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Villas in Oahu

Oahu Villa Rentals (Hawaii)

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Aina Haina

Aina Haina, Oahu, Hawaii
5 br, 5.5 ba (5 Ensuite)

Get away from it all at Moana Lani, a private, luxurious 5-bedroom home set along Oahu’s majestic south coast. Oahu is the heart of the Hawaiian islands and a natural gathering point for its people; an ideal embraced by the villa’s communal feel, spacious grounds and active outlook.

From
US$2650 - 4500 /nt

View Villa Moana Lani
Aina Haina, Oahu, Hawaii
4 br, 3 ba (2 Ensuite)

Tropical resplendence soars to new heights at Oceanside Paradise in Oahu, Hawaii—a surfer’s paradise! This residence is a perfect choice for guests seeking hotel-like amenities, ultimate privacy and an epic spot just steps away to carve waves. Relax and rejuvenate at this elegant beachside luxury getaway located in the exclusive Wailupe Peninsula.

From
US$1075 - 2266 /nt

View Villa Oceanside Paradise

Diamond Head

Diamond Head, Oahu, Hawaii
4 br, 4.5 ba (4 Ensuite)

Typically reserved for celebrities and the jet setting elite, Empress at Diamond Head is a beachfront luxury villa located on the slopes of the Diamond Head volcano on the island of Oahu in the great state of Hawaii. The property around this four-bedroom villa is littered with swaying royal palm trees and can generously accommodate up to eight travelers.

From
US$4500 - 6250 /nt

View Villa Empress at Diamond Head
Diamond Head, Oahu, Hawaii
4 br, 5.5 ba (4 Ensuite)

Situated on the island of Oahu’s stunningly beautiful Gold Coast, Diamond Head Villa is a magnificent four-bedroom luxury home with room for ten guests. So named for its close proximity to the dormant Diamond Head volcano, the villa is only a short drive from beautiful downtown Honolulu, Hawaii’s bustling metropolis.

From
US$3000 - 5500 /nt

View Villa Diamond Head Villa
Diamond Head, Oahu, Hawaii
4 br, 4.5 ba (4 Ensuite)

Kalakaua Villa is located along the oceanfront in the exclusive Diamond Head area of Oahu. Rising from the lush green landscaping with plenty of floor-to-ceiling windows, this private vacation rental in Hawaii offers a chance for friends and families to unwind in Pacific paradise.

From
US$1950 - 3500 /nt

View Villa Kalakaua Villa
Diamond Head, Oahu, Hawaii
3 br, 3.5 ba (3 Ensuite)

A captivating oceanfront property that literally borders the lip of the Southern Pacific, Diamond Head Tiki Estate is a place where dreams come true. Located on the southern shore of Hawaii’s Oahu island, in the environs of the dormant volcano known as Diamond Head, this three-bedroom property for up to seven guests sets the standard for tropical luxury real estate.

From
US$1250 - 3215 /nt

View Villa Diamond Head Tiki Estate
Diamond Head, Oahu, Hawaii
4 br, 4 ba (3 Ensuite)

A Hawaiian beachfront property overlooking Oahu’s famed Gold Coast, Diamond Head Hawaii Lani is an opulent estate with gorgeous panoramic ocean views tucked away near a dormant volcano that is one of the island’s most esteemed landmarks. This four-bedroom luxury home was renovated recently and can comfortably host up to eight lucky guests.

From
US$803 - 2875 /nt

View Villa Diamond Head Hawaii Lani
Diamond Head, Oahu, Hawaii
5 br, 6 ba

Gail Street Villa is situated in the exclusive Diamond Head area of Oahu. Rising from the lush green landscaping with plenty of floor-to-ceiling windows, this private vacation rental in Hawaii offers an opportunity for friends and families to unwind in Pacific paradise.

From
US$1750 - 2800 /nt

View Villa Gail Street Villa
Diamond Head, Oahu, Hawaii
3 br, 2 ba (1 Ensuite)

It may be inspired by the architecture of Indonesia, but the charm of Bali Estate is all Hawaiian. Nestled into the slope of Diamond Head just a few miles from Waikiki Beach and minutes from shopping and dining, the villa enchants with lush landscaping, rooms that open to the tradewinds and views of the sea in the distance.

From
US$2000 - 2500 /nt

View Villa Bali Estate
Diamond Head, Oahu, Hawaii
3 br, 2 ba, Pool

Enjoy the same spectacular views as heiress Doris Duke at Seaside Hideaway. Set near Duke’s Shangri La between Waikiki and Kahala, the secluded villa overlooks some of the best surfing spots on Oahu’s South Shore.

From
US$1750 - 2500 /nt

View Villa Seaside Hideaway
Diamond Head, Oahu, Hawaii
4 br, 3.5 ba (2 Ensuite)

Seated along a winding, private drive perched on the slopes of Diamond Head, Wailele Villa boasts a breathtaking 180 degree view of Oahu’s southern shore. A modern Hawaiian paradise, Wailele Villa is the perfect combination of proximity and privacy: a short ten minute walk from the beach, and only a few miles from all the excitement of Waikiki.

From
US$1245 - 2500 /nt

View Villa Wailele Villa
Diamond Head, Oahu, Hawaii
4 br, 3 ba (2 Ensuite)

If you’re looking for a lush, private getaway just minutes from the beach, golf and Waikiki, make Hale Kulamanu your home away from home. Tucked into a garden with views of the ocean and Diamond Head, the property is an oasis with a generous outdoor living area and charming, comfortable interiors.

From
US$1250 - 2000 /nt

View Villa Hale Kulamanu

Hawaii Kai

Hawaii Kai, Oahu, Hawaii
5 br, 5.5 ba (4 Ensuite)

Once owned by country music superstar Dolly Parton, Banyan Tree Beach Estate is a massive luxury villa situated in Hawaii Kai, on the island of Oahu. This five-bedroom oceanfront estate sits on half an acre and is comprised of both a large stately main house and an opulent adjacent guest house.

From
US$2750 - 3200 /nt

View Villa Banyan Tree Beach Estate
Hawaii Kai, Oahu, Hawaii
5 br, 4.5 ba

Welcome to Nani Wai, a private Luxury Vacation retreat that is all your own. Once you step inside the gate of this beautiful marina front home, you will feel as if you have literally stepped into your own private compound - an island paradise just for you and your loved ones! With 5 bedrooms, 4 baths, a built in bunk bed AND sleeper sofa, this open-concept floor plan with soaring ceilings and large rooms has plenty of places for everyone to flow.

From
US$875 - 1875 /nt

View Villa Nani Wai

Honolulu

Honolulu, Oahu, Hawaii
5 br, 4 ba (3 Ensuite)

Nestled in the exclusive and upscale Kahala area on Oahu’s south shore, Kahala Lani is the ultimate golfer’s paradise! Just outside your front door is the championship golf course at Waialae Country Club, and you will also get to enjoy your very own putting green in the backyard. A gated rock wall provides security and privacy around this nearly 20,000 square foot tropical Hawaiian oasis that sits close to the ocean.

From
US$1250 - 18850 /nt

View Villa Kahala Lani
Honolulu, Oahu, Hawaii
8 br, 8.5 ba (8 Ensuite)

Banyan House is Oahu’s finest luxury beach estate. It was built specifically to provide the most luxurious accommodations in Hawaii.

From
US$6000 - 10500 /nt

View Villa Banyan House
Honolulu, Oahu, Hawaii
4 br, 5 ba (4 Ensuite)

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From
US$1000 - 3400 /nt

View Villa Honolulu Sky Villa

Kahala

Kahala, Oahu, Hawaii
4 br, 4.5 ba

Kaikuono Villa is an oceanfront luxury residence in Oahu sure to take your breath away. Located in the exclusive Kahala area of Honolulu, this vacation rental offers contemporary sophistication just minutes from Waikiki, the Diamond Head Lookout and Ala Moana Shopping Center.

From
US$4000 - 7000 /nt

View Villa Kaikuono Villa
Kahala, Oahu, Hawaii
7 br, 6.5 ba (3 Ensuite)

Instead of staying at a crowded resort during your trip to Hawaii, wouldn’t it better if you had the entire resort to yourself? That’s what Kahala Mini Resort offers Oahu-bound travelers – a massive tropical estate with seven rooms and space for up to fourteen guests, with resort-grade amenities and plenty of first class features. Placed right on the sands of Kahala Beach with tall royal palms that encircle the whole of the estate, every guest staying here will feel like a chief.

From
US$4000 - 4600 /nt

View Villa Kahala Mini Resort
Kahala, Oahu, Hawaii
4 br, 4.5 ba (4 Ensuite)

Built on the shores of Oahu, beachfront Kalani Villa has four bedrooms and four ensuite bathrooms, and is one of our most family-friendly villas in Hawaii. Pretty and polished, this buttercream-yellow plantation-style villa is fronted by a curved pool with views of the Pacific Ocean waves beyond.

From
US$1750 - 3125 /nt

View Villa Kalani Villa
Kahala, Oahu, Hawaii
4 br, 4.5 ba (4 Ensuite)

Situated on the eastern side of Diamond Head volcano in an area known as Kahala on the island of Oahu, is a luxury four-bedroom villa dubbed Tropical Oasis. This very accurately named Hawaiian home provides both comfort and privacy for groups no larger than eight, with many five-star amenities and proximity to notable sites, while at the same time occupying a relatively secluded location away from the city.

From
US$1500 - 2500 /nt

View Villa Tropical Oasis

Kailua

Kailua, Oahu, Hawaii
8 br, 8.5 ba (7 Ensuite)

Royal Kailua Estate is a veritable Polynesian palace of unrivaled opulence located in Kailua, on Oahu’s northern coast in the great state of Hawaii. The estate spans an astonishing 11,000 square feet atop a moderate inclination.

From
US$6000 - 12500 /nt

View Villa Royal Kailua Estate
Kailua, Oahu, Hawaii
5 br, 5 ba (4 Ensuite)

Discover a hidden Hawaii at Lanikai Hillside Estate. Part of an exclusive gated community, the villa, whose name means ‘heavenly sea,’ offers access to a semi-private beach and views of uninhabited islands off the coast.

From
US$6000 - 10000 /nt

View Villa Lanikai Hillside Estate
Kailua, Oahu, Hawaii
8 br, 8.5 ba (8 Ensuite)

Words simply cannot begin to describe the sheer magnificence of this massive eight bedroom property found in Kailua, in the Paradise of the Pacific, the great state of Hawaii. This eye-catching estate is like a small resort unto itself, with two large buildings and a gorgeous central swimming pool, panoramic views and elegant decor found in every corner.

From
US$6875 - 10000 /nt

View Villa Royal Beach Estate
Kailua, Oahu, Hawaii
6 br, 5.5 ba (3 Ensuite), Pool

Exquisite ultra luxury and unparalleled Kailua Beachfront Estate totaling nearly 60,000 sq ft with 255+ linear feet of beach frontage. Expansive tropical grounds, resort style pool/spa w/waterfalls, sauna, gym, tennis court with flood lights, hitting wall, marsh mellow BBQ, exterior BBQ area with bar, and more.

From
US$3125 - 7650 /nt

View Villa Bali Resort II
Kailua, Oahu, Hawaii
5 br, 5.5 ba (5 Ensuite)

Those who are familiar with Hawaiian history know that pineapples played a crucial role in the island’s development. The sweet fruit were grown out of large plantation estates, which serve as the inspiration for Plantation at Paradise Point whose lavish architecture is inspired in part by those same historical sites.

From
US$4500 - 6000 /nt

View Villa Plantation at Paradise Point
Kailua, Oahu, Hawaii
4 br, 3 ba

True to its name, Lanikai Seaside is a beautiful Hawaiian villa in a stunning oceanfront location. Set on the turquoise waters between Kailua Beach and Lanikai Beach, this luxury Oahu vacation rental has views both across the bay and out to the Pacific.

From
US$1500 - 5000 /nt

View Villa Lanikai Seaside
Kailua, Oahu, Hawaii
6 br, 7.5 ba (6 Ensuite), Pool

Construction Note: Please note that there is construction next door to this villa. Ohana Beach House will experience noise, depending on what work is being done at the time.

From
US$3000 - 5000 /nt

View Villa Ohana Beach House
Kailua, Oahu, Hawaii
5 br, 3.5 ba (2 Ensuite)

Kai Nani Villa is a delectable beachside home located on an exclusive street in Kailua, Hawaii. The tropical haven of Oahu island is known for its clear turquoise waters, Waikiki surfing and dreamlike golf courses.

From
US$3200 - 4000 /nt

View Villa Kai Nani Villa
Kailua, Oahu, Hawaii
3 br, 3 ba (3 Ensuite)

This stunning 3-bedroom home benefits from one of the finest beachfront locations of our Oahu vacation rentals. Steps from the white sand of Lanikai Beach—renowned for its pristine sand and waters— it’s hard to imagine a more picture-perfect setting.

From
US$2325 - 3875 /nt

View Villa Hale Hikina
Kailua, Oahu, Hawaii
6 br, 4.5 ba (2 Ensuite)

Please note that there is construction across from Mokulua Nui. Please enquire with one of our Villa Specialists for further details.

From
US$1670 - 3500 /nt

View Villa Mokulua Nui
Kailua, Oahu, Hawaii
5 br, 5.5 ba (5 Ensuite)

Place in Paradise is perfect for experiencing the laid-back vibe of Oahu’s Windward Coast. Up to 14 guests will sleep like Hawaiian Royalty in 5 bedrooms, making this spacious villa ideal for family gatherings, entertaining or retreats among friends.

From
US$1300 - 3500 /nt

View Villa Place in Paradise
Kailua, Oahu, Hawaii
5 br, 4 ba (3 Ensuite)

Experience the regal serenity of this tropical oasis, nestled between Oahu’s towering Koolau Mountain Range and turquoise Pacific waters. The main 4-bedroom villa draws inspiration from the colonial-style Queen Emma Summer Palace and a charming guest house sits at the far end of the pool.

From
US$1625 - 3125 /nt

View Villa Olu Olu Estate
Kailua, Oahu, Hawaii
4 br, 3 ba

Welcome to paradise. Over the years, Oahu’s Lanikai Beach has consistently been voted one of the world’s best, and you’ll find Honu Heaven just steps from its white sands.

From
US$1575 - 2750 /nt

View Villa Honu Heaven
Kailua, Oahu, Hawaii
4 br, 3 ba

Kailuana Beachfront Estate is located in the premier part of Kailua Bay where the sand is at its widest and the still turquoise waters most inviting. From your direct beach access, an expansive oceanfront lawn provides ample privacy and ambience for leaving the worries of the world behind.

From
US$1300 - 2500 /nt

View Villa Kailuana Beachfront Estate

Ko Olina

Ko Olina, Oahu, Hawaii
2 br, 2 ba (1 Ensuite)

Experience the best of both worlds at Hale Honu: the tranquil bliss of a private beachfront escape and the convenience of on-site amenities, upscale shops, fine dining and activities. This spectacular Hawaiian penthouse dream is located on the Ocean Tower’s 15th floor at the renowned Ko Olina Beach Villas.

From
US$625 - 1500 /nt

View Villa Hale Honu
Ko Olina, Oahu, Hawaii
2 br, 2 ba (2 Ensuite)

Hala Papakea is the perfect Oahu escape, whether you seek peace or play, romance or camaraderie. Located on the island’s beautiful west coast, this luxurious 2-bedroom villa enjoys a lagoon-side perch on the grounds of the famous Ko Olina Beach Villas Resort.

From
US$795 - 1500 /nt

View Villa Hale Papakea

North Shore

North Shore, Oahu, Hawaii
5 br, 7.5 ba (5 Ensuite)

A dazzling Hawaiian vacation estate totally unique in its unmatched grandeur, O Kekai is located on Hawaii’s remote northern shore with a vast and majestic oceanfront. This villa can host up to ten visitors, with five beautifully fashioned guest suites, seductive ocean views and an interior decor style that is so unbelievably opulent and eclectic, guests will remain wondering how this home was ever put together so artfully.

From
US$3500 - 10000 /nt

View Villa O Kekai
North Shore, Oahu, Hawaii
4 br, 4.5 ba (4 Ensuite), Pool

Hale Koa is located right on the beach on the windward side of the North Shore in Oahu. The North Shore is far from the glitz and glam of Waikiki – perfect for a relaxing or adventurous holiday with ample time spent in the fresh outdoor air.

From
US$1680 - 1800 /nt

View Villa Hale Koa

Waikiki

Waikiki, Oahu, Hawaii
3 br, 3 ba

Signature Ritz-Carlton luxury comes to the postcard-perfect sands of Hawaii’s most famous beaches at the Ritz-Carlton Residences Waikiki - 3 Bedroom Suite. Just minutes from the beach, world-class shopping and incredible golf, this gorgeous Oahu vacation rental puts you close to the best of the island.

From
US$2399 - 3299 /nt

View Villa Ritz-Carlton Residences Waikiki - 3 Bedroom Suite
Waikiki, Oahu, Hawaii
2 br, 2 ba

See Hawaii’s most iconic beach in a glamorous new light at a Ritz-Carlton Residences Waikiki - 2 Bedroom Suite. Part of a beautiful new development just minutes from Waikiki Beach and the world-class shopping and dining of Luxury Row, the suites offer guests the brand’s renowned service in the setting of a stylish private villa.

From
US$1399 - 2699 /nt

View Villa Ritz-Carlton Residences Waikiki - 2 Bedroom Suite
Waikiki, Oahu, Hawaii
1 br, 1 ba

At this coveted holiday destination in Oahu, the endless Pacific stretches out before you while legendary service awaits. Here, in vibrant Waikiki and just a five minute walk to the beach, the Ritz-Carlton Residences are perfectly positioned at the oceanfront gateway to this colorful and aromatic island paradise.

From
US$899 - 1599 /nt

View Villa Ritz-Carlton Residences Waikiki - 1 Bedroom Suite