Hawaii’s Most Luxurious Vacations Rentals
Sorted by most expensive per night and grouped by island.
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Kauai:
1. Hanalei Kuono
Hanalei, Hawaii
Situated on over an acre of beachfront land, directly in the center of Hanalei Bay is this well-appointed five-bedroom gated estate, perfect for corporate retreats, extended families, or anyone else requiring privacy in the ultimate setting…
5 Beds
4 Baths
5 Bedrooms
2. Oioina Estate
Kalihiwai, Hawaii
Between the mystical mountains and renowned Secret Beach, The Dali Hale Estate is more than a home: you’ll feel the magic the moment you arrive. With more than 500 feet of ocean frontage, the Dali Hale is the perfect place to gather for grand family reunions…
8 Beds
8 Baths
8 Bedrooms
3. Lagoon Resort
Lihue, Hawaii
Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing our rates to direct resort bookings. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using their…
3 Beds
2 Baths
2 Bedrooms
4. Poipu Beach Hale
Koloa, Hawaii
An irresistible fusion of glamorous seaside resort and casually elegant, island-style private home, Waiohai Beach House offers the best of both worlds and more. The spacious, beautifully furnished 4BR/4BA villa (the only single-family vacation rental on Poipu Beach)…
4 Beds
4 Baths
4 Bedrooms
5. Heavenly Ohana
Hanalei, Hawaii
Located beachfront on the enchanting Hanalei Bay, Lani Kai (“Heavenly Ocean Home”) is a newly remodeled four bedroom, three bathroom home ideal for a large family or couples traveling together wanting some well-deserved space. Recent renovations include…
4 Beds
3 Baths
4 Bedrooms
6. Pali Kai
Lihue, Hawaii
The pristine ambiance of the Pali Kai Palace is accentuated by its extraordinary vista. Perched upon the Kalapaki Cliffs, this unique location in Lihue offers sensational views of the ocean, mountains, and harbor. With intentional interior designing and custom…
8 Beds
7 Baths
7 Bedrooms
7. Haena Beach House
Haena, Hawaii
Haena Beach House offers a once-in-a-lifetime vacation experience, providing contemporary luxury in a private beachfront setting. Ideal for large groups, the home showcases breathtaking panoramic views of the Pacific from its living spaces and each of its bedrooms…
6 Beds
5 Baths
5 Bedrooms
8. Hale Mana
Kalihiwai, Hawaii
Welcome to Hale Mana, one of Kauai’s most beautiful island treasures. This stunning three-acre private estate will bathe you in every luxury with its beautifully appointed amenities, secluded beach, and tremendous ocean views. If you are looking for Hawaii’s best…
11 Beds
6 Baths
5 Bedrooms
9. Dolphin House
Hanalei, Hawaii
Renovated and expanded in July 2011 to include 7 bedrooms! Hanalei’s classic property sits on over one acre of land. The largest oceanfront rental property in Hanalei Bay! The residence and guesthouse have been upgraded throughout. New finishes include…
8 Beds
7 Baths
6 Bedrooms
10. Kumu Home
Lihue, Hawaii
Timbers Kauai – Ocean Club and Residences is a residential enclave located on the ocean*s edge of the Pacific. All of Timbers* signature amenities are here; such as two pools to fit whatever mood you are in – a serene two-tiered infinity pool overlooking…
4 Beds
3 Baths
3 Bedrooms
11. Nanini Hale
Lihue, Hawaii
This private residence has an expansive floor plan and spacious lanais. Enjoy the sunrise over the Pacific Ocean and eastern views of the resort and the Nanini Point lighthouse. The split-level floor plan provides space for everyone to relax. The floor-to-ceiling…
2 Beds
1 Bath
5 Bedrooms
12. Hanalei Cottage
Hanalei, Hawaii
Located on Kauai’s beautiful north shore, this beachfront home is surrounded by lush, tropical foliage. Enjoy a spacious living room upstairs as well as a comfortable family room downstairs. The upstairs balcony features magnificent views of Hanalei Bay which is just…
4 Beds
4 Baths
3 Bedrooms