Kailua Vacation Rentals

Our Favorite Vacation Rentals in Kailua (Oahu)

Fairway Villa 1803 Apartment

RedAwningFrom $307
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holiday apartment for max. 16 persons in Kailua, Hawaii

TUIVillasFrom $35388
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Brand new private room
Good
Booking.comFrom $67
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Nice cozy studio3, Enchanted Lake Kailua

HolidayLettingsFrom $199
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Waikiki Banyan - Walk to the Beach

NextTripFrom $296
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Palms Waikiki 506

RedAwningFrom $315
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holiday home for max. 14 persons in Honolulu, Hawaii

TUIVillasFrom $12192
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East side of Hanama Bay, Diamond Head
Good
Booking.comFrom $79
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Kailua (Oahu) Vacation Rentals with a Pool

Waikiki Sand Villa Hotel

NextTripFrom $189
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Hilton Hawaiian Village Waikiki Beach Resort

NextTripFrom $528
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Aloha Surf Condominium 1412

RedAwningFrom $294
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Hilton Grand Vacations At Hilton Hawaiian Village

NextTripFrom $389
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Kailua (Oahu) Vacation Rentals with Wi-Fi

Diamond Head Beach Hotel 801

RedAwningFrom $499
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Aloha Surf Apartment #1209

RedAwningFrom $294
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Aloha Surf 1509

RedAwningFrom $250
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Aloha Surf 207

RedAwningFrom $200
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Kailua (Oahu) Pet-Friendly Vacation Rentals

Just 5 minutes away from beautiful Kailua Beach

FlipkeyFrom $897
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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 in Kailua (Oahu)

Most expensive

Most availability

The most expensive month to stay in a vacation rental in Kailua (Oahu) is in July, while the cheapest month is in September. The most popular time to book a vacation rental in Kailua (Oahu) is in the high season in July. 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 Sunday, while the most expensive day tends to be Tuesday. Vacation homes in Kailua (Oahu) tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Kailua (Oahu)

SEE FULL WEATHER FORECAST:

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

84º 64º

2.46

87º 63º

4.14

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

Rainy days

SEE FULL WEATHER FORECAST:

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

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Middle Class Dad
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Vacation Rentals in Kailua (Oahu)

Browse rentals from all the leading providers including Airbnb, VRBO, Homeaway and many more at AllTheRooms.com. Kailua (Oahu) has 698 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, extravagant travelers and everything in between. For those trying to save money, the lowest priced place to stay in Kailua (Oahu) comes in at $45 a night. On average, a place to stay in Kailua (Oahu) will cost you $576 per night.

Those needing to get some work done during their trip to Kailua (Oahu) can choose from 610 places to stay that include WiFi. We have 4 accommodations that come with breakfast included. Fitness addicts can get a workout in during their stay by choosing from 22 accommodations that have gym facilities. If you are driving to Kailua (Oahu), you'll want to pick from 594 places to stay that provide parking. 80 hotels and vacation rentals come with a pool or jacuzzi

Those traveling with a dog, cat or some other animal can stay in one of 33 accommodations that are designated as pet-friendly.

We combine a wide variety of Kailua (Oahu) accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 5 providers, including 288 places to stay from Airbnb, 278 accommodations from VRBO and 45 places to stay from Homeaway.

629 of our rentals in Kailua (Oahu) have been reviewed by previous guests. They rated 87% as great. 257 places to stay in are instantly bookable.