this Balinese-inspired vacation rental, you’ll step into a paradise that features…

4 Beds

4 Baths

4 Bedrooms

Mokulua Moana Vacation Rental on Oahu
Average $2,435/night

20. Mokulua Moana

Lanikai, Hawaii

Mokulua Moana is a lovely beach home located on a pristine, secluded white sand beach that can only be accessed by a few houses on the property, or by boat. Everywhere you look is the sparkling ocean. Wake up each morning to a glorious sunrise to start your day…

6 Beds

9 Baths

6 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.

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).

Places

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.

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.