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Kailua’s Most Luxurious Vacation Rentals

Sorted by most expensive per night.

Average $11,000/night

Kailua Cabana

Kailua, Hawaii

Relax and unwind at this stunning estate with direct access to the beautiful sandy beaches of Kailua. This exquisite 5 bedroom main residence offers 11,000+ sq ft of lavish living plus a gorgeous separate 3 bedroom guest house. Incredible details, expert craftsmanship…

8 Beds

8 Baths

8 Bedrooms

Average $10,000/night

Kailua Kahakai

Kailua, Hawaii

These two magnificent homes both sleep 12 people (24 total) is nestled on two acres of land, that has its own shared swimming pool and hot tub, and the most beautiful sandy beach imaginable at your doorstep. It is completely furnished and beautifully maintained…

12 Beds

12 Baths

12 Bedrooms

Kai Moena Vacation Rental on Oahu
Average $8,282/night

Kai Moena

Kailua, Hawaii

This luxury vacation rental sits on nearly 60,000 sq. ft. of prime Kailua Beach property with 225+ sq. ft. of linear beach frontage featuring soft sand, blue water, and spectacular views of Kailua Bay. Two separate rental houses by award-winning architect James McPeak…

10 Beds

8 Baths

9 Bedrooms

Obama Vacation House in Kailua Hawaii
Average $4,737/night

Obama Vacation House

Kailua, Hawaii

This Presidential vacation home is fit for a king. Immediately you are surrounded by luxury. Smooth granite countertops, tiled accent walls, hardwood floors, and warm wood shiplap ceilings are just some of the exquisite details you experience here…

7 Beds

6 Baths

5 Bedrooms

About Kailua, Oahu

Located on the windward side of Oahu, Kailua means “two currents” or “two seas”. Possibly named for the two lagoons on the Island of Oahu, or the two currents running through Kailua Bay. Kailua has a rich human history, and the Kailua region was a gift from the rising Hawaiian Warrior, Kamehameha, when he conquered Oahu, to his Chiefs and warriors who aided his conquest.

Beaches in the area

Kailua Beach Park is two and a half miles of silky white sand blending with the mesmerizing teal waters. Steady trade winds, waters averaging seventy-five degrees year-round, and the protective reef provide perfect conditions for windsurfing and kitesurfing. If you have ever wanted to try stand up paddle boarding or kayaking, this beach is perfect for your first experience.

Lanikai Beach, sister to Kailua Beach, is one mile of the same white, silky sand and stunning turquoise waters. Lanikai lives up to its translation, “Heavenly Ocean”. Since there are no posted signs, finding Lanikai Beach can be a bit tricky. Look for the word “Lanikai” on a huge pillar in the area. The pedestrian entrance is located between residential homes on beach alleys. Lanikai Beach does not have any restrooms, showers, lifeguards, or picnic tables. Make sure to bring a cooler packed for the day, and make a stop at Kailua Beach Park nearby for the facilities. It is best to come to Lanikai Beach in the early part of the day, as the sun dips below the Koolau Mountains in the afternoon.

Hiking in the Area

You will want to make the short trek up to the Lanikai Pillboxes. This is a short, one-mile hike. Though the first part is quite steep, so this can be challenging for some in the beginning. The pillboxes themselves were shelter bunkers for soldiers during World War II. Also known as the Ka’iwa Ridge Trail, the Lanikai Pillboxes hike is considered one of the most scenic hikes. Providing the hikers with panoramic views of the coastlines, Koolau Mountains, and the Mokolua Islands in the distance. The entire hike round trip should take you from sixty to ninety minutes. Come before sunrise for some especially breathtaking scenes.

Maunawili Falls Trail is a moderate 3.9 kilometer (about 2.5 miles) hike to a spectacular waterfall in the Waimanalo Rainforest Reserve. Accessible year-round, the trail can be muddy in the rainy seasons. This hike makes a wonderful day trip, bring a picnic lunch, even bathe in the pool at the base of the falls, weather permitting.

If you are looking for a challenge, head up to Olomana Trail. This is a more strenuous 7.1 kilometer (approximately 4.5 miles) hike, rated as difficult, this hike is very rewarding to those who do it. 

Kaiwainui Marsh Trail is an easy trail, more of a relaxing nature walk. Enjoy this easy 4.7 kilometer (just under 3 miles) walk through the wetlands, observing the native Hawaiian birds in their natural habitats. This walk is family-friendly.

Golf Courses in the Area

Ko’olau Golf Club is breathtaking and scenic, and one of the toughest courses in Hawaii. Challenge yourself on this beautiful course. Or just enjoy the good walk spoiled.

Olomana Golf Links is considered President Obama’s favorite course. Located in Waimanalo, these eighteen holes are split into two distinctly different sets of nine. 

Pali Golf Course is a public course with breathtaking views of the Koolau mountain range as well as bay views of Kaneohe Bay. 

Restaurants and Eateries 

After so much exploring and so many adventures, your appetite will be ready for all the wonderful food Kailua offers you. Asian Fusion, Hawaiian, or American? Sandwiches and Burgers, Seafood, or Pan Asian? Barbeque, Mexican, Moroccan, or whatever strikes your fancy, you are sure to find it here. 


The average temperatures in Kailua range from 69* to 84* and rarely go below 65* or above 86*. The best time to visit for hot-weather activities is from May to October. With an average of about seven days per month of rain, and perfect temperatures year-round, Kailua is perfect at any time of the year to visit. 

Travel on the Island

For the most freedom of movement about the island, we would recommend renting a vehicle. You can take Uber or taxis around town. Also, there is public transportation via TheBus and TheHandi-Van.