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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Kailua holiday rentals

Terrace/patio

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (36 reviews)
"Large room and bathroom. Nice little kitchen area. We had a room with two balconies so great air flow through to cool the room. Beautiful area of Hawaii to explore"
Canada
Amanda
The price is S$409
includes taxes & fees
5 Aug - 6 Aug
Yonegan Maui Getaways - Haiku
Interior

2. Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is S$1,443
includes taxes & fees
7 Aug - 8 Aug
Kuau Plaza Paia Condo with Parking
Property grounds

3. Kauhale Makai by Coldwell Banker Island Vacations

Kauhale Makai by Coldwell Banker Island Vacations
3.0 star property
Central Kihei
8.0 out of 10, Very good, (1 review)
"Stayed in Kauhale Makai 102 for 7 nights. A few suggestions: -since it is a studio, consider upgrading the refrigerator to a quieter model that does't sound like a noisy engine running right next to you ! - the mattress needs replacing, very saggy in the middle and way too soft"
United States
petru
The price is S$1,235
includes taxes & fees
2 Aug - 3 Aug
Kauhale Makai by Coldwell Banker Island Vacations
On the beach, white sand

4. 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 S$1,079
includes taxes & fees
31 Jul - 1 Aug
The Kalama Residence
Interior

5. 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$504
includes taxes & fees
6 Aug - 7 Aug
Lanai & Steps to Beach! Stunning South Maui Condo
Dining room

6. The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (2 reviews)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is S$722
includes taxes & fees
3 Aug - 4 Aug
The Ocean View Residence
On the beach, white sand, beach towels

7. 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 S$748
includes taxes & fees
31 Jul - 1 Aug
Waiohuli Beach Hale Ocean View Condos with Parking
Living area

8. 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 S$1,417
includes taxes & fees
6 Aug - 7 Aug
2BR/2BA Oceanfront Condo in Maui Sunset
Living area

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, (49 reviews)
"The place was super nice and seemed pretty modern. There was a big tv mounted on the wall and the living room was nice to relax in, the kitchen and bathroom were clean too. There was a little patio as well and they had beach chairs/umbrellas you could take. They had a pool, hot tub, and sauna which were all really great too!"
United States
Jagdish
The price is S$736
includes taxes & fees
26 Aug - 27 Aug
Kihei Ali'i Kai Condos with Free Parking
Front of property

10. Ocean-view Kihei Condo w/ Lanai: Steps to Beach!

Ocean-view Kihei Condo w/ Lanai: Steps to Beach!
3.0 star property
North Kihei
The price is S$998
includes taxes & fees
12 Aug - 13 Aug
Ocean-view Kihei Condo w/ Lanai: Steps to Beach!
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

Maui Sunset

Maui Sunset

10/10 Excellent
"A better value and more comfortable than the more expensive Kaanapali and Kahana resorts. Check in was a breeze. The unit was clean and well stocked, notably with great cookware and utensils to accommodate baking, grilling, and stovetop cooking. The property was well manicured, spotless, with direct beach access. The evening live music mid week was a gem of local artistry. Sunset beach meetups bring locals and guests together for spectacular sunsets. Gym was well equipped for cardio and weights, with a sauna."
Stefanie 10-night trip
Posted 13 hours ago
Maui Sunset

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 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.