Kailua Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Kailua vacation rentals

A wooden deck with a chair, surrounded by lush tropical vegetation and a clear blue sky.

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (42 reviews)
"The place was just as described. The host was great. Definitely recommend."
United States
Nancy
The price is CA $197
CA $444 total
includes taxes & fees
Nov 8 - Nov 9
Yonegan Maui Getaways - Haiku
A spacious kitchen with a large island, wooden flooring, and modern lighting fixtures.

2. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
3.0 star property
Haiku
The price is CA $803
CA $1,745 total
includes taxes & fees
Nov 30 - Dec 1
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
A coastal resort with beachfront properties, palm trees, and a view of distant mountains.

3. Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is CA $720
CA $1,350 total
includes taxes & fees
Nov 16 - Nov 17
Kuau Plaza Paia Condo with Parking
A dining area with a table set for breakfast, including bread, fruit, and orange juice.

4. The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
9.4 out of 10, Exceptional, (3 reviews)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is CA $161
CA $924 total
includes taxes & fees
Nov 11 - Nov 12
The Ocean View Residence
A beach with clear blue water, a sandy shore, and palm trees.

5. The Kalama Residence

The Kalama Residence
3.0 star property
South Kihei
8.0 out of 10, Very good, (3 reviews)
"My stay was okay. "
United States
Rosalba
The price is CA $241
CA $1,097 total
includes taxes & fees
Nov 13 - Nov 14
The Kalama Residence
A beach with clear turquoise water, a sandy shore, and a distant mountain.

6. Wonderful South Maui Beach Condos

Wonderful South Maui Beach Condos
3.5 star property
South Kihei
9.2 out of 10, Wonderful, (46 reviews)
"The place was great, had everything we needed and communication with the host was fantastic. Highly recommended!"
Canada
Dan Ronald
Wonderful South Maui Beach Condos
A beach with palm trees, rocks, and the ocean.

7. Awesome Maui Vista Beach Suite

Awesome Maui Vista Beach Suite
4.0 star property
South Kihei
8.6 out of 10, Excellent, (27 reviews)
"Absolutely perfect!!! Flavor of Hawaii!!"
United States
Laura
Awesome Maui Vista Beach Suite
A beach with clear blue water, rocky shore, and palm trees.

8. Condo w/ Lanai at Beginning of Road to Hana!

Condo w/ Lanai at Beginning of Road to Hana!
3.0 star property
Paia
The price is CA $236
CA $585 total
includes taxes & fees
Nov 13 - Nov 14
Condo w/ Lanai at Beginning of Road to Hana!
A tropical beach scene with palm trees, a clear blue sky, and a view of the ocean.

9. Waiohuli Beach Hale Ocean View Condos with Parking

Waiohuli Beach Hale Ocean View Condos with Parking
3.0 star property
Central Kihei
9.8 out of 10, Exceptional, (6 reviews)
"Easy access to the beach, nice kitchen, view of the water"
United States
Phillip J
The price is CA $281
CA $763 total
includes taxes & fees
Nov 11 - Nov 12
Waiohuli Beach Hale Ocean View Condos with Parking
A modern kitchen with a large island, a dining area with a view, and a living room with a sofa and chairs.

10. Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.6 out of 10, Exceptional, (54 reviews)
"Absolutely an amazing place. Very nice, clean, comfortable. We stayed in B104 and it is a perfect spot to get in and out. Definitely come back again."
United States
Angeline
The price is CA $250
CA $726 total
includes taxes & fees
Nov 15 - Nov 16
Kihei Ali'i Kai Condos with Free Parking
A modern living room with a sofa, coffee table, and a view of the ocean.

11. 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 CA $844
CA $1,448 total
includes taxes & fees
Nov 8 - Nov 9
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.
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Top Kailua Hotel Reviews

A wooden deck with a chair, surrounded by lush tropical vegetation and a clear blue sky.
Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
Haiku

10/10 Excellent

Everything was perfect!
Canada
Speranta
Reviewed February 12, 2026
Yonegan Maui Getaways - Haiku

Find out more about Kailua

Everything you need to know about Kailua vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kailua vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kailua vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kailua vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kailua vacation rentals we have selected for you start as low as CA $169 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kailua rentals

At Expedia, we put the best Kailua vacation 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 vacation.

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 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 Maui Garden Of Eden - Botanical Gardens & Arboretum and Makawao Park.

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.