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Top 10 Kahala Luxury Vacation Rentals

As the perfect luxury vacation rental property, Kahala, Hawaii combines island style and a Pacific Ocean-front atmosphere with first-rate amenities including private swimming pools, spas, and oceanfront views. With so many options to choose from, it’s important to consider all of the details when selecting your luxury Kahala vacation home or rental. To help make your selection process easier, we’ve compiled a list of some of our favorite Kahala luxury vacation homes and why they are so great.

Banyan Ohana Vacation Rental on Oahu
Average $10,893/night

Banyan Ohana

Kahala, Hawaii

Banyan Ohana is Oahu’s most luxurious vacation rental near the foot of Diamond Head. The exquisite home features seven bedrooms, eight full baths, and a half-bath, encompassing 14,000 square feet all within a private beachfront estate. This stylish and…

8 Beds

9 Baths

8 Bedrooms

Kahala Bridge Estate Vacation Rental on Oahu
Average $4,427/night

Kahala Bridge Estate

Kahala, Hawaii

This spacious beachfront estate is situated on lush tropical grounds, nestled in between palm trees. Enter the grounds thru the privacy gate to enjoy two swimming pools, Jacuzzi, waterfalls, and your private tennis court. Cottage Pool Heated…

8 Beds

7 Baths

7 Bedrooms

Moana kiʻi kiʻi Vacation Rental on Oahu
Average $4,000/night

Moana kiʻi kiʻi

Kahala, Hawaii

This oceanfront crown jewel – a modern diamond head home – offers a penthouse atmosphere for entertaining or quiet days watching ocean waves. This is a truly one-of-a-kind property with beach access. Located very near the Doris Duke “Shangri La,”…

5 Beds

5 Baths

4 Bedrooms

Kahala luxury property Secluded Kahala
Average $3,780/night

Secluded Kahala

Kahala, Hawaii

Ideal for multi-generational families and golf enthusiasts, this exquisite five-bedroom, four-bath home blends both island-style and Balinese touches to create the ultimate vacation home. Spread over 20,000 square feet, this property sleeps 14 guests…

11 Beds

4 Baths

5 Bedrooms

Seaside Villa Vacation Rental on Oahu
Average $3,034/night

Seaside Villa

Kahala, Hawaii

Your very own oceanfront oasis awaits you at Seaside Villa, a premier 4 bedroom and 4 bathroom estate residing on the cliffs of scenic Oahu. When you traverse through the doors of this Balinese-inspired vacation rental, you’ll step into a paradise that features…

4 Beds

4 Baths

4 Bedrooms

About Kahala, Oahu

Located near the Diamond Head State Monument, Kahala, which means Amberjack Fish, used to be known as Waialae. Come visit this flatland area, once a pig farming community, now an upscale neighborhood. From shopping and dining, to water sports, and swimming with the dolphins, Kahala has an amazing array of activities, luxury vacation homes, and sights for you. Come to relax or come for adventures.


For a great mall shopping experience, including a theater and Whole Foods shop, come to Kahala Mall. From boutiques and department stores to specialty eats and dine-in and carry-out meals, this mall has you covered. It also serves as a route stop on the bus line, if you are needing to get around. More shopping awaits you if you would prefer to travel up to Waikiki, about 12 minutes by car away. Waikiki is known for its upscale shopping experience. 

KCC Farmer’s Market

Grab some reusable shopping bags and get up early on a Saturday to visit the KCC Farmer’s Market. No need for coffee or breakfast first, come hungry and grab a coffee while you shop. Open to the public at 7:30 am, parking gets crowded after 9, so you will want to arrive early. Buy some fresh produce, and taste all the fresh baked goods and delicious treats the market has to offer. Take home some fresh honey with your produce and seafood. If you need, you can grab an Uber or Lyft from Waikiki or the Kahala Mall to the Farmer’s Market.

Mau’umae Trailhead

For the experienced hiker who is not afraid of a moderate to difficult trail, head on over to Mau’umae Trailhead. Explore the 10.6 kilometers out and back trail. This is a difficult but rewarding hike. At the top, you are rewarded with spectacular views below. The first peak is only about two and a half miles into the hike, and also will reward you with amazing views, if you are short on time or need something shorter.

Diamond Head Crater Hike

Once used as a military post for preventing attacks on Hawaii, you can now enjoy the same views at the top of this 1.6-mile round trip moderately rated hike. The summit affords you panoramic scenic views of the ocean, Waikiki, and the surrounding areas below. Standing on the edge of a 300,000-year-old crater will take your breath away. Absolutely stunning. It only takes about an hour to reach the top and be rewarded for your efforts. This is a must-do hike if you are able.


When you have had your fill of hiking and shopping, head to the beach to relax. There is no shortage of beaches in the area for you to enjoy, here are a few very close for you. Kahala Beach is the biggest and closest. Black Point Beach is just up the way and more secluded. Cromwell’s beach just a little bit further has more locals, fewer tourists, and is more secluded than Kahala.

Dolphin Quest

Situated very near Kahala, about six minutes away, you will find the extraordinary Dolphin Quest Experience. If you have ever dreamed of swimming with the dolphins, this is where you need to come! Book your experience before you go, so you are sure to have the time of your life. Or pick one of many Kahala luxury home rentals nearby and go daily.

Wai’alea Country Club

Golfers will take delight in this course so close to Kahala. This is a private course featuring three sets of tees. The fairways and greens are Bermuda Grass. Come enjoy this good walk spoiled. Plenty of close by Kahala luxury home rentals as well.


Since you are only a few miles from Waikiki, making the approximately twelve-minute trip up there for a day should be on your agenda. Feel the legendary white Waikiki sands on your feet, and enjoy upscale boutique shopping, and dining experiences. While you are in Waikiki, visit the Aquarium! Not far away is the Honolulu Zoo, should you want to explore it while you are in Waikiki.