Search Holiday Rentals in Kailua

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Kailua holiday rentals

Studio, Garden View (Haiku #6) | Terrace/patio

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (25 reviews)
"It is a cozy place. It has all the amenities. It feels like home"
United States
Roberto
The price is ฿5,220
฿9,273 total
includes taxes & fees
10 Mar - 11 Mar
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 ฿7,772
฿17,900 total
includes taxes & fees
8 Mar - 9 Mar
Kuau Plaza Paia Condo with Parking
Condo, 2 Bedrooms | Interior

Menehune Shores 227 2 Bedroom Condo

Menehune Shores 227 2 Bedroom Condo
3.5 star property
North Kihei
The price is ฿9,970
฿34,008 total
includes taxes & fees
1 Mar - 2 Mar
Menehune Shores 227 2 Bedroom Condo
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 ฿7,177
฿28,254 total
includes taxes & fees
5 Mar - 6 Mar
The Kalama Residence
Elite Apartment, Balcony, Ocean View | 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 ฿5,523
฿24,718 total
includes taxes & fees
13 Mar - 14 Mar
The Ocean View Residence
Family Apartment, 2 Bedrooms, 2 Bathrooms, Ocean View (1015) | Living area | 50-inch TV with digital channels

2BR/2BA Oceanfront Condo in Maui Sunset

2BR/2BA Oceanfront Condo in Maui Sunset
3.5 star property
Central Kihei
The price is ฿10,943
฿21,820 total
includes taxes & fees
1 Mar - 2 Mar
2BR/2BA Oceanfront Condo in Maui Sunset
Condo, 2 Bedrooms | Pool

Luana Kai C210 2 Bedroom Condo

Luana Kai C210 2 Bedroom Condo
3.0 star property
Central Kihei
The price is ฿9,518
฿33,199 total
includes taxes & fees
11 Mar - 12 Mar
Luana Kai C210 2 Bedroom Condo
Condo, 2 Bedrooms | Pool

Luana Kai A104 2 Bedroom Condo

Luana Kai A104 2 Bedroom Condo
3.0 star property
Central Kihei
The price is ฿9,669
฿33,468 total
includes taxes & fees
30 Mar - 31 Mar
Luana Kai A104 2 Bedroom Condo
Condo, 1 Bedroom | Terrace/patio

Maui Vista 1315 1 Bedroom Condo

Maui Vista 1315 1 Bedroom Condo
3.0 star property
South Kihei
The price is ฿7,374
฿23,266 total
includes taxes & fees
10 Mar - 11 Mar
Maui Vista 1315 1 Bedroom Condo
Condo, 1 Bedroom | Beach

Maui Vista 3307 1 Bedroom Condo

Maui Vista 3307 1 Bedroom Condo
3.0 star property
South Kihei
The price is ฿6,882
฿22,378 total
includes taxes & fees
12 Mar - 13 Mar
Maui Vista 3307 1 Bedroom Condo
Condo, 2 Bedrooms | Property grounds

Menehune Shores 601 2 Bedroom Condo

Menehune Shores 601 2 Bedroom Condo
3.0 star property
North Kihei
The price is ฿11,663
฿37,043 total
includes taxes & fees
4 Mar - 5 Mar
Menehune Shores 601 2 Bedroom Condo
Condo, 2 Bedrooms | Interior

Menehune Shores 223 2 Bedroom Condo

Menehune Shores 223 2 Bedroom Condo
3.0 star property
North Kihei
The price is ฿11,845
฿37,362 total
includes taxes & fees
9 Mar - 10 Mar
Menehune Shores 223 2 Bedroom Condo
Family Apartment, 2 Bedrooms, Balcony, Mountain View | 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
8.8 out of 10, Excellent, (26 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 ฿5,397
฿14,697 total
includes taxes & fees
29 Mar - 30 Mar
Kihei Ali'i Kai Condos with Free Parking
Condo, 1 Bedroom | Living area | Smart TV

Maui Vista 3213 1 Bedroom Condo

Maui Vista 3213 1 Bedroom Condo
3.0 star property
South Kihei
The price is ฿7,449
฿23,401 total
includes taxes & fees
25 Mar - 26 Mar
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kailua Hotel Reviews

Maui Seaside Hotel

Maui Seaside Hotel

10/10 Excellent
"We liked it. Seems a typical dated motel room, ours had parking lot view, "should" cost less. But quitet, we could hear ocean (it's beachfront,) next to park and amazing coffee shop, and great restaurant attached. "
PATRICK 1-night trip
Posted 1 day ago
Maui Seaside Hotel

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 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.