Hawaii’s Most Luxurious Vacations Rentals
Sorted by most expensive per night and grouped by island.
Jump to:
Big Island
1. Fairways North 1
Mauna Kea Resort, Hawaii
Nestled in seclusion on an acre of land in the exclusive Mauna Kea Resort, this five-bedroom, seven-bath estate home represents the epitome of luxury, leisure, and ease. Fairways North #1, ideal for families or groups of friends, consists of three pod-style…
4 Beds
3 Baths
3 Bedrooms
2. Blue Lagoon
Puako, Hawaii
Enjoy the best Hawaii has to offer in this luxury 10,000 sq ft tropical estate. It includes a private heated pool/spa and includes access to Mauna Lani resort area amenities including a private beach and beach club(included with rental), tennis, and fitness…
4 Beds
4 Baths
3 Bedrooms
3. Beach House at the Bluffs
Mauna Kea Resort, Hawaii
Built in 2008 by architect Roth Kimura, this two-story, 8,000 square foot luxury estate home with 2,750 square feet of outdoor entertaining space is located on a private, secure cul-de-sac in the Bluffs area of the Kohala Coast. The Beach House at the Bluffs…
6 Beds
7 Bath
4 Bedrooms
4. 106 Pu’u Kole
Kaupulehu, Hawaii
This resort home cradles its guests in the lap of sumptuous serenity. Situated on a premier private corner lot overlooking the 13th green of the exclusive Ke‘olu golf course, this home boasts over 4,200 square feet of interior living space and 1,500 square feet…
5 Beds
5 Baths
4 Bedrooms
5. Kulanakauhale 3558
Kailua-Kona, Hawaii
Set on a bluff in the newest residential community at the exclusive Four Seasons Resort Hualalai, this luxury ocean-view estate home provides the ideal setting for a family or friend’s getaway to paradise. The home boasts over 3,460 square feet of interior space…
4 Beds
5 Baths
4 Bedrooms
6. Pauoa Enclave
Puako, Hawaii
Located in a prime position, within the gated, luxury enclave of Pauoa Beach, in the Big Island’s Mauna Lani Resort, the Pauoa Beach Oceanfront Villa delivers a 5-star vacation rental experience. Travelers seeking elegant surroundings, access to private clubs…
5 Beds
4 Bath
4 Bedrooms
7. Seaside Estate
Holualoa, Hawaii
Transcend paradise with our absolute oceanfront 3 story 5 bedroom home located only blocks from Kailua-Kona town and within a guarded gate community of luxury estates. Your private oceanfront setting overlooks rich lava, white sands, crashing waves, and Hawaii’s…
5 Beds
7 Baths
5 Bedrooms
8. Laueki Estate
Kaupulehu, Hawaii
Centrally located in this tranquil and rejuvenating oceanside retreat, Lalani Lau’eki is a private oasis nestled between the exquisite and expansive ocean and mountain views. Just a short golf cart ride away is everything the premier resort offers such as world…
4 Beds
5 Baths
4 Bedrooms
9. Pakui Retreat
Kaupulehu, Hawaii
Welcome to your very own corner of paradise at Hualalai Four Seasons Resort! This estate is your perfect home-away-from-home. Highlighting Hawaii’s natural beauty with indoor-outdoor living, the Pakui Retreat estate features exquisite interior ambiance…
5 Beds
4 Bath
3 Bedrooms
10. Pauoa Beach Villa
Puako, Hawaii
Pauoa Beach Estate has been meticulously cared for, and designed specifically to live life relaxed while enjoying designer furnishings and elegant island sophistication. Exquisite and rich Koa and Sapele wood millwork pays homage to the home’s location…
5 Beds
6 Baths
4 Bedrooms