Kailua, HI Vacation Rentals: house rentals & more

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 $88 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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Find the best place to stay — Kailua

Search 3,152 vacation rentals

Stayed Oct 2020

Wonderful Escape & Work Vacation

We had an excellent one month stay for our remote work vacation. The house is beautiful, well-furnished, clean, and in a terrific location being so close to Kailua beach and Lanikai. Diana and Rudy were wonderful hosts. With several us needing to be ...

Stayed Oct 2020

Nice and quiet :)

I'm really glad that I found this place. I have hours during the day that I have to work online so it's nice that is quiet around. I know the owners, which is very fortunate, because they're ones of the nicest people I know. This place is like super ...

Stayed Aug 2020

Amazing time in paradise

We stayed here for 6 weeks in August/September 2020, and it was an incredible time. We spent almost all our hours in the backyard, hanging out and swimming and enjoying the scenery. The location was great and super close to a beautiful beach (<5 ...

Stayed Jul 2020

Wonderful Staycation

I loved this studio! Not only was the location perfect, the property itself was relaxing, beautiful, and was stocked with almost every amenity you could think of. I am from Kailua originally, and would definitely recommend a stay here. I really enjoy...

Stayed Apr 2020

Paradise

This adorable home is in an incredible location across from the most beautiful beach. It’s the perfect place for families, our 6 and 8 year old had the best time playing in and exploring the massive yard. The owners and house manger are so kind and a...

Stayed Mar 2020

This place was so cute & perfect

We felt 100% at home in this SUPER CUTE cottage. Adorable and VERY clean. In a safe, friendly neighborhood. We walked downtown 1 night and could have walked to the beach too. Cindy was helpful with dinner and hiking suggestions. This place is a winne...

Stayed Mar 2020

Kailua beach house

We had a wonderful vacation in Herman’s home. It had every amenity we needed. The pictures and location does not do it justice. It was perfect, beautiful and very clean. Herman was quick to respond to our inquiries. We would definitely stay here agai...

Stayed Mar 2020

Spectacular Place to Stay

My husband and I had such a wonderful time on our babymoon! The location cannot be beat - we loved being just a few minutes from the best beach on the island (Kailua beach). We were far enough away from the hustle and bustle of the bigger city but cl...

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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 2020 property listings offer a large selection of 3,152 vacation rentals around Kailua. From 445 house rentals to 51 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: 151 vacation rentals
Kalama Tract: 167 vacation rentals
Enchanted Lake: 234 vacation rentals
Coconut Grove: 176 vacation rentals
Keolu Hills: 182 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: 3,251 vacation rentals
Kaneohe Klipper Golf Course: 3,310 vacation rentals
Lanikai Pillboxes Trailhead: 3,230 vacation rentals
Mokapu Point: 3,280 vacation rentals
Kawainui Park: 3,289 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 445 Houses in Kailua. Our other popular types of vacation rentals in Kailua include:

Cottages: 51 rentals available
Condos/Apartments: 2,036 rentals available
Villas: 32 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 1,982 vacation rentals with pool available in Kailua. Please use our search bar to access the selection of vacation rentals available.