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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Kailua holiday rentals

A wooden deck with a chair, surrounded by lush tropical vegetation and a clear blue sky.

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 HK$992
HK$2,354 total
includes taxes & fees
4 Oct - 5 Oct
Yonegan Maui Getaways - Haiku
A coastal resort with beachfront properties, palm trees, and a view of distant mountains.

2. Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is HK$4,040
HK$7,580 total
includes taxes & fees
30 Sept - 1 Oct
Kuau Plaza Paia Condo with Parking
A beach with clear blue water, rocky shore, and palm trees.

3. 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 HK$1,326
HK$3,282 total
includes taxes & fees
5 Oct - 6 Oct
Condo w/ Lanai at Beginning of Road to Hana!
A resort with a pool area, palm trees, and a view of the ocean.

4. 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 HK$1,319
HK$7,848 total
includes taxes & fees
30 Sept - 1 Oct
Kauhale Makai by Coldwell Banker Island Vacations
A beach with clear blue water, a sandy shore, and palm trees.

5. 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 HK$2,247
HK$8,061 total
includes taxes & fees
4 Oct - 5 Oct
The Kalama Residence
A modern living room with a sofa, coffee table, and a view of the ocean.

6. 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 HK$4,738
HK$8,129 total
includes taxes & fees
30 Sept - 1 Oct
2BR/2BA Oceanfront Condo in Maui Sunset
A tropical beach scene with palm trees, a clear blue sky, and a view of the ocean.

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 HK$1,443
HK$4,125 total
includes taxes & fees
1 Oct - 2 Oct
Waiohuli Beach Hale Ocean View Condos with Parking
A modern kitchen with a large island, a dining area with a view, and a living room with a sofa and chairs.

8. 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 HK$1,443
HK$4,125 total
includes taxes & fees
30 Sept - 1 Oct
Kihei Ali'i Kai Condos with Free Parking
A beach with a building on the left, a rocky breakwater, and a clear blue sky.

9. 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 HK$1,851
HK$3,906 total
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

Gods Peace Of Maui

Gods Peace Of Maui

10/10 Excellent
"Simple and easy to stay. Parking in 5 seconds away, clean room and shower and toilet. Clean towels and blanket - thoughtfully placed. Kettle and microwave in the kitchen. Best beautiful and affordable place to stay."
akiko 4-night trip
Posted 1 hour ago
Gods Peace Of Maui

Find out more about Kailua

Search for holiday rentals in Kailua on Expedia! You can easily find your home rentals, villas, holiday apartments in Kailua using one of the methods below:

  • View our selection of featured holiday rentals in Kailua
  • Use the map to find apartments and other holiday homes in the Kailua neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Kailua while they last

Look no further and take a look at our great range of rental properties in Kailua!

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.