Kailua, HI, US Vacation Rentals: house rentals & more

Discover a selection of 4,000 vacation rentals in Kailua, HI, US 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 pool and air conditioning. Prices start at C$ 219 per night, and house rentals and condo and apartment rentals 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 4,478 vacation rentals

Stayed Jun 2022

Location and comfort, the total package.

Location can't be beat! 30 seconds to one of the most beautiful beaches in the world. Lots of room for two and a great layout. It was really nice having a king size bed too. Easy to find and good parking. Our host was very friendly and super knowledg...

Stayed Jun 2022

Awesome ocean front!

Clean and quaint and right on the beach! Many Kailua rentals while pricey are still run down and moldy. The host of this rental is amazing and keeps the rental unit in tip top shape. Convenient location, 5 minute drive into Kailua or walk the beach t...

Stayed May 2022

The best!

I’ve stayed at at least eight places in Kailua, and this was the best by far—easily walkable to the beach and town, beautiful and quiet property, friendly owner, comfortable bed, fresh fruit provided, toaster oven and microwave and refrigerator for l...

Stayed May 2022

Great location on Oahu

We really enjoyed our stay here. Great, quiet location that is removed from the hustle and bustle of Oahu, but still just a short drive to the major hubs. Beautiful beach right across the street. We knew we had an efficiency and only planned to cook...

Stayed May 2022

Kailua Gem

My husband and I rented for a week in May. Everything about the rental was wonderful for us. It was quiet, beautiful view of water, sunrises and sunsets, kayaks on the lake, close to shopping and downtown Kailua, close to beaches, including beautiful...

Stayed May 2022

Absolutely wonderful

The property and homeowner (Leonard) were absolutely wonderful. Everything was clean, cozy, and comfortable. Leonard was a delight to talk to. We were a 7 minute walk to the beautiful Kailua beach and 5 minutes from shopping, grocery stores, and tast...

Stayed May 2022

May 2022 two week vacation

Luke and Robin have a beautiful, confidently located home in Kailua. We were a few blocks from Kalama Beach, which didn’t get packed like Kailua and Lanikai beach did. However, it was so close I took a walk from their home to Kailua beach while Mike ...

Stayed May 2022

A perfect place for us!

We have stayed at several guest houses in Kailua, and this one quickly rose to the top of our list of favorites. A well planned and furnished space with everything we needed plus private access to Kailua Beach - a perfect place to watch the day begin...

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How many vacation rentals are available around Kailua?

Our 2022 vacation rental listings offer a large selection of 4,478 house rentals around Kailua. From 464 house rentals to 2,634 condo and apartment rentals, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Kailua is on Vrbo.

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

Whether you're travelling 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: 154 vacation rentals
Kalama Tract: 159 vacation rentals
Enchanted Lake: 234 vacation rentals
Coconut Grove: 168 vacation rentals
Keolu Hills: 184 vacation rentals

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

What are the popular points of interest near where I can stay when travelling to Kailua?

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

Lanikai Pillboxes Trailhead: 4,416 home rentals
Kawainui Park: 4,427 home rentals
Kaneohe Klipper Golf Course: 4,456 home rentals
Mokapu Point: 4,420 home rentals
Royal Hawaiian Golf Club: 4,405 home rentals

But there are many other points of interest around Kailua listed on Vrbo Canada 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.