Kailua Holiday Rentals

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Holiday Rentals in Kailua

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (792)
"Just a great stay! "
Maui Beach Vacation Club

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (466)
"Located on the beach with beautiful sunsets and large pool and hot tub."
Maui Sunset

Yonegan Maui Getaways - Haiku

3.0 star property
9.0 out of 10, Wonderful, (4)
"It was a last minute stay and it had what we needed. "
The price is AU$397
includes taxes & fees
31 Aug - 1 Sept
Yonegan Maui Getaways - Haiku

Maui Schooner Resort

3.5 star property
9.2 out of 10, Wonderful, (486)
"Room setup is very convenient for a group of 6 with 2 full baths. Landscape looks nice."
Maui Schooner Resort

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1087)
"Good location, easy access to beach"
Sugar Beach Resort

Oceanview Condo in Hana-Let the ocean lull you to sleep

9.2 out of 10, Wonderful, (105)
"An idyllic setting where we could see the bay, hear the waves, with a short walk to the beach (black rocky sands). Neighbors a bit loud, but still one of the best spots in Hāna. Easy drive to the 7 sacred pools. Good food trucks nearby. "
The price is AU$679
includes taxes & fees
9 Sept - 10 Sept
Oceanview Condo in Hana-Let the ocean lull you to sleep

Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting

10.0 out of 10, Exceptional, (261)
"Completely remodeled and location is excellent! Host were great!"
Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

10.0 out of 10, Exceptional, (67)
"16 of us stayed at this beautiful property. Two Families, 12 children total. We have nothing bad to say. All of our expectations were met. The listing is true and accurate. Communication with the property manager was always prompt and efficient.We would definitely stay her again."
The price is AU$4,360
includes taxes & fees
10 Sept - 11 Sept
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

BEACHFRONT MAUI KIHEI HOUSE

9.8 out of 10, Exceptional, (166)
"Celebrating my husband’s retirement with our grown children and significant others. This was a perfect place for us. The house is beautiful, the yard, the beach, the location. All 9 adults were very happy to be here!"
BEACHFRONT MAUI KIHEI HOUSE

Maui Sunset B123 Beachfront, Ocean View, Ground Floor Families! Pool! 3 Bedrooms

9.8 out of 10, Exceptional, (55)
"We’ve been going there since about 1985. Love the location and the grounds. We like a ground unit so we can just flow to the outside "
Maui Sunset B123 Beachfront, Ocean View, Ground Floor Families! Pool! 3 Bedrooms

OCEAN FRONT: spacious, remodeled 4th floor condo

9.4 out of 10, Exceptional, (72)
"The corner ocean view 3 bedroom condo was perfect for my family. The condo was accessible with the elevator for my mom as well."
OCEAN FRONT: spacious, remodeled 4th floor condo

Sugar Beach Resort - Maui Condo & Home

3.0 star property
8.4 out of 10, Very good, (514)
"Love this location, great beach, quiet."
Sugar Beach Resort - Maui Condo & Home

Maui Sunset B120 Beachfront, Ground Floor, Ocean-View, Families! Amenities! Pool

10.0 out of 10, Exceptional, (71)
"Great condo. Great location. Could not have asked for a better place to stay with my family (two kids under 5). The grounds are well kept and staff are friendly. "
Maui Sunset B120 Beachfront, Ground Floor, Ocean-View, Families! Amenities! Pool

Awesome Maui Vista Beach Suite

4.0 star property
9.0 out of 10, Wonderful, (17)
"Accommodations were great..would stay again! "
The price is AU$780
includes taxes & fees
30 Aug - 31 Aug
Awesome Maui Vista Beach Suite

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

10.0 out of 10, Exceptional, (228)
"Lovely property and very enjoyable place to stay. Great location."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (199)
"We stayed here 4 nights, perfect location for our activities. We did sunrise bike ride down Haleakala and Road to Hana. "
Kaiholo Hale

Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

9.8 out of 10, Exceptional, (203)
"We enjoyed our time at this beautiful piece of property. The yard was amazing and the lanai was definitely the hang out spot. "
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

Chic & Elegant Oceanfront Vistas

4.0 star property
9.8 out of 10, Exceptional, (25)
"Pretty standard condos. Nice beaches and restaurants nearby. "
Chic & Elegant Oceanfront Vistas

MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning

9.6 out of 10, Exceptional, (200)
"Very comfortable and perfect location for food, surf and fun! Condo was great and had what we needed to enjoy our stay. Thank you!!"
MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning

Spectacular Ocean Maui Sunset View

9.8 out of 10, Exceptional, (124)
"We truly enjoyed the location, watching the turtles come ashore at night and the easy walk to the beach! "
Spectacular Ocean Maui Sunset View
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

Find out more about Kailua

Find out more about Kailua

Everything you need to know about Kailua holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kailua holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kailua holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Kailua holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kailua. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kailua holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kailua holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Kailua rentals

At Expedia, we put the best Kailua holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Kailua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kailua holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kailua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Twin Falls. 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.