Kailua vacation rentals

We found 89 vacation rentals — enter your dates for availability

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.
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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)
  • Enlighten Up Massage (7.4 mi / 11.9 km)
  • Waikamoi Preserve (12.8 mi / 20.7 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)
  • Garden of Eden Arboretum (3 mi / 4.8 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)

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?
Length of stay, season and property type are some things that can determine the price of a vacation home. Simply enter your dates of travel to find your perfect match. From comfy cabins to sprawling villas, all Vrbo vacation rentals provide amazing value.
How much does it cost to rent a beach house in Kailua?
Prices for beach houses in Kailua can differ depending on the size and style of the property and when you’re traveling. Simply enter your travel dates into Vrbo and how many guests to view vacation rental options and prices. From there you can use our filter tool to narrow your search by ratings, nearby activities, amenities and more.
How old do you have to be to rent a vacation rental in Kailua?
The minimum age requirements can differ between properties on Vrbo, so look at the rules of the vacation rental in Kailua you’re interested in. But typically, it’s 16, 18 or 21.
How long can I rent a vacation rental in Kailua for?
It really depends on the Kailua property. To view a list of options offering extended stays, just enter your dates and number of people into Vrbo. Look forward to having the whole place to yourself, as well as comforts such as air conditioning, a kitchen and an outdoor space to play in. Keep your eyes open for long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Kailua?
In Kailua, you’ll find some incredible bargains and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re after a mini escape or a couple of weeks away, we have a host of options that’ll suit your style.

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