Kailua vacation rentals

We found 81 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Scroll through and select from vacation rentals in Kailua to find one that's perfect for your trip. Vacation homes provide the best amenities for your stay with friends, family, or just your pet, like air conditioning and cable TV. At the end of the day, you'll find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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

Book a vacation rental for your Kailua getaway

Experience the unique character of Kailua with a stay in a vacation home rental. There's no shortage of things to see and do in the area.Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Kailua

Are you looking for things to do while you're in town? Venture out of your vacation home and experience everything that makes Kailua a one-of-a-kind vacation spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Ho'omana Spa Maui (6.6 mi / 10.6 km)
  • Haleakala Bike Company (6.9 mi / 11.2 km)
  • Maui Spa Retreat (7.8 mi / 12.5 km)
  • Pukalani Country Club (9.5 mi / 15.3 km)
  • King's Highway (15.8 mi / 25.4 km)
  • Enlighten Up Massage (7.4 mi / 11.9 km)

Exploring the natural features in Kailua

Whether you're an outdoor enthusiast or just want to take in the scenery, Kailua is a great place to get out in nature. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Twin Falls (2 mi / 3.2 km)
  • Maui Garden Of Eden - Botanical Gardens & Arboretum (3.2 mi / 5.1 km)
  • Haiku Park (7.3 mi / 11.8 km)
  • Hookipa Beach Park (9.5 mi / 15.3 km)
  • Kuau Bay Beach (10 mi / 16.1 km)
  • H.A. Baldwin Beach State Park (11.2 mi / 18 km)

How to get to and around Kailua

The nearest airport is in Kahului Airport (OGG), located 14.3 mi (22.9 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Hana, HI (HNM), which is 14.8 mi (23.9 km) away.

Frequently asked questions

How much does it cost to rent a vacation rental in Kailua?

The average price for a vacation rental in Kailua depends on a number of factors, such as property type, season and length of stay. Whether you're searching for a sprawling house with room for friends and family or a quaint cabin that's perfect for two, just add your dates of travel to see some great-value stays.

How much does it cost to rent a beach house in Kailua?

When you travel and the style and size of the property will influence how much you'll pay for your beachside vacation rental. Put in your Kailua travel dates to view your available options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the amenities and features you want.

What are the top attractions for families in Kailua?

Treat the kids to a good time at these cool family-friendly attractions in Kailua:

  • Twin Falls
  • Haiku Park

How old do you have to be to rent a vacation rental in Kailua?

We advise checking with the Kailua vacation property you're considering on Vrbo as the age limit differs. However, generally it's 16, 18 or 21.

How long can I rent a vacation rental in Kailua for?

The length of time you can rent a vacation rental in Kailua is down to the property. Simply enter your preferred dates to view a list of options offering extended stays. With a range of features like full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to discover somewhere perfect to call your home away from home in Kailua.

More Vacation Rentals ideas

People also search for