Kailua Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Kailua

Aparthotel in North Kihei

2.5 star property
8.2 out of 10, Very good, (817)
"A excelent service in the office. Nice and clean room y all the hotel. I recommend this hotel."
United States
Blanca I
Maui Beach Vacation Club

Holiday Home in Haiku

3.0 star property
9.2 out of 10, Wonderful, (9)
"Loved having the hot tub to come home to!!"
United States
Pedro
The price is AU$399
includes taxes & fees
1 Dec - 2 Dec
Yonegan Maui Getaways - Haiku

Aparthotel in Central Kihei

3.5 star property
8.8 out of 10, Excellent, (478)
"Good place to spend your vacation "
United States
Tomasz
Maui Sunset

Aparthotel in Central Kihei

3.5 star property
9.2 out of 10, Wonderful, (496)
"Nice amenities and huge space. Nice pool and spa."
United States
Danyang
Maui Schooner Resort

Aparthotel in North Kihei

3.0 star property
8.6 out of 10, Excellent, (1099)
"We loved it there! "
United States
Babatunde
Sugar Beach Resort

Condo in South Kihei

3.5 star property
9.4 out of 10, Exceptional, (28)
"Direct beach access walkable access to everything you could need "
United States
Scott
Wonderful South Maui Beach Condos

Condo in South Kihei

9.4 out of 10, Exceptional, (89)
"AC could have been more effective but worked OK when we ran the fans. Good view of the mountains from the balcony..."
United States
Jeffrey
Time Beach @ Grand Van Kleef

Apartment in South Kihei

4.0 star property
9.0 out of 10, Wonderful, (20)
"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
Kihei Ali'i Kai Condos with Free Parking

Villa in South Kihei

10.0 out of 10, Exceptional, (68)
"This was an amazing place in a great location. Slept 6 adults very comfortably. Would definitely recommend this place to others. "
United States
Denis B.
Gated 2-story beach house with big yard

Holiday Home in North Kihei

9.8 out of 10, Exceptional, (207)
"Perfect home for a large group. Beach is across the street the back to the pool when the waves got to be to much for our little ones. Great property manager! Great location! "
United States
sandy C.
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

Condo in South Kihei

9.8 out of 10, Exceptional, (192)
"Had a wonderful experience staying here! A sweet, cozy and comfortable little getaway for our family and little one!"
United States
Misty
The price is AU$701
includes taxes & fees
29 Nov - 30 Nov
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores

Apartment in Central Kihei

3.0 star property
10.0 out of 10, Exceptional, (3)
"We had a wonderful stay in this condo. It had everything we needed for a fun Hawaiian beach vacation. They stocked it with beach chairs, a cooler, and even a boogie board. The kitchen had everything we needed, although we didn't cook that much. Management was super responsive whenever we had any issues. It was just enough space for our family of four. The beach was just steps away and the pool was also very nice. "
United States
Anthony
The price is AU$776
includes taxes & fees
11 Dec - 12 Dec
Waiohuli Beach Hale Ocean View Condos with Parking

Holiday Home in Makawao

10.0 out of 10, Exceptional, (231)
"I absolutely love staying here! It’s a new yearly tradition and great location! "
United States
Courtney P.
Private lush 2 Acre Mountain Home Maui w/ many amenities

Holiday Home in Paia

3.0 star property
9.4 out of 10, Exceptional, (201)
"Area was quiet but close to amenities. We could drive anywhere on Maui easily. There was a lovely beach less than a block from the suite with good snorkeling and friendly locals. Bed in the suite was very comfortable, and it had everything we needed for a relaxing vacation."
United States
Carley
Kaiholo Hale

Holiday Home in Central Kihei

9.8 out of 10, Exceptional, (58)
"Mark was wonderful to work with. Some things could use some updates but overall it was a great location and we had a great stay."
United States
Tiffany S.
Kihei Maui Beach house - On the water

Aparthotel in North Kihei

3.0 star property
8.4 out of 10, Very good, (516)
"Love this location, great beach, quiet."
United States
Nataliya
Sugar Beach Resort - Maui Condo & Home

Condo in South Kihei

2.5 star property
10.0 out of 10, Exceptional, (6)
"Such a great location. Close to several walkable restaurants, shops and beautiful beaches! We felt at home!"
United States
Lorna R.
Tropical Oasis! Beaches, Shopping and Comfort Pacific Shores A212

Holiday Home in Central Kihei

10.0 out of 10, Exceptional, (152)
"Could not have been better!! This was our third time renting this house, and Michael has always been the perfect host. We are definitely going back, God willing!"
United States
John C.
Quiet Beachfront Large Family Estate... Great for multiple families . Sleeps 12

Condo in South Kihei

4.0 star property
8.4 out of 10, Very good, (53)
"Great for working trip. "
United States
Andrew
Maui Vista – Maui Condo & Home

Condo in South Kihei

9.4 out of 10, Exceptional, (163)
"Terrific location in a spotlessly clean condo with everything you could ask for. Right next to the amazing Food Park Oasis. Would happily stay here again. "
United States
John W.
2B2B Oceanfront Condo, Oceanview in masterbed and living RM ^summer 2025 on sale
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.

Black Friday Sale

Save up to 40% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

Top Kailua Hotel Reviews

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 AU$399 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.