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Pools, Views and Privacy
Oahu luxury vacation rentals include private homes, ocean-view villas, beachfront estates and upscale retreats near Waikiki, Kahala, Ko Olina, Kailua and the North Shore. Choose extra space, privacy, pools and island views.
Featured Luxury Rentals
Start with private homes and oceanfront estates chosen for a higher-end Hawaii stay.
From $10,809/night
Royal Hawaiian Estate is an extraordinary 9-bedroom oceanfront vacation rental on Oahu's scenic east shore in Waimanalo, blending luxury, privacy,...
From $3,093/night
Walker's Lanikai Beach House is a historic oceanfront retreat on one of Oahu's most beautiful beaches. Originally built in 1934 by Queen...
From $1,798/night
This Kailua Beachfront Home is a relaxed oceanfront retreat offering panoramic views of Kailua Bay and the Ko'olau Mountains. Located just minutes...
From $2,211/night
Kai Aniani or "Sea of Glass" is a modern beachfront vacation rental on Oahu's North Shore, offering architectural elegance, sweeping ocean views, and...
From $2,090/night
Moani Kaiolohia is a spacious 6-bedroom, 4-bath Kahuku vacation home set on a private acre with direct beach access, perfect for large families or...
From $2,200/night
Hale Makai at Diamond Head is a luxury oceanfront retreat on Oahu's prestigious Gold Coast, just minutes from Waikiki and framed by stunning views of...
From $2,250/night
Hale Lanikai is a newly remodeled beachfront vacation rental offering classic Hawaiian charm with modern comforts, located on the soft sands of...
From $1,714/night
The Sunset Beach House is a Polynesian-style beachfront vacation home located directly on the sands of Oahu's iconic Sunset Beach. This 4-bedroom,...
From $2,593/night
This Kailua Beachfront Estate is a beautifully renovated 6-bedroom vacation rental set directly on the soft white sands of Oahu's renowned Kailua...
From $1,260/night
Laniakea Beach House is a beachfront vacation home on Oahu's North Shore, set directly along the famous sea turtle haven of Laniakea Beach. With 4...
From $5,803/night
The Kahala Beachfront Estate is a luxury 7-bedroom vacation home nestled on tropical grounds along prestigious Kahala Beach. This spacious Kahala...
From $785/night
This Waialua Oceanfront Retreat is a beautifully furnished 4-bedroom vacation home featuring two luxurious master suites, two oceanfront living...
From $10,328/night
Sea Cliff Chic is an architectural masterpiece perched above Oahu's Portlock coastline, offering sweeping ocean views, an infinity-edge pool, and...
From $3,221/night
Hale Lani is a serene hillside retreat overlooking Lanikai Beach, offering panoramic views of the Pacific and Mokulua Islands. This 3-bedroom, 4-bath...
From $2,418/night
Niu Beach Estate is a newly remodeled 5-bedroom luxury vacation home on Oahu's south shore, nestled between Waikiki and Hawaii Kai. This expansive...
From $4,149/night
Lanikai Hillside Estate is a stunning 7-bedroom luxury vacation home perched above the turquoise shores of Lanikai, offering over 8,400 sq. ft. of...
From $2,022/night
This Lanikai Oceanfront Home is a luxurious retreat blending old Hawaii charm with modern comfort, featuring spacious concrete-floored interiors,...
From $1,018/night
Lanikai Breeze is a stylish 5-bedroom vacation rental just steps from the powdery sands of Lanikai Beach, offering a perfect blend of luxury and...
From $1,902/night
Majestic Mahakea is a luxury oceanfront retreat in Laie on Oahu's northeastern shore, offering direct access to a private ½-mile stretch of Mahakea...
From $6,311/night
Kahala Beachside Estate is a grand 7-bedroom, 8-bath luxury oceanfront vacation rental in one of Oahu's most prestigious neighborhoods. With a...
From $2,242/night
Kailua Beach Villa is a spacious 5-bedroom luxury vacation rental set directly on the sands of Oahu's beautiful east shore. With expansive ocean...
From $5,177/night
The Kahala Mansion is Honolulu's premier luxury estate, offering refined elegance, privacy, and event-ready grandeur just steps from the beach. Ideal...
From $2,179/night
Waialua Beachfront Estate is a luxurious oceanfront vacation rental on Oahu's North Shore, offering direct beach access, a private pool, and flexible...
From $2,917/night
Ocean Villa Emilie is a sleek, architect-designed luxury estate in Honolulu, blending modern elegance with panoramic ocean and mountain views. This...
From $4,217/night
Kahala Oceanside is a luxurious 6-bedroom oceanfront vacation rental on Oahu's prestigious Kahala Avenue, designed to accommodate up to 14 guests in...
From $2,450/night
Set on nearly an acre of prime Kailua Beach frontage, this newly refurbished 3-bedroom, 3-bath home features a large private swimming pool, flexible...
More Luxury Stays
See more high-end homes from the same collection in a simple, easy-to-scan layout.
Naupaka Hale - Lanikai Beach Home & Cottage
Surfer's Paradise - Beachfront Vacation Rental on Oahu's North Shore
Kailua Beach Historic Renovated Cottage
Hale Kolea - Luxury Lanikai Hillside Retreat
Mokulua Sunrise Ocean Villa Lanikai
Lanikai Oceanfront Home with Pool and Japanese-Style Hot Tub
Lulani House Beachfront Vacation Home in Haleiwa
Rocky Point Hale Luxury Oceanfront Vacation Home in Haleiwa
Luxury Beach Vacation House in Kailua Beach
Oceanfront Lanikai Beach Vacation Home
Hale Kalea - Oceanfront Vacation Rental on the North Shore of Oahu
Place in Paradise - Kailua Beach Oceanfront Vacation Home
Palione Papalani - Tropical Estate with Lagoon Pool on Kailua Beach
Samurai House - Japanese-Inspired Luxury Estate on Oahu's North Shore
Kailua Luxury Beachfront House
Pili Pono: Elegant Honolulu Retreat with Pool & Private Oasis