Kailua Vacation Rentals

Our Favorite Vacation Rentals in Kailua (Oahu)

  • Aloha Surf Condominium 1412
     Home/Apartment
    RedAwning
    From
    $297
  • Tropical Studios at Marine Surf Waikiki
     Home/Apartment
    Booking.com
    From
    $189
  • Luxury home(s) just steps away from Kailua Beach
     4br Home/Apartment
    HolidayLettings
    From
    $1,710
  • Palms Waikiki 320 Studio
     Home/Apartment
    RedAwning
    From
    $305
  • Tropical Ocean Views Mansion
     4br Home/Apartment
    HolidayLettings
    From
    $3,288
  • WB2801-Waikiki 201 Ohua Ave Honolulu 1 DLDL-PTO-00-CHK
     Home/Apartment
    RedAwning
    From
    $419
  • Large Cozy Studio near Shopping Centers
     -1br Studio
    HolidayLettings
    From
    $119
  • Diamond Head Beach Hotel 501
     2br Home/Apartment
    RedAwning
    From
    $649

Check prices for these upcoming dates

Kailua (Oahu) Vacation Rentals with a Pool

  • Aloha Surf 207
     Home/Apartment
    RedAwning
    From
    $229
  • AS1205 444 Kanekapolei St Honolulu TH-PTO-00-ACH
     Home/Apartment
    RedAwning
    From
    $300
  • Aloha Surf 610 Apartment
     Home/Apartment
    RedAwning
    From
    $255
  • Hawaiian King 405 Apartment
     Home/Apartment
    RedAwning
    From
    $310

Kailua (Oahu) Vacation Rentals with Wi-Fi

  • MS608 THTH-CTOQ(MA)-00-ACH
     Home/Apartment
    RedAwning
    From
    $341
  • BB809 2425 Kuhio Ave Honolulu DLDL-CTOQ(TC)-MFLH-ACH
     Home/Apartment
    RedAwning
    From
    $306
  • Bamboo 801 Condominium
     Home/Apartment
    RedAwning
    From
    $295
  • Bamboo 301 Apartment
     Home/Apartment
    RedAwning
    From
    $279

Kailua (Oahu) Pet-Friendly Vacation Rentals

  • Waikiki - Minutes from beach upto 6 people
    GoodHome/Apartment
    Flipkey
    From
    $335
  • Waterfront pool house paddle to beach
     4br Home/Apartment
    Airbnb
    From
    $1,580
  • Oceanfront Luxury private villa with gorgeous pool
     11br Home/Apartment
    Airbnb
    From
    $12,633
  • *LANI KAI"--Beachfront Hawaiia luxury villa w/pool
     5br Home/Apartment
    Airbnb
    From
    $3,367

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
82° 63°
1
82° 59°
4
83° 63°
1
85° 66°
3
87° 67°
2
86° 70°
4
82° 71°
1
94° 66°
1
89° 76°
2
89° 72°
7
88° 66°
2
84° 67°
4
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Kailua (Oahu). The warmest months in Kailua (Oahu) are May and March, when temperatures reach 94 ˚F. The coolest month is November, when temperatures drop to 59 ˚F. The wettest month in Kailua (Oahu) is March with 6.68 inches of rain, while the driest month is October with 0.8 inches of rain.

What Expert Travelers Think

  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum

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