Kailua means “two seas,” a fitting name that references the two lagoons that frame the Island of Oahu and the currents that flow through them, driven by steady trade winds. These trade winds contribute to surf that is world-renowned, encouraging watersport enthusiasts, surfers, wind boarders, and kite-flyers to visit the beaches of Kailua.
Located on the eastern side of the island of Oahu, Kailua's beaches and coves are so enchanting that if you never venture beyond the sand and waves during your stay, you'll be perfectly happy with your trip to Hawaii.
When is the best time of year to visit Kailua, Hawaii?
Kailua boasts a warm, tropical climate year-round. There's literally no wrong time to visit this island paradise. Peak season in Kailua comes twice a year, the first during the winter months of December through March. Crowds peak again in the summer months of June through August. Travel here in the off-season months if you'd like to find lower rates and more hotel options.
Weather patterns in Kailua remain steady, though the tropical climate means there's always a chance of rain. In the winter months, temperatures average in the mid-70s. Temperatures peak in the mid-80s during the summer. There are plenty of things to do year-round. Even the Kailua Farmers Market runs throughout the year, so you can pick up a local coconut or pineapple on your way back to the hotel.
You can hit the surf at any time, but you may wish to pack a wetsuit if you'll be in the water during the winter months for an extended period. The cooler months are perfect for exploring the landscape, such as taking a strenuous hike to the peaks of Olomana. At the summit, you'll be treated to invigorating trade winds and incredible views. Come spring and summer, head over to Kāneʻohe Bay, the largest bay in the Hawaiian Islands, for a snorkel tour or dive in the area's coral reefs.
It's always fun to visit Kailua, but if you plan your trip around the area's activities and festivals, you'll be in for an even greater treat. In April, the "I Love Kailua Town Party" brings family fun to the streets with food vendors, crafts, kids' rides, and live music. Enjoy live outdoor performances by the Hawaii Symphony Orchestra in May and June, and on Independence Day, Kailua celebrates with a parade, honoring veterans with marching band performances and more.
Below is a chart of the current pricing seasonality of hotels and motels in Kailua, HI:
Kailua by Star Rating
Below are 3 charts demonstrating mean rate trends by star rating class in Kailua, HI. You can use these line graphs to evaluate the least expensive time to book a room in Kailua for upcoming travels.
What are the luxury hotels around Kailua, HI?
4 Star Average Prices: $192.60
The Kahala Hotel & Resort in Eastern Honolulu is an Oahu oasis, away from the hustle and bustle of Honolulu, and about a 40-minute drive from Kailua. This luxurious property offers impressive amenities you won't find anywhere else, like a dolphin pool on-site. Book a room close by, and you and your kids will be endlessly entertained watching these friendly creatures. Children will also love the dedicated children's pool, where they can splash to their hearts' content. The Kahala Hotel's babysitting service is available for a modest surcharge if you'd like some time to yourself for a while.
Adults can enjoy another pool on the property where they can enjoy a beverage from the poolside bar. Of course, there's beach access right behind the hotel where guests love to play sports and sun on the sand. A visit to the spa will relax every muscle after a day's exertions, and you can also indulge in 24-hour room service. The Kahala offers every convenience, even down to a shuttle bus to take you into town to shop and explore.
If you prefer to stay in Honolulu but plan to drive out to spend time in Kailua, you'll be extremely comfortable at The Ritz-Carlton Residences, Waikiki Beach in Honolulu. Guestrooms offer pristine views from private balconies, and you can even cook in your own kitchen, which is equipped with a stove top and all the essentials. Beach access and upscale furnishings make this a stylish hotel destination near Kailua.
Where are the most affordable hotels near Kailua, HI?
3 Star Average Prices: $167.34
For a quiet residential option, head to Aqua Skyline at Island Colony in Honolulu. This apartment-style hotel lies just 10 miles from Kailua. Guestrooms are stylishly outfitted with modern furnishings and private balconies. You'll find convenience here, too, with a kitchenette and air conditioning, plus a coffee shop downstairs for a quick breakfast before heading out to shop and explore. Spend the late afternoon sunning at the outdoor pool in a lounge chair under the shady arbors.
You can opt for a classic Hawaiian resort when you stay at the Pagoda Hotel. Though this hotel has been a mainstay of Honolulu for many years, its charm has only grown over the years. This value property, just over half an hour from Kailua, is convenient to spectacular hiking trails, the University of Hawaii at Manoa, and shopping options including the Ala Moana Center, the largest shopping mall in Hawaii.
The namesake Pagoda inspires whimsical Asian influences in the hotel's decor, from the outdoor pool area to bamboo motifs and furniture inside. A soaring open dining area, full of striped awnings and ceiling fans, makes for a fun dining experience. In the guestrooms, jaunty jade-green tones continue the Eastern-inspired theme. You'll enjoy convenient amenities like free Wi-Fi, flat-screen televisions, and a kitchenette. Daily housekeeping helps you stay tidy and relaxed throughout your stay.