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Luxury rentals in O‘ahu

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Top-rated luxury holiday rentals in O‘ahu

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LUXE
Villa in Honolulu
Kahala Oceanside
This spectacular oceanfront villa on Oahu is situated within walking distance of Kahala Beach, about a mile from Diamond Head Lookout, with expansive views of the Pacific Ocean. The gated property offers exquisite privacy and high-end amenities for relaxation and entertainment, including a lagoon-style swimming pool and hot tub, outdoor entertainment area, and gourmet kitchen. The villa comprises a main house with two master suites, along with four deluxe private cottages arranged around a lush garden sanctuary—accommodating up to fourteen guests. A wide array of deluxe services and activities are available. The home is nestled amid lush tropical trees yielding to expansive ocean vistas, evoking an ambiance of seaside oasis. Generous outdoor living areas on both levels invite you to long days and evenings in the open air. Soak your body in the stone-framed hot tub and plunge into the refreshing pool. Sunbathe on elegant lounge chairs on the upper balcony, or relax in the cool shade of the lower veranda. Kindle the barbecue in the afternoon and relish alfresco meals in the dreamy breeze. The main house opens directly to the veranda as well as the interior gardens, creating a lovely crosscurrent of ocean air. The cavernous living room features double-height ceilings and comfortable sofas, with a wide threshold leading into the beautiful dining room. Pocket doors fuse the indoor and outdoor dining areas, forming an ample venue for dinner parties. Multiple dens offer quiet retreats for afternoon downtime or late-night fun. The main house includes two ocean-view master suites, each with a king bed, walk-in closet, sound system, and ensuite bathroom (one of which includes a lovely tub). The Kahala Master opens directly to a private furnished balcony, while the Waikiki Master has its own interior living room. Each of the four garden cottages is essentially a master suite, with king bed, walk-in closet, and ensuite bathroom. The Maui Cottage includes a kitchenette, while the Hawaii Cottage has its own fully equipped kitchen and a queen-size sofa bed. The villa is just steps from Kahala Beach and about a mile from Wai’alae Beach. Kahala Mall is less than two miles away, and you're within easy reach of Waikiki, Honolulu Zoo, Ala Wai Golf Course, and much more. Copyright © Luxury Retreats. All rights reserved.  HAWAII TAX ID #:053-250-7136-01 BEDROOM & BATHROOM • Bedroom 1 - Kahala Primary: King size bed, Ensuite bathroom with stand-alone rain shower and bathtub, Bidet, Dual vanity, Sound system, Walk-in closet, Television, Ceiling fan, Air conditioning, Direct access to private balcony with outdoor furniture, Ocean view • Bedroom 2 - Waikiki Master: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Bidet, Sound system, Living room, Walk-in closet, Television, Sound system, Ceiling fan, Air conditioning, Ocean views Hawaii Cottage  • Bedroom 3: King size bed, Queen size sofa bed, Ensuite bathroom with shower/bathtub combo, Bidet, Living room, Television, Sound system, Ceiling fan, Fully equipped kitchen, Air conditioning Maui Cottage  • Bedroom 4: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet, Living room, Television, Sound system, Ceiling fan, Kitchenette, Air conditioning, Garden views Kauai Cottage  • Bedroom 5: King size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Walk-in closet, Television, Sound system, Ceiling fan, Air conditioning, Garden views Oahu Cottage  • Bedroom 6: King size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Sound system, Walk-in closet, Television, Ceiling fan, Air conditioning, Garden views FEATURES & AMENITIES • Wine fridge • Alarm system • Baby equipment available upon request OUTDOOR FEATURES • Security Cameras • More under “What this place offers” below STAFF & SERVICES Extra Cost (advance notice may be required): • Mandatory mid-stay cleaning for stays longer than 14 days  • Hula lessons • Dolphin experience • Canoe surfing • Photoshoot • More under “Add-on services” below LOCATION Points of Interest:  • 3 minute drive to Diamond Head State Monument • 6 minute drive to Kapiolani Park • 9 minute drive to Royal Hawaiian Center • 4.8 miles to Ala Moana Beach Park • 5.1 miles to Ala Moana Shopping Center • 7.0 miles to Iolani Palace • 7.2 miles to Downtown Honolulu • 7.9 miles to Chinatown • 8.4 miles to Bishop Museum • 14 miles to Pearl Harbor/USS Arizona Beach Access: • 8 minute drive to Waikiki Beach • 19 miles to Lanikai Beach Airport: • 12 miles to Daniel K. Inouye International Airport (HNL)
Professional Host
LUXE
Villa in Kahuku
Moani Kaiolohia
Swim in the Pacific surf and play games on your private sport court at this villa on Oahu’s north coast. Perfectly designed for breezy relaxation, the home features superbly equipped interiors opening to shaded outdoor living areas with alfresco dining and a hot tub. Lush gardens and trees yield to pristine sands and panoramic ocean views. Take a short drive to Turtle Bay Resort or Mālaekahana State Recreation Area. The 3-story house features multiple living and dining areas both indoors and out, along with a fully equipped kitchen and additional kitchenette. All 3 levels open to spacious decks with lovely views through the swaying trees at the shimmering water. Enjoy basketball, badminton, or paddle tennis on the court, before cooling off with a dip in the sea. Gather for outdoor meals from the barbecue and crawl into the spa for a nighttime soak. Far from Oahu’s more tourist-heavy south shore, the north coast offers pristine natural beauty, an array of world-class beaches (including Sunset, Waimea Bay, and Ehukai), and exceptional golf courses. Drive about 15 minutes to the Polynesian Cultural Center, or park the car at Mālaekahana State Recreation Area for a walk to Goat Island. Turtle Bay Resort features 2 championship courses, a spa, and much more. Surfing pilgrims will want to visit the famous Banzai Break on the northwest coast. The villa is about 5 minutes from the nearest supermarket. Copyright © Luxury Retreats. All rights reserved. License TA-056-157-7984-01 TVU - NUC1915 BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower, Safe, Ceiling fan, Direct access to balcony, Ocean view • Bedroom 2: Queen size bed, Shared access to hallway bathroom with Bedroom 3, Shower/bathtub combo, Safe, Ceiling fan, Direct access to terrace • Bedroom 3: Queen size bed, Shared access to hallway bathroom with Bedroom 2, Shower/bathtub combo, Safe, Ceiling fan • Bedroom 4: 2 Twin size beds, Shared access to hallway bathroom with Kitchen, Shower/bathtub combo, Ceiling fan • Bedroom 5: Queen size bed, Shared access to hallway bathroom with Bedroom 6, Stand-alone shower, Safe, Ceiling fan, Direct access to balcony • Bedroom 6: 2 Twin size beds, Shared access to hallway bathroom with Bedroom 5, Stand-alone shower, Safe, Ceiling fan OUTDOOR FEATURES • Outdoor living space • Boogie boards • Terrace STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below
Professional Host
LUXE
Villa in Honolulu
Gail Street Villa
Gail Street Villa - 5Br - Sleeps 10
Professional Host

Other great luxury holiday rentals in O‘ahu

LUXE
Villa in Haleiwa
The Sullivan Estate & JK7 SPA Retreat
LUXE
Villa in Kailua
Kehaulani
Professional Host
LUXE
Villa in Kahuku
O Kekai
Professional Host
LUXE
Villa in Honolulu
Kalakaua Villa
Professional Host
LUXE
Villa in Honolulu
Niuiki Oceanfront
Individual Host
LUXE
Villa in Honolulu
Espacio Waikiki Penthouse

All about O‘ahu

Planning an Oahu vacation? We’re here to help!

Hike Diamond Head

Offering up spectacular panoramic views of Honolulu and Waikiki beach, a hike to the top of Diamond Head is a great way to get outdoors, get some exercise, and enjoy the natural beauty of Oahu. Although it looks like a long way up, if you choose the right trail you can reach the peak in a little under an hour.

To reach the easiest trail, use the eastern entrance to the park, head for the crater and look for signs directing you to the Diamond Head trailhead. Though the trail is paved most of the way (it was originally built by the US Army), it’s still a good idea to wear sturdy sneakers or walking shoes, and remember to bring water, snacks, and sunscreen. Lastly, don’t rush; take the time to stop at the lookouts along the way for gorgeous views of the ocean and the city spread out below you.

Surf the North Shore

Perhaps the most famous surfing destination in the world, Hawaii’s North Shore is the home of big wave surfing. In the winter months, waves can reach up to 30ft, and the beaches draw surfers from all over, who come to test their skill at competition time. The major draw is the Vans Triple Crown of Surfing, which is held in November and December and has been running since 1983. It’s a great event to watch from the shore, whether you know the intricacies of the sport or not—watching someone take on the iconic Pipeline wave is an experience you’ll remember forever.

If you want to try your hand at surfing more manageable swells, the best waves for beginners and novices are Puaena Point at Haleiwa Beach Park and Kawela Bay. Surfing has its own internal rules—so always let experienced riders go ahead of you and try not crash someone else’s wave.

Shop ‘til you drop

No matter what fashionable souvenir you’re looking for, you’ll find a shop with your name on it in Oahu. From luxury boutiques to wallet-friendly outlet stores and all the big name chains, there’s everything you could think of and more.

Serious shoppers can get their fix at Ala Moana Center in Honolulu. It’s the largest outdoor shopping center in the world, which means you can still catch some rays and top up your tan in between browsing. You’ll find all the major department stores here—including Macy’s, Nordstrom, Neiman Marcus, and Bloomingdales, but for something a little different, make sure you check out Japanese department store Shirokiya, which also has delicious lunch options.

If you more in the market for high-end labels, make a beeline for Luxury Row, located on Kalakaua Ave in the center of Waikiki. You can shop for something sparkly at Tiffany & Co, treat yourself to some Chanel ballet pumps and pick up some shades from Gucci to look good while you do it. There’s also a Sephora for all your beauty buys.

If you love a good deal, the outlet stores at Waikele, 30 mins outside of Waikiki, are sure to please. There are over 50 shops here, including Kate Spade, Barney’s, Coach, and Saks Off Fifth.

Hit the greens

The Fazio course is generally considered to be an easier play, and has equally beautiful scenery, running along a coastline lined with palm trees. You’re guaranteed lovely ocean views at every turn. If you prefer to walk while you golf instead of hopping in a cart, the manageable size of the Fazio course makes it an ideal choice.

Experience the luxury of our Oahu vacation rentals

Where to stay: Waikiki

Close to the airport, Waikiki beach and all the shopping and dining options you could wish for, our villas in Waikiki are great for families who like to switch up their activities from one day to the next.

Where to stay: Kailua

If you’re thinking about spacious accommodation right on the beach, then take a look at a Kailua vacation rental . Sleeping up to 18 people, with shaded lanais, swimming pools, and indoor/outdoor style living, if you’re planning a big group getaway there are some great options here.

Where to stay: The North Shore

Does getting up early to hit the waves sound like your kind of getaway? If so, one of our vacation rentals on the north shore of Oahu will be a dream come true. You’ll be able to monitor the weather from the comfort of your lanai, then grab your board and head out in no time at all. Most of our properties in the area sleep up to 10 people, so your buddies can come too, and with gas grills and outdoor dining areas, there’s plenty of space to cook up a feast and relive the day’s adventures over a cold beer.

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