Kailua vacation rentals

We found 4,643 vacation rentals — enter your dates for availability

your current months are September, 2023 and October, 2023.
September 2023
October 2023
Select from 186 houses, 59 apartments, and other vacation rentals to find the perfect place for your stay in Kailua. Vacation rentals provide the best amenities for your family, friends, or furry companion, like air conditioning and WiFi. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Delight in the waterfront landscape of Kailua

The island views and surrounding scenery provide a peaceful ambiance to your vacation home in Kailua. This city's kayaking, coral reefs and hiking draw many visitors. There are plenty of places to find the perfect souvenir including Ala Moana Center, Waikiki Beach Walk and International Market Place. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Kailua

Do you want to find attractions to visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Kailua a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Ala Wai Golf Course (10 mi / 16.2 km)
  • Honolulu Zoo (10.4 mi / 16.8 km)
  • Kaneohe Klipper Golf Course (3.4 mi / 5.5 km)
  • Ko'olau Golf Club (3.6 mi / 5.8 km)
  • Waialae Country Club (9.4 mi / 15.1 km)
  • Mamala Bay Golf Course (13.9 mi / 22.3 km)

Exploring the beaches and other natural features in Kailua

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Kailua. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Waikiki Beach (10.4 mi / 16.8 km)
  • Pearl Harbor (15.3 mi / 24.6 km)
  • Kalama Beach Park (0.2 mi / 0.3 km)
  • Kailua Bay Beach (0.8 mi / 1.2 km)
  • Kailua Beach (0.9 mi / 1.4 km)
  • Lanikai Beach (1.7 mi / 2.7 km)

Seasonal weather averages in Kailua

Travelers enjoy Kailua for its snorkeling. If you're planning a vacation around warm-weather activities, September, August, October and July are the hottest months to visit, when temperatures average 79°F.

Transportation to and around Kailua

The nearest airport is in Daniel K. Inouye Intl. Airport (HNL), located 12.6 mi (20.2 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Kapolei, HI (JRF-Kalaeloa), which is 22.2 mi (35.7 km) away.