An aerial view of a coastal town with clear turquoise waters, two prominent islands, and lush green hills.

Kailua Holiday Rentals

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Our top choices for Kailua holiday rentals

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (37 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is NZ$536
includes taxes & fees
14 Oct - 15 Oct
Yonegan Maui Getaways - Haiku

2. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
3.0 star property
Haiku
The price is NZ$2,223
includes taxes & fees
31 Oct - 1 Nov
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

3. Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is NZ$1,718
includes taxes & fees
17 Oct - 18 Oct
Kuau Plaza Paia Condo with Parking

4. Wonderful South Maui Beach Condos

Wonderful South Maui Beach Condos
3.5 star property
South Kihei
9.2 out of 10, Wonderful, (44 reviews)
"Great location, perfect for my trip. "
United States
John
The price is NZ$876
includes taxes & fees
1 Nov - 2 Nov
Wonderful South Maui Beach Condos

5. The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
9.4 out of 10, Exceptional, (3 reviews)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is NZ$1,196
includes taxes & fees
9 Oct - 10 Oct
The Ocean View Residence

6. The Kalama Residence

The Kalama Residence
3.0 star property
South Kihei
8.0 out of 10, Very good, (3 reviews)
"My stay was okay. "
United States
Rosalba
The price is NZ$1,647
includes taxes & fees
14 Oct - 15 Oct
The Kalama Residence

7. Awesome Maui Vista Beach Suite

Awesome Maui Vista Beach Suite
4.0 star property
South Kihei
8.6 out of 10, Excellent, (27 reviews)
"Absolutely perfect!!! Flavor of Hawaii!!"
United States
Laura
The price is NZ$891
includes taxes & fees
1 Nov - 2 Nov
Awesome Maui Vista Beach Suite

8. Condo w/ Lanai at Beginning of Road to Hana!

Condo w/ Lanai at Beginning of Road to Hana!
3.0 star property
Paia
The price is NZ$747
includes taxes & fees
9 Oct - 10 Oct
Condo w/ Lanai at Beginning of Road to Hana!

9. Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.6 out of 10, Exceptional, (54 reviews)
"Absolutely an amazing place. Very nice, clean, comfortable. We stayed in B104 and it is a perfect spot to get in and out. Definitely come back again."
United States
Angeline
The price is NZ$887
includes taxes & fees
10 Oct - 11 Oct
Kihei Ali'i Kai Condos with Free Parking

10. Waiohuli Beach Hale Ocean View Condos with Parking

Waiohuli Beach Hale Ocean View Condos with Parking
3.0 star property
Central Kihei
9.8 out of 10, Exceptional, (6 reviews)
"Easy access to the beach, nice kitchen, view of the water"
United States
Phillip J
The price is NZ$975
includes taxes & fees
22 Oct - 23 Oct
Waiohuli Beach Hale Ocean View Condos with Parking

11. 2BR/2BA Oceanfront Condo in Maui Sunset

2BR/2BA Oceanfront Condo in Maui Sunset
3.5 star property
Central Kihei
8.0 out of 10, Very good, (1 review)
The price is NZ$1,851
includes taxes & fees
9 Oct - 10 Oct
2BR/2BA Oceanfront Condo in Maui Sunset

12. Lanai & Steps to Beach! Stunning South Maui Condo

Lanai & Steps to Beach! Stunning South Maui Condo
3.5 star property
North Kihei
The price is NZ$889
includes taxes & fees
15 Oct - 16 Oct
Lanai & Steps to Beach! Stunning South Maui Condo
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kailua holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Kailua. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Kailua. Seeing all the best attractions is bound to make you fall in love with Kailua. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Kailua short-term rentals, that won’t be hard to do.

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 Haleakala National Park. In the wider area, you’ll find Maui Garden Of Eden - Botanical Gardens & Arboretum and Makawao Park.

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.