Kailua Holiday Rentals

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Kailua holiday rentals

Terrace/patio

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.6 out of 10, Excellent, (20 reviews)
"It is a cozy place. It has all the amenities. It feels like home"
United States
Roberto
The price is S$353
includes taxes & fees
24 Feb - 25 Feb
Yonegan Maui Getaways - Haiku
Interior

Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is S$766
includes taxes & fees
30 Jan - 31 Jan
Kuau Plaza Paia Condo with Parking
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 Ocean View Residence
On the beach, white sand

The Kalama Residence

The Kalama Residence
3.0 star property
South Kihei
7.0 out of 10, Good, (2 reviews)
"My stay was okay. "
United States
Rosalba
The price is S$1,712
includes taxes & fees
12 Feb - 13 Feb
The Kalama Residence
Interior

Menehune Shores 223 2 Bedroom Condo

Menehune Shores 223 2 Bedroom Condo
3.0 star property
Kihei
Menehune Shores 223 2 Bedroom Condo
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
9.0 out of 10, Wonderful, (21 reviews)
"I loved that it was a short walk to the beach and there were grocery stores nearby. Lots of options of places to eat and shop and explore the island!"
United States
Emma
The price is S$547
includes taxes & fees
31 Jan - 1 Feb
Kihei Ali'i Kai Condos with Free 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
10.0 out of 10, Exceptional, (5 reviews)
"Easy access to the beach, nice kitchen, view of the water"
United States
Phillip J
Waiohuli Beach Hale Ocean View Condos with Parking
Pool

Luana Kai C210 2 Bedroom Condo

Luana Kai C210 2 Bedroom Condo
3.0 star property
Kihei
Luana Kai C210 2 Bedroom Condo
Living area

2BR/2BA Oceanfront Condo in Maui Sunset

2BR/2BA Oceanfront Condo in Maui Sunset
3.5 star property
Central Kihei
The price is S$786
includes taxes & fees
29 Jan - 30 Jan
2BR/2BA Oceanfront Condo in Maui Sunset
Beach

Maui Vista 3307 1 Bedroom Condo

Maui Vista 3307 1 Bedroom Condo
3.0 star property
Kihei
Maui Vista 3307 1 Bedroom Condo
Interior

Menehune Shores 227 2 Bedroom Condo

Menehune Shores 227 2 Bedroom Condo
3.5 star property
Kihei
Menehune Shores 227 2 Bedroom Condo
Property grounds

Menehune Shores 601 2 Bedroom Condo

Menehune Shores 601 2 Bedroom Condo
3.0 star property
Kihei
Menehune Shores 601 2 Bedroom Condo
Terrace/patio

Maui Vista 1315 1 Bedroom Condo

Maui Vista 1315 1 Bedroom Condo
3.0 star property
Kihei
Maui Vista 1315 1 Bedroom Condo
Living area

Maui Vista 3213 1 Bedroom Condo

Maui Vista 3213 1 Bedroom Condo
3.0 star property
Kihei
Maui Vista 3213 1 Bedroom 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

Howzit Hostels

Howzit Hostels

10/10 Excellent
"I really love all their service,atleast at all times the stuff is their to help,May God Richly bless all of you see you again nex time😍✅"
Bernice 5-night trip
Posted 2 days 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 Garden of Eden Arboretum. 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.