We found 2,952 vacation rentals — enter your dates for availability
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 $180 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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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 2,952 vacation rentals around Kailua. From 372 house rentals to 39 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: 131 vacation rentals
- Kalama Tract: 157 vacation rentals
- Enchanted Lake: 210 vacation rentals
- Coconut Grove: 166 vacation rentals
- Keolu Hills: 158 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: 3,190 vacation rentals
- Kaneohe Klipper Golf Course: 3,242 vacation rentals
- Lanikai Pillboxes Trailhead: 3,171 vacation rentals
- Mokapu Point: 3,215 vacation rentals
- Kawainui Park: 3,208 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 372 Houses in Kailua. Our other popular types of vacation rentals in Kailua include:
- Cottages: 39 rentals available
- Condos/Apartments: 1,962 rentals available
- Villas: 28 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 1,821 vacation rentals with pool available in Kailua. Please use our search bar to access the selection of vacation rentals available.