Discover a selection of 3,000 vacation rentals in Kailua, HI that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $175 per night, and houses and cottages are popular options for a stay in Kailua. Either way, you'll find a rental for everyone's needs.
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Destination guide

The laid-back Kama’aina lifestyle in Kailua

Called Kailua Town by residents, Kailua is a buzzing beach community where a laid-back lifestyle is the rule. If turquoise water and white sand on Oahu’s windward coast aren’t enough for you, jump into trendy boutiques, stop off at popular eateries, and hang out with the kama’aina (locals) at the Thursday evening farmers’ market. Distinctive ingredients put a twist on the island cuisine here, and unique boutiques offer treasures to commemorate your stay in any one of the Kailua vacation rentals.

Things to do

An Aloha adventure in Kailua

Water is the watchword here, and Lanikai Beach or Kalama Beach Park, the Kawai Nui Marsh wetlands, or Maunawili Falls may just float your boat. From stunning sunrises to spectacular sunsets, the 1-mile Lanikai Pillbox hike offers a sweeping panoramic view of land and sea from concrete bunkers, built between WWI and WWII as part of Oahu’s coastal defense system. And, within a stone’s throw of the shore, Moku Nui, Moku Iki, and Flat Island are a meditative mantra to while away the hours on the silky soft sand of Kailua Beach. Experience all the warmth and hospitality of the Aloha spirit at family-friendly Kailua vacation rentals.

Activities

Land and sea is all you need in Kailua

Surf, kitesurf, windsurf, or kayak are the best ways to explore this area. Kailua Beach is a reef-protected bay where beauty and safety reign supreme, so swimming and snorkeling are stress-free. Head out for a hike or a round of golf in this lush, green paradise. Take a picnic blanket, and enjoy local favorites as you listen to live music at the Kailua Farmers’ Market. If you’re a fan of the slower island pace, Kailua has the small-town vibe that delivers an authentic Hawaiian experience. Kailua vacation rentals offer the calm you crave and the family fun you want.

Weather

A tropical paradise in Kailua

With an annual average temperature of 71°F, inching up to 80 or so in summer, any season is a good time to visit Kailua. Lush and tropical, passing showers in winter months won’t dissuade you from hanging loose under the sun, and coastal trade winds will temper any high humidity in summer. Keep in mind that high season in Hawaii runs from mid-December through March or mid-April, since snowbirds from colder climes like to wing their way to paradise at that time, though Kailua is still somewhat of an Oahu hideaway.

Natural features

Kailua—a natural beauty

Located on the leeward side of the Nu’uanu Pali peak, crescent-shaped Kailua Bay is sheltered from the hustle and bustle of Honolulu. Crystal blue water and silky white sand invite visitors to come and stay awhile. Meaning heavenly sea in Hawaiian, Lanikai Beach is another mile-long stretch that is a favorite of many locals. Once the center of life for early Kailuans, the Kawai Nui Marsh is a protected wetland, providing a habitat to many wildlife species, and a peaceful trail. Hike in Maunawili Falls are the most accessible in Oahu and cascade 15 to 30 feet into a cool mountain pool.

How to get there

Transportation to and around Kailua

The nearest airport is in Honolulu, HI (HNL-Daniel K. Inouye Intl.), located 12.5 mi (20.1 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Kapolei, HI (JRF-Kalaeloa), which is 22.2 mi (35.7 km) away.

How many vacation rentals are available around Kailua, HI?

Our 2021 property listings offer a large selection of 2,843 vacation rentals around Kailua. From 375 house rentals to 40 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Kailua?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Kailua:

  • Lanikai: 128 vacation rentals
  • Kalama Tract: 145 vacation rentals
  • Enchanted Lake: 201 vacation rentals
  • Coconut Grove: 153 vacation rentals
  • Keolu Hills: 155 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Kailua?

Vrbo offers a large selection of vacation rentals near lovely places in Kailua. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Royal Hawaiian Golf Club: 2,903 vacation rentals
  • Kaneohe Klipper Golf Course: 2,959 vacation rentals
  • Lanikai Pillboxes Trailhead: 2,884 vacation rentals
  • Mokapu Point: 2,952 vacation rentals
  • Kawainui Park: 2,950 vacation rentals

But there are many other points of interest around Kailua listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Kailua?

Yes, of course. Vrbo has 375 Houses in Kailua. Our other popular types of vacation rentals in Kailua include:

  • Cottages: 40 rentals available
  • Condos/Apartments: 1,942 rentals available
  • Villas: 29 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Kailua?

Yes, you can select your preferred vacation rental with pool among our 1,776 vacation rentals with pool available in Kailua. Please use our search bar to access the selection of vacation rentals available.