Kailua Vacation Rentals

  • 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
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Kailua vacation 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, (30 reviews)
"The location was great, especially if you plan to see the whole island! Easy check in and check out. Clean place."
United States
Weronika
The price is NT$5,138
NT$10,826 total
includes taxes & fees
Apr 27 - Apr 28
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 NT$8,509
NT$18,893 total
includes taxes & fees
Apr 26 - Apr 27
Kuau Plaza Paia Condo with Parking
Apartment (1 Bedroom) | Interior

Stunning South Maui Condo w/ Lanai by Beach!

Stunning South Maui Condo w/ Lanai by Beach!
3.5 star property
North Kihei
The price is NT$3,687
NT$12,109 total
includes taxes & fees
May 6 - May 7
Stunning South Maui Condo w/ Lanai by Beach!
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
The price is NT$4,916
NT$14,592 total
includes taxes & fees
Apr 26 - Apr 27
Waiohuli Beach Hale Ocean View Condos with Parking
Family Apartment, 2 Bedrooms, Balcony, Mountain View (1012) | 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
9.2 out of 10, Wonderful, (32 reviews)
"Everything was set up to be an amazing experience and we would definitely stay again."
Canada
Tamara
The price is NT$4,254
NT$13,263 total
includes taxes & fees
Apr 27 - Apr 28
Kihei Ali'i Kai Condos with Free Parking
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
8.0 out of 10, Very Good, (1 review)
The price is NT$8,509
NT$19,050 total
includes taxes & fees
Apr 27 - Apr 28
2BR/2BA Oceanfront Condo in Maui Sunset
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
"Very friendly staff. Its a smaller hotel, not like a big resort so the atmosphere felt more relaxed. The restaurant at the hotel had very delicious food. "
Yvette 1-night trip
Posted 14 hours 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 vacation rental in Kailua?

Yes, there are vacation rentals near top sights in Kailua, or you can select a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals that Kailua has to offer?

Yonegan Maui Getaways - Haiku : This vacation home rental near Kailua is located near the beach and has a hot tub, a barbecue grill, 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 larger area, you’ll find Twin Falls and Maui Garden Of Eden - Botanical Gardens & Arboretum.

What’s a vacation rental in Kailua like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Kailua. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.