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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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Kailua holiday rentals

In-room dining

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.4 out of 10, Exceptional, (39 reviews)
"We had a wonderful stay at this condo. It was clean, spacious, and well equipped with everything we needed. The kitchen was very convenient, and the location was great. We especially appreciated how comfortable and well maintained the condo was. We would definitely stay here again."
United States
Nataliia
The price is S$671
includes taxes & fees
16 Jun - 17 Jun
Kihei Ali'i Kai Condos with Free Parking
Terrace/patio

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (31 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is S$408
includes taxes & fees
22 Jun - 23 Jun
Yonegan Maui Getaways - Haiku
Interior

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 S$493
includes taxes & fees
22 Jun - 23 Jun
Lanai & Steps to Beach! Stunning South Maui Condo
Dining room

The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is S$831
includes taxes & fees
19 Jun - 20 Jun
The Ocean View Residence
Interior

Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is S$1,079
includes taxes & fees
16 Jun - 17 Jun
Kuau Plaza Paia Condo with Parking
On the beach, white sand, beach towels

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)
"Grounds were beautiful. Beach view and access great. Quality of condo was in need of refreshing. Some broken doors, and in need of repair. The condo was clean."
United States
Eric
The price is S$704
includes taxes & fees
18 Jun - 19 Jun
Waiohuli Beach Hale Ocean View Condos with Parking
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

Howzit Hostels

Howzit Hostels

10/10 Excellent
"everyone was helpful & the place was very clean & inviting"
ABEL 12-night trip
Posted 8 hours ago
Howzit Hostels

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 Maui Spa Retreat.

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.