Pool with waterfall with dining area and islands in background at Obama Vacation House luxury vacation rental, Kailua, Oahu, Hawaii
from $ 3,500 per night
Rent

Obama Vacation House Kailua, Hawaii

This Presidential vacation home is fit for a king. Immediately you are...

5

Bedrooms

7

Beds

6

Bath

5

Parking

Details »

Pool side with umbrella and beach chairs at Manu Iwa luxury vacation rental, Kailua, Oahu, Hawaii
from $ 700 per night
Rent

Manu Iwa Kailua, Oahu

This property is a legally established dwelling that is rented for 30...

3

Bedrooms

3

Beds

2.5

Bath

2

Parking

Details »

Poolside view of the back yard with trees and green grass at lihikai hale luxury vacation rental in Hawaii
from $ 700 per night
Rent

Lihikai Hale Kailua, Oahu

If you are coming to Kailua, you will want to secure this...

4

Bedrooms

4

Beds

3

Bath

2

Parking

Details »

Beautifully landscaped yard with bright blue pool and lawn chairs at Hale Malama luxury vacation rental, Kailua, Oahu, Hawaii
from $ 400 per night
Rent

Hale Malama Kailua, Oahu

This beautiful house and cottage can sleep ten and makes the perfect...

5

Bedrooms

7

Beds

4

Bath

3

Parking

Details »

Facing the beach and ocean with two lawn chairs at Kalama Hale luxury vacation rental, Kailua, Oahu, Hawaii
from $ 1,000 per night
Rent

Kalama Hale Kailua, Oahu

If you have ever wanted the ocean as your backyard, this vacation...

4

Bedrooms

6

Beds

3

Bath

2

Parking

Details »

Backyard facing back deck with pool and outdoor dining area at Kalaheo Hale luxury vacation rental, Kailua, Oahu, Hawaii
from $ 995 per night
Rent

Kalaheo Hale Kailua, Oahu

Featuring a private pool in an enclosed and private yard, you can...

5

Bedrooms

6

Beds

3.5

Bath

3

Parking

Details »

Beautiful pool, hot tub and water fall at Ocean Hale luxury vacation rental, Kailua, Oahu, Hawaii
from $ 2,500 per night
Rent

Ocean Hale Kailua, Hawaii

Putting you on a premier spot on the silky white sands of...

5

Bedrooms

5

Beds

5

Bath

2

Parking

Details »

Sweeping back deck facing the beautiful ocean at Royal Palm Hale luxury vacation rental, Kailua, Oahu, Hawaii
from $ 500 per night
Rent

Royal Palm Hale Kailua, Oahu

This gorgeous beach house has everything you want in a Hawaiian Vacation...

4

Bedrooms

5

Beds

3

Bath

2

Parking

Details »

Aerial view of pool, beach and ocean with clouds at Royal Palm Estate luxury vacation rental, Kailua, Oahu, Hawaii
from $ 6,500 per night
Rent

Royal Palm Estate Kailua, Oahu

Fit for royalty, Royal Palm Estate is exquisite in every way. Elegant...

7

Bedrooms

9

Beds

8.5

Bath

5

Parking

Details »

Pool side with palm trees and beach chair at Nanea luxury vacation rental, Kailua, Oahu, Hawaii
from $ 733 per night
Rent

Nanea Kailua, Oahu

This property is a legally established dwelling that is rented for 30...

4

Bedrooms

6

Beds

4

Bath

2

Parking

Details »

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. 

Weather

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.