Destination Photo

Kailua Vacation Rentals

Our Favorite Vacation Rentals in Kailua (Oahu)

Kailua (Oahu) Vacation Rentals with a Pool

Kailua (Oahu) Vacation Rentals with Wi-Fi

Kailua (Oahu) Pet-Friendly Vacation Rentals

Kailua Oahu Travel Guide

This Hawaiian paradise town is perfect for any beach lover’s vacation. The town is known as a resort town on the island of Oahu along the shore. Hawaii’s picturesque beaches have clear turquoise waters and soft white sand, as well as excellent surf or swim spots up and down the coast. Top beaches in Kailua include Lanikai Beach, ranked as one of the best beaches in the world, and Kailua Beach, once ranked as the number one beach in the United States.

Things to Do in Kailua Oahu

Hike the Lanikai Pillbox Trail or the Kaiwa Ridge Trail to get the best views of the ocean all around. The Maunawili Falls Trail is another popular hiking spot in town. The 2.5-mile trail leads you to the stunning swimming hole and scenery at Maunawili Falls. The Kailua Farmer’s Market is something you truly can’t miss for all the locally grown fruits and veggies, as well as the handmade souvenir crafts.

Best Time to Visit Kailua Oahu

Hawaii is beautiful and warm all year round, but the best time to visit Kailua is from January through May. Kailua is full of sleepy, relaxed beach town vibes all around. Locals in town are relaxed and open-minded, and most residents work hard to preserve the environment and local culture.

Price and Availability in Kailua (Oahu)

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
The most expensive month to stay in a vacation rental in Kailua (Oahu) is in July, while the cheapest month is in September. The most popular time to book a vacation rental in Kailua (Oahu) is in the high season in July. Kailua (Oahu) has its low season in September, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Kailua (Oahu) tends to be Sunday, while the most expensive day tends to be Tuesday. Vacation homes in Kailua (Oahu) tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Kailua (Oahu)

86º 73º
0.74
87º 71º
1.46
90º 70º
5.55
87º 71º
6.53
85º 67º
5.85
82º 65º
1.78
85º 66º
1.37
84º 62º
6.2
84º 64º
2.46
87º 63º
4.14
83º 65º
2.81
86º 73º
0.66
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Rainy days
This climate histogram shows you the weather patterns in Kailua (Oahu). The warmest months in Kailua (Oahu) are April and September, when temperatures reach 90 ˚F. The coolest month is February, when temperatures drop to 62 ˚F. The wettest month in Kailua (Oahu) is October with 6.53 inches of rain, while the driest month is June with 0.66 inches of rain.

What Expert Travelers Think