Oahu Vacation Rentals
115 matching rentals.Most Popular
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Kailua
8 Bedrooms, 10 Baths, Sleeps 16. Highest Level of Luxury, Lagoon Pool, Recreation Cabana, Movie Theater, Concierge, Separate Guest House, Luxurious, Exquisite Interiors, Spacious Yard, Beachfront Estate.
Rarely do oppo...
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per night
8 beds
10 baths
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Waimanalo Beach
Embrace this 5 Bedroom, 4 full bathroom, 2 half bathroom, two story Hawaiian residence and let yourself experience serene and peaceful waters while enjoying your refreshing private pool. Beautiful Villa at the end of Wa...
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per night
5 beds
3.5 baths
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Aina Haina
Hawaiian jewel “Beachfront Oasis” the former home of John Travolta and Kelly Preston, until it was purchased and renovated by kathy ireland Worldwide, is a striking, mid century, 3 bedroom, three baths walled and gated ...
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per night
3 beds
3 baths
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Listings
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Kahala
If paradise had a home it would be here, in the sun, on the beach, nestled in a cove at the foot of Diamond Head. If luxury had a face it would be this stunning 7 bedroom, 13,000 sq ft, gated, oceanfront Royal Circle es...
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per night
7 beds
7.5 baths
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Kailua
8 Bedrooms, 10 Baths, Sleeps 16. Highest Level of Luxury, Lagoon Pool, Recreation Cabana, Movie Theater, Concierge, Separate Guest House, Luxurious, Exquisite Interiors, Spacious Yard, Beachfront Estate.
Rarely do oppo...
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per night
8 beds
10 baths
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Lanikai
Only 30 minutes from downtown Honolulu, a serene and enchanting hideaway exists beside the sea in Lanikai. Situated opposite the Mokulua Islands in Lanikai Bay with 230 ft. of white sand beach, this 1.3 acre Polynesian ...
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per night
7 beds
9.5 baths
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Kailua
O'ahu Lani is children-friendly and family oriented and the only villa on the island that includes fully customized service and gourmet meals. The villa occupies a superb location on Kailua beach-rated one of the ten fi...
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per night
10 beds
10 baths
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Kailua
Alii O Kailua is one of the newest, most striking and contemporary executive beachfront estates on world renowned Kailua beach. Constructed in 2008, the estate features two homes (main house and guest house) separated b...
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per night
7 beds
7.5 baths
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Kailua
A Grand Beachside Estate on beautiful Kailua Beach. This premier luxury rental is set on 1.5 acres of world-famous Kailua beachfront property and boasts nearly 11,000 square-feet of grand construction and spectacular de...
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per night
8 beds
8 baths
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Waikiki Banyan
This stunning executive estate at the base of Diamond Head offers complete privacy and a luxurious, romantic experience for even the most discriminating guests. Beautiful manicured tropical gardens greet you at the entr...
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per night
7 beds
8.5 baths
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Diamond Head
Stunning beachfront home in Diamond Head. The Luxury at Diamond Head, located at the slopes of Diamond Head-Honolulu's most prestigious neighborhood. This gorgeous beachfront property is truly suited for celebrities. Th...
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per night
5 beds
4.5 baths
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Lanikai
Flush with success in New York in the 1970s, hairdresser Paul Mitchell came to Hawai'i in search of peace and renewal. When he first laid eyes on Lanikai on the windward coast of O'ahu, he knew he had arrived in paradis...
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per night
7 beds
6 baths
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Lanikai
Pristine Lanikai Beach, rated among the worlds top beaches for both beauty and clean water; where vacationers flock to enjoy Hawaiian island living in the few and rarely available vacation rentals located on this beach-...
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per night
5 beds
4 baths
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Kailua
Beginning in April 2011, Kailua's newest beachfront home will be available for lease. Located on the most pristine beach in all of Oahu and just 20 minutes from the airport/Waikiki, this spectacular custom estate is a s...
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per night
5 beds
5 baths
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Kailua
For those seeking respite, the Paradise Plantation is a Presidential oasis and the anecdote to the stresses of everyday life.
Paradise Plantation is a rare jewel that comes fully appointed with Plantation style finishe...
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per night
5 beds
5.5 baths
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Kailua
This gorgeous oceanfront property has 13,000 sq ft, double gate with semi-circular driveway, a beautiful re-landscaped garden with a new extensive, travertine tiled, lanai. The house has 4 bedrooms, a massage room (whic...
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per night
4 beds
4 baths
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Diamond Head
Stunning beachfront home in Diamond Head. The Empress at Diamond Head, located at the slopes of Diamond Head—Honolulu’s most prestigious neighborhood. This gorgeous beachfront property is truly suited for celebrities. T...
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per night
5 beds
4.5 baths
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Lanikai
One of our favorite homes, Villa Lanikai Ali'i is a 5 bedroom, 4.5 bathroom, true state-of-the-art masterpiece. Set on half an acre of tropically landscaped grounds, and located on the widest part of Lanikai beach, this...
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per night
5 beds
4.5 baths
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Kahala
Thought you could never afford to take your entire family on a Hawaiian Vacation?... Think Again! This Resort-like Private Kahala Beach estate is perfect for large groups or family vacations. The Kahala Mini Resort is o...
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per night
7 beds
6.5 baths
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Kailua
Kailua Beach! Beachfront elegance at its finest has been captured under the roof of this Plantation Estate at Paradise Point, tucked privately at the edge of the World's #1 Beach. Paradise Point the Birthplace of Hawaii...
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per night
5 beds
5.5 baths
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Kailua
The exclusive 5 Star Plantation Estate at Paradise Point at Kailua Bay on the Hawaiian Island of Oahu, offers classic beachfront elegance at its finest. In December 2008 and 2009, President Barack Obama and his family p...
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per night
5 beds
5.5 baths
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Kahala
This spacious complex, situated on manicured beachfront grounds, features two swimming pools, tennis court, two waterfalls and an abundance of tropical foliage. Located just a short walk down the beach from the Kahala H...
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per night
7 beds
6 baths
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Kahala
Bedrooms: 7. Bathrooms: 6
Ener the lush tropical grunds thru the privacy gate and enjoy a swim in one of your sparkling pools or a game of tennis. Inside this beautiful mansion are gourgeous slate and wooden flooring, ...
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per night
7 beds
6 baths
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Reviews
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love it
by
Colleen D.
on 05/10/13
We had 25 family members of all ages. The view was wonderful, the place was great... I cant wait to go back, If I could move in tomorrow forever it would not be soon enough.
Read more
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Blog Posts
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April 16, 2013
Driving up Kamehameha Highway, you’ll smell the distinctively sweet, tangy scent of pineapples before you see them. Most people come to the Dole Plantation to tour the beautifully landscaped gardens o...
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March 27, 2013
This is another lunch I had at Kahala Mall with my friend Aaron, at Ba-Le. It looks like the chicken egg roll dipping-sauce has a straw in it but that’s just a parsley stem from the teriyaki chicken s...
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January 16, 2013
The volcanic Hawaiian islands offer tourists beaches of golden and white sands, blue Pacific Ocean waters and some tremendous surfing. Some get very busy, especially at weekends when locals pack a pic...
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December 31, 2012
We were headed specifically for Sunset Beach, which is famous, because we saw it on t-shirts at Walmart... there's also a fantastic amount of surfing that happens in the winter months of Hawaii. We di...
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December 20, 2012
Last Monday, Papa Tony, Owen, and I visited Mokoli'i, also known as Chinamen's Hat. Mokoli'i is a very small island off of the eastern shore of Oahu. It is famous for being the backdrop to movies and ...
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November 29, 2012
About three-quarters of the way to the falls, we passed a magnificent view of Kailua. Just behind the mountains is the ocean. Below the mountains are a giant canopy of trees. Whether it is hiding anim...
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November 29, 2012
Remember back in 2008 when Barack Obama vacationed in Hawaii? Over the Thanksgiving weekend, I had a “Be Like Barack Vacation” on a very miniscule scale. The day started early, picking up passengers, ...
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November 27, 2012
It was the morning after Halloween and I was returning from my early morning swim to my new digs, # 639, which had a marina and city view. The elevator fills up quickly, mainly with seniors at this ea...
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November 25, 2012
TJ and I spent Thanksgiving in Oahu this year. We stayed in a condo on the North Shore in a town called Punalu'u. Sunrise from our lanai....
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November 21, 2012
A few weekends ago, the Joneses visited the Dole Plantation with the goal of attempting to successfully navigate the Pineapple Garden Maze, the world's largest permanent outdoor maze. Mission Accompli...
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