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Kailua Vacation Rentals

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Our Favorite Vacation Rentals in Kailua (Oahu)

See all 704 deals in Kailua (Oahu)

Kailua (Oahu) Vacation Rentals with a Pool

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Kailua (Oahu) Vacation Rentals with Wi-Fi

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Kailua (Oahu) Pet-Friendly Vacation Rentals

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Kailua Oahu Travel Guide

This Hawaiian paradise town is perfect for any beach lover’s vacation. The town is known as a resort town on the island of Oahu along the shore. Hawaii’s picturesque beaches have clear turquoise waters and soft white sand, as well as excellent surf or swim spots up and down the coast. Top beaches in Kailua include Lanikai Beach, ranked as one of the best beaches in the world, and Kailua Beach, once ranked as the number one beach in the United States.

Things to Do in Kailua Oahu

Hike the Lanikai Pillbox Trail or the Kaiwa Ridge Trail to get the best views of the ocean all around. The Maunawili Falls Trail is another popular hiking spot in town. The 2.5-mile trail leads you to the stunning swimming hole and scenery at Maunawili Falls. The Kailua Farmer’s Market is something you truly can’t miss for all the locally grown fruits and veggies, as well as the handmade souvenir crafts.

Best Time to Visit Kailua Oahu

Hawaii is beautiful and warm all year round, but the best time to visit Kailua is from January through May. Kailua is full of sleepy, relaxed beach town vibes all around. Locals in town are relaxed and open-minded, and most residents work hard to preserve the environment and local culture.

Price and Availability Index in Kailua (Oahu)

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The most expensive month to stay in a vacation rental in Kailua (Oahu) is in July, while the cheapest month is in October. The most popular time to book a vacation rental in Kailua (Oahu) is in the high season in February. Kailua (Oahu) has its low season in September, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Kailua (Oahu) tends to be Thursday, while the most expensive day tends to be Saturday. Vacation homes in Kailua (Oahu) tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.

The Weather in Kailua (Oahu)

84º 64º
2.46
87º 63º
4.14
83º 65º
2.81
86º 73º
0.66
86º 73º
0.74
87º 71º
1.46
90º 70º
5.55
87º 71º
6.53
85º 67º
5.85
82º 65º
1.78
85º 66º
1.37
84º 62º
6.2
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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Dec
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Feb
Rainy days
This climate histogram shows you the weather patterns in Kailua (Oahu). The warmest months in Kailua (Oahu) are April and September, when temperatures reach 90 ˚F. The coolest month is February, when temperatures drop to 62 ˚F. The wettest month in Kailua (Oahu) is October with 6.53 inches of rain, while the driest month is June with 0.66 inches of rain.

What Expert Travelers Think

Vacation Rentals in Kailua (Oahu)

At AllTheRooms.com we have accommodations from all of your favourite providers - Airbnb, VRBO, Homeaway and more. AllTheRooms has 704 vacation rentals, hotels and other great places to stay during your time in Kailua (Oahu), with everything from cheap hostels and homestays to luxury Airbnbs and hotels. For those traveling on a budget, the cheapest place to stay in Kailua (Oahu) is available at $45 per night. On average, a place to stay in Kailua (Oahu) will cost you $583 per night.

Those looking to get some work done during their trip to Kailua (Oahu) can pick from 617 places to stay that provide WiFi. 4 of our accommodations in include a breakfast in the price. Choose from 23 places to stay that provide gym facilities, so you won't miss a single workout. Driving to Kailua (Oahu)? Then choose one of the 601 places to stay that comes with a parking spot included. 81 hotels and vacation rentals have a pool or jacuzzi.

If you're traveling with a furry friend, then be sure to choose one of the 34 pet-friendly accommodations available.

AllTheRooms aggregates vacation rentals, hotels and other unique accommodation types from 5 providers in Kailua (Oahu), including 287 places to stay from Airbnb, 285 accommodations from VRBO and 46 places to stay from Homeaway

633 accommodations in Kailua (Oahu) have been reviewed: 83% are rated excellent or good. 280 places to stay in are instantly bookable.

Destinations near Kailua (Oahu)

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