Hawaii’s Most Luxurious Vacations Rentals
Sorted by most expensive per night and grouped by island.
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Oahu:
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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