Kailua Vacation Rentals

Our Favorite Vacation Rentals in Kailua (Oahu)

  • AS1209 444 Kanekapolei St Honolulu TH-CTOQ(JCa)-00-ACH
     Home/Apartment
    RedAwning
    From
    $278
  • Diamond Head Duplex Duplex
     Home/Apartment
    Booking.com
    From
    $256
  • The quaint Kailua-Kalama "Cottage"
    ExcellentCottage
    HolidayLettings
    From
    $192
  • Palms Waikiki 320 Studio
     Home/Apartment
    RedAwning
    From
    $305
  • Paradise Beach Estate
     Villa
    Booking.com
    From
    $2,500
  • Renovated 1bd/1bath near Chinaman's Hat & Valley of the Temples
    GoodHome/Apartment
    HolidayLettings
    From
    $126
  • WB2513 Waikiki 201 Ohua Ave Honolulu DLDL-CTOQ(DM)-00-CHK
     Home/Apartment
    RedAwning
    From
    $415
  • Ke Mele studio
     Home/Apartment
    Booking.com
    From
    $99

Check prices for these upcoming dates

Kailua (Oahu) Vacation Rentals with a Pool

  • Aloha Surf 207
     Home/Apartment
    RedAwning
    From
    $227
  • Aloha Surf 610 Apartment
     Home/Apartment
    RedAwning
    From
    $255
  • AS1205 444 Kanekapolei St Honolulu TH-PTO-00-ACH
     Home/Apartment
    RedAwning
    From
    $257
  • Aloha Surf 1507 Condominium
     Home/Apartment
    RedAwning
    From
    $235

Kailua (Oahu) Vacation Rentals with Wi-Fi

  • Diamond Head Beach Hotel 1104
     Home/Apartment
    RedAwning
    From
    $297
  • Hawaiian King 405 Apartment
     Home/Apartment
    RedAwning
    From
    $302
  • BB809 2425 Kuhio Ave Honolulu DLDL-CTOQ(TC)-MFLH-ACH
     Home/Apartment
    RedAwning
    From
    $266
  • Bamboo 301 Apartment
     Home/Apartment
    RedAwning
    From
    $279

Kailua (Oahu) Pet-Friendly Vacation Rentals

  • DISCOUNTED Aug/Sept! Trendy+Spacious House w/ Pool
    Excellent2br Home/Apartment
    Airbnb
    From
    $305
  • [KAI LUA]-Luxury beachfront original Hawaiian pool
     5br Home/Apartment
    Airbnb
    From
    $2,848
  • MODERN HOME minutes from LANIKAI
     4br Home/Apartment
    Airbnb
    From
    $605
  • Home is Where you Park it
     Home/Apartment
    Airbnb
    From
    $211

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
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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
90 º70
6
87 º71
7
85 º67
6
82 º65
2
85 º66
1
84 º62
6
84 º64
2
87 º63
4
83 º65
3
86 º73
1
86 º73
1
87 º71
1
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Kailua (Oahu). The warmest months in Kailua (Oahu) are April and March, when temperatures reach 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.

What Expert Travelers Think

  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae
  • — 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
  • — 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

Destinations near Kailua (Oahu)

  • Kailua-Kona6,666 Properties
  • Princeville5,755 Properties
  • Honolulu4,836 Properties
  • Kaanapali4,624 Properties
  • Wailea3,832 Properties
  • Lahaina3,545 Properties
  • Kamuela2,860 Properties
  • Kihei2,770 Properties
  • Waikoloa2,574 Properties
  • Kapaa2,391 Properties
  • Kapalua1,913 Properties
  • Koloa1,737 Properties
  • Kahuku1,445 Properties
  • Volcano1,383 Properties
  • Maalaea1,271 Properties
  • Hilo1,191 Properties
  • Pahoa1,190 Properties
  • Captain Cook933 Properties
  • Wailua838 Properties
  • Lihue804 Properties
  • Keaau756 Properties
  • Kapolei540 Properties
  • Hauula517 Properties
  • Hanalei517 Properties
  • Haleiwa510 Properties
  • Maunaloa448 Properties
  • Laie381 Properties
  • Waialua329 Properties
  • Kaunakakai325 Properties
  • Waimanalo317 Properties
  • Waianae310 Properties
  • Ewa Beach264 Properties
  • Paia196 Properties
  • Wailuku158 Properties
  • Haiku156 Properties
  • Hawi129 Properties
  • Kaneohe124 Properties
  • Hakalau120 Properties
  • Hana111 Properties
  • Kekaha103 Properties
  • Mokuleia100 Properties
  • Kilauea92 Properties
  • Kahului91 Properties
  • Holualoa77 Properties
  • Honokaa74 Properties
  • Waipahu61 Properties
  • Mililani41 Properties
  • Waimea28 Properties