Kailua Vacation Rentals

Our Favorite Vacation Rentals in Kailua (Oahu)

  • Comfortable 3 bedroom two bathroom unit
     Home/Apartment
    Booking.com
    From
    $168
  • Sheffield Studio Walk to Kailua Beach or Town
    GoodStudio
    HolidayLettings
    From
    $232
  • The Ritz-Carlton Residences, Waikiki Beach
     Home/Apartment
    NextTrip
    From
    $676
  • Oceanside Villa
     Country House
    Booking.com
    From
    $483
  • Tropical Ocean Views Mansion
     4br Home/Apartment
    HolidayLettings
    From
    $3,288
  • High floor convenient and spacious 2BR 1BA Wifi
     Home/Apartment
    Booking.com
    From
    $230
  • Blue House Studios in Lovely Manoa Valley
    NiceHome/Apartment
    HolidayLettings
    From
    $147
  • Downtown 2BR+Den free parking+Wifi AC Ocean Views
     Home/Apartment
    Booking.com
    From
    $250

Check prices for these upcoming dates

Kailua (Oahu) Vacation Rentals with a Pool

  • Honeymoon beachfront luxury private villa
     2br Home/Apartment
    Airbnb
    From
    $1,898
  • Vintage Aloha Oceanside Suite
    ExcellentHome/Apartment
    Airbnb
    From
    $237
  • Mountain View Pool Cottage in Hawaiian Valley
    ExcellentHome/Apartment
    Airbnb
    From
    $139
  • Beachfront home away from home
     5br Home/Apartment
    Airbnb
    From
    $2,486

Kailua (Oahu) Vacation Rentals with Wi-Fi

  • Tropical 2Brs house private access to the beach
     2br Home/Apartment
    Airbnb
    From
    $1,286
  • Oceanfront Luxury private villa with gorgeous pool
     11br Home/Apartment
    Airbnb
    From
    $12,701
  • GORGEOUS 3Bed 2Bath in KAILUA w/ AC!!!
    Excellent3br Home/Apartment
    Airbnb
    From
    $509
  • Kailua Bungalow Airy and Bright 2, Oahu
    ExcellentBungalow
    Airbnb
    From
    $128

Kailua (Oahu) Pet-Friendly Vacation Rentals

  • [MOKES]-Beachfront Luxury private villa premium
     8br Home/Apartment
    Airbnb
    From
    $5,158
  • DESIGNER VILLA WITH PANORAMIC OCEAN VIEW
     6br Home/Apartment
    Airbnb
    From
    $831
  • Welcoming House in Center of Everything 2
    Excellent3br Home/Apartment
    Airbnb
    From
    $264
  • Hawaiian Oasis near Waikiki & more
    Good3br Home/Apartment
    Airbnb
    From
    $678

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
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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 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 Weather in Kailua (Oahu)

Rainy days
85° 67°
6
82° 65°
2
85° 66°
1
84° 62°
6
84° 64°
2
87° 63°
4
83° 65°
3
86° 73°
1
86° 73°
1
87° 71°
1
90° 70°
6
87° 71°
7
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Kailua (Oahu). The hottest month in Kailua (Oahu) is April, when temperatures peak at 90 ˚F. The coolest month is November, when temperatures drop to 62 ˚F. The wettest month in Kailua (Oahu) is March with 6.53 inches of rain, while the driest month is July with 0.66 inches of rain.

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