Kailua Holiday Rentals

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Holiday Rentals in Kailua

Maui Beach Vacation Club
2.5 star property
8.2 out of 10, Very good, (802)
"Room was quiet, no ac but the breeze came through very nice. Comfortable and convenient location. "
Maui Beach Vacation Club
Yonegan Maui Getaways - Haiku
3.0 star property
9.0 out of 10, Wonderful, (7)
"Loved having the hot tub to come home to!!"
The price is AU$356
includes taxes & fees
27 Oct - 28 Oct
Yonegan Maui Getaways - Haiku
Maui Sunset
3.5 star property
8.8 out of 10, Excellent, (474)
"Good place to spend your vacation "
Maui Sunset
Oceanview Condo in Hana-Let the ocean lull you to sleep
9.2 out of 10, Wonderful, (107)
"A good place to stay "
The price is AU$619
includes taxes & fees
22 Oct - 23 Oct
Oceanview Condo in Hana-Let the ocean lull you to sleep
Maui Schooner Resort
3.5 star property
9.2 out of 10, Wonderful, (492)
"Nice amenities and huge space. Nice pool and spa."
Maui Schooner Resort
Sugar Beach Resort
3.0 star property
8.6 out of 10, Excellent, (1093)
"We loved it there! "
Sugar Beach Resort
Wonderful South Maui Beach Condos
3.5 star property
9.4 out of 10, Exceptional, (23)
"Exactly what we needed with beach access right across the street"
Wonderful South Maui Beach Condos
Kaiholo Hale
3.0 star property
9.4 out of 10, Exceptional, (201)
"Area was quiet but close to amenities. We could drive anywhere on Maui easily. There was a lovely beach less than a block from the suite with good snorkeling and friendly locals. Bed in the suite was very comfortable, and it had everything we needed for a relaxing vacation."
Kaiholo Hale
Sugar Beach Resort - Maui Condo & Home
3.0 star property
8.4 out of 10, Very good, (514)
"Love this location, great beach, quiet."
Sugar Beach Resort - Maui Condo & Home
Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting
10.0 out of 10, Exceptional, (267)
"Our family had a great time at the condo in Kihei. The rooms were spacious, the place had everything you need for cooking and the beach (minus life jackets but those were easy to rent). The location was perfect and within walking distance of tons of restaurants, shops, and the ocean. I would definitely recommend this place and if we're ever in the area again would happily stay there."
Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting
Sleeps 4, Full kitchen & AC. Pool, hot tub, tennis court, bbq grills! And Beach!
9.8 out of 10, Exceptional, (73)
"We enjoyed our stay. Pool was easily accessible and quiet everyday. Great location "
Sleeps 4, Full kitchen & AC. Pool, hot tub, tennis court, bbq grills! And Beach!
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
9.4 out of 10, Exceptional, (53)
"Awesome stay!!"
The price is AU$557
includes taxes & fees
3 Nov - 4 Nov
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Kihei Bay Surf 227
3.5 star property
9.4 out of 10, Exceptional, (17)
"The neighbors were friendly, the room was great, location was perfect, no complaints here"
Kihei Bay Surf 227
Best Oceanfront Value in Kihei - Kealia Resort!
9.6 out of 10, Exceptional, (107)
"The condo was exactly as described and in a great location, we loved the grassy area right in front of the beach if we didn’t feel like sitting in the sand! Tim had all the essentials for us and was quick to respond if we had any questions- we would definitely stay here again in the future! "
The price is AU$686
includes taxes & fees
27 Oct - 28 Oct
Best Oceanfront Value in Kihei - Kealia Resort!
Koa Resort 2 Bed Ground Floor Condo -Air Conditioning
9.4 out of 10, Exceptional, (175)
"Like everything Except a few island bugs "
Koa Resort 2 Bed Ground Floor Condo -Air Conditioning
Maui Vista – Maui Condo & Home
4.0 star property
8.4 out of 10, Very good, (53)
"Great for working trip. "
Maui Vista – Maui Condo & Home
Great Rates - Clean and Cozy Condo!
9.8 out of 10, Exceptional, (159)
"Excellent communication with owner. Property was easily accessible with clear instructions to access the key. I liked that it was on the ground floor. Good central location with shipping, restaurants and various activities nearby. "
Great Rates - Clean and Cozy Condo!
Sweeping Unobstructed Ocean Views, Luxury Beachfront Condo, Wonderful Lanai
9.6 out of 10, Exceptional, (92)
"We had a wonderful stay for our first time in Hawaii. This property is fairly well equipped and in an wonderfully central location. "
Sweeping Unobstructed Ocean Views, Luxury Beachfront Condo, Wonderful Lanai
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
10.0 out of 10, Exceptional, (180)
"Luxury without all the people around"
The price is AU$1,664
includes taxes & fees
15 Oct - 16 Oct
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
9.8 out of 10, Exceptional, (258)
"Very clean, close to beaches and town. The host was also great with communication and recommendations. Highly recommend! "
The price is AU$606
includes taxes & fees
11 Nov - 12 Nov
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Kailua Hotel Reviews

Find out more about Kailua

Everything you need to know about Kailua holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kailua holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kailua holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Kailua holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kailua. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kailua holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kailua holiday rentals we have selected for you start as low as AU$356 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Kailua rentals

At Expedia, we put the best Kailua holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Kailua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kailua holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kailua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Kailua?

Yes, there are holiday rentals close to the most popular sights in Kailua, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Kailua has to offer?

Yonegan Maui Getaways - Haiku : This holiday home rental outside of Kailua is located near the beach, and has 1 hot tub, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a microwave, a coffee maker and kitchenware.

What’s there to see and do in Kailua?

While exploring the area, visit family-friendly sights like Waikamoi Preserve, or get outside and enjoy nature at Twin Falls. In the wider area, you’ll find Garden of Eden Arboretum and Maui Garden Of Eden - Botanical Gardens & Arboretum.

What’s a holiday rental in Kailua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kailua. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a small group gathering.