Honest Pros and Cons of Living in Kailua

Honest Pros and Cons of Living in Kailua

Located on the windward side of Oahu, the idyllic town of Kailua offers a laidback small-town beach vibe with plenty of upscale urban amenities. From gorgeous beaches to vibrant cultural life and a tight-knit community, this suburb of Honolulu has it all.

Living in Kailua is unlike anywhere else in the country, with unparalleled natural beauty and a tropical climate that lends itself to unlimited sun, sand, and surf all year round. Those fortunate enough to call Kailua home benefit from residing in one of the most luxurious locations on the island.

While the advantages of living in Kailua are endless, there are also a few downsides to consider before moving to Hawaii.

Pros of living in Kailua

There is so much to enjoy when living in Kailua. A few of our favorite things about this fabulous Hawaiian town are listed below.

1. Laidback lifestyle

Everywhere you go on the island exudes the spirit of aloha, and Kailua is no exception. The locals believe in living a simple life surrounded by good friends and great food amidst the salty sea air. Residents spend most of their day in bathing suits and flip-flops as they relish the limitless opportunities for water sports, such as world-class surfing, snorkeling, kayaking, swimming, scuba diving, and more. The Tradewinds provides an unsurpassed atmosphere for kite surfing, a popular sport in Kailua.

2. Location

Photographs don't do justice to the natural beauty of Kailua and the surrounding communities. Towering waterfalls, frequent rainbows, mountainous peaks, and colorful ocean reefs are just a few of the undeniably astounding highlights of living in Kailua.

The Pali Highway and the Likelike Highway provide easy access to the rest of the island, allowing for a simple 25-minute commute to Waikiki. The Daniel K. Inouye International Airport in Honolulu is only 30 minutes away, making traveling to other Hawaiian islands and the mainland a breeze.

The most common mode of transportation is a moped or bicycle for getting around town and avoiding traffic, which tends to back up during the peak tourist season. The weather is mild, averaging 85°F in summer (May to October) and 78°F in winter (November to April). Regardless of the time of year, there is always sunshine.

3. Kaneohe Yacht Club

Since 1924, the Kaneohe Yacht Club has been helping islanders enjoy maritime sports, powerboating, and sailing by providing recreational, social, and competitive activities. It offers first-class harbor facilities, a luxurious clubhouse, an open-air longhouse, fabulous dining options, and a host of amenities to encourage the overall spirit of excellence and camaraderie in the boating community of Windward Oahu.

4. World-class golf courses

Hawaii has a long history of first-class golf, with world-renowned courses scattered throughout the island, offering breathtaking vistas and unique features. Listed below are the two championship greens and Oahu's military base golf course.

Mid-Pacific Country Club

This private oceanfront club offers a first-class golf course with incredible views of the iconic Mokulua Islands and Ko'olau Mountains. Since 1926, Mid-Pacific Country Club has hosted some of the world's finest golfers. Membership is by invitation only and includes exclusive access to the course and all clubhouse facilities, social events, and services. A fully equipped fitness center provides complimentary wellness classes and a swimming pool where members can relax after a day on the links.

Royal Hawaiian Golf Club

The lush fairways of the Royal Hawaiian Golf Club overlook the majestic Ko'olau and Olomana mountains. Recently redesigned by pro golfer Greg Norman, the par-72 course offers meticulously manicured greens for a one-of-a-kind experience. The 45,000-square-foot clubhouse includes upscale amenities, including locker and shower facilities and delicious regional cuisine served in The ‘Olena dining room.

Kaneohe Klipper Golf Course

Located on the U.S. Marine Corps Base, the 18-hole Kaneohe Klipper Golf Course is regarded as the world's best military golf course. Offering spectacular views of the Pacific Ocean and Koolau Mountains, this peaceful haven is only for military personnel, families, and authorized guests.

5. First-rate amenities

Despite being located in a peaceful section of the island, Kailua still provides a wide assortment of excellent amenities, including trendy eateries, chic boutiques, fitness centers, health food stores, and bakeries.

There is even a Target and Whole Foods for modern conveniences, and at the weekly farmers’ market, residents have access to delicious fresh fruits, such as juicy pineapples and ripe mangoes. The nearby Adventist Health Castle Hospital provides top-quality medical care.

Cons of living in Kailua

While Kailua is idyllic, it isn't perfect. There are a few things to consider before deciding if island life is right for you.

1. Cost of living

Living in Kailua is not all sunshine and rainbows. According to World Population Review Rankings, Hawaii has the highest cost of living in the country. Over the past few years, the state has experienced a declining population as many residents are moving to the mainland seeking a more affordable lifestyle.

According to the Honolulu Board of Realtors®, the median price for a single-family home in Oahu is more than $1.08 million, making home ownership difficult for many residents. Rental rates and overall housing costs are at an all-time high, and with the limited availability of luxury properties in Kailua, there is fierce competition in the housing market.

2. Tourist season

Living in a top vacation destination can be challenging, with more than 9.2 million visitors traveling to Hawaii annually.

During peak tourist season, which runs from December through April, the island swells with visitors from around the world. According to the Department of Business Economic Development and Tourism, visitor spending amounted to $19.3 billion in 2022. With tourism being Hawaii's largest industry, the economy depends on the money these travelers bring. However, that doesn't make the traffic, long lines, noisy restaurants, and crowded beaches any easier. Many locals avoid driving during the busiest times of day to avoid the gridlock and choose to stay in their local communities when tourism is at its peak.

3. Island fever

Vacationing on an island is much different than living on one. Many new residents to Oahu don't realize how small the island is until they have spent a few months visiting the same shops, cafes, and local establishments.

Most places close by 10 pm, so there is little nightlife. Most locals prefer rising with the sun to hit the surf early. If you are a night owl and like a vibrant club scene, this could present a problem. Some people also find it challenging to assimilate into the local community, with long-time residents known for keeping newcomers at a distance. While most locals are friendly, many families have lived on the island for generations, and not being part of that heritage can sometimes feel off putting.

Fortunately, a quick trip to another island or back to the mainland for a change of scenery can dissipate negative feelings, reminding you of all the reasons you love living in Kailua.

Contact Scott Steiner to learn more about the pros and cons of living in Kailua

Whether you are looking for a laidback lifestyle with a beach town vibe or searching for a fabulous new location to call home, Kailua may be the place for you. Contact Scott Steiner, an experienced real estate agent familiar with the area and all it offers. He can answer any questions you may have and show you around the island, helping to make your dream of living in Kailua a reality.

*Header photo courtesy of Shutterstock


Being born and raised in Kailua, a Punahou Alumni, and seventh generation Kama’aina, he has a unique perspective on the value of Real Estate here on Oahu. His personal insight to Oahu’s unique market is unmatched. Contact him today so he can guide you through the buying and selling process.

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