An aerial view of a coastal town with clear turquoise waters, two prominent islands, and lush green hills.

Kailua Vacation Rentals

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Our top choices for Kailua vacation rentals

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (37 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is CA $177
CA $420 total
includes taxes & fees
Oct 4 - Oct 5
Yonegan Maui Getaways - Haiku

2. Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is CA $720
CA $1,352 total
includes taxes & fees
Sep 28 - Sep 29
Kuau Plaza Paia Condo with Parking

3. 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 $237
CA $587 total
includes taxes & fees
Oct 5 - Oct 6
Condo w/ Lanai at Beginning of Road to Hana!

4. The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (2 reviews)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is CA $105
CA $808 total
includes taxes & fees
Sep 23 - Sep 24
The Ocean View Residence

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 $536
CA $1,727 total
includes taxes & fees
Sep 23 - Sep 24
The Kalama Residence

6. Kauhale Makai by Coldwell Banker Island Vacations

Kauhale Makai by Coldwell Banker Island Vacations
3.0 star property
Central Kihei
8.0 out of 10, Very good, (1 review)
"Stayed in Kauhale Makai 102 for 7 nights. A few suggestions: -since it is a studio, consider upgrading the refrigerator to a quieter model that does't sound like a noisy engine running right next to you ! - the mattress needs replacing, very saggy in the middle and way too soft"
United States
petru
The price is CA $236
CA $1,404 total
includes taxes & fees
Sep 23 - Sep 24
Kauhale Makai by Coldwell Banker Island Vacations

7. 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 $919
CA $1,538 total
includes taxes & fees
Sep 24 - Sep 25
2BR/2BA Oceanfront Condo in Maui Sunset

8. 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 $764 total
includes taxes & fees
Oct 1 - Oct 2
Waiohuli Beach Hale Ocean View Condos with Parking

9. 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 $248
CA $726 total
includes taxes & fees
Sep 23 - Sep 24
Kihei Ali'i Kai Condos with Free Parking

10. Ocean-view Kihei Condo w/ Lanai: Steps to Beach!

Ocean-view Kihei Condo w/ Lanai: Steps to Beach!
3.0 star property
North Kihei
The price is CA $314
CA $1,086 total
includes taxes & fees
Sep 25 - Sep 26
Ocean-view Kihei Condo w/ Lanai: Steps to Beach!

11. Lanai & Steps to Beach! Stunning South Maui Condo

Lanai & Steps to Beach! Stunning South Maui Condo
3.5 star property
North Kihei
The price is CA $330
CA $697 total
includes taxes & fees
Oct 15 - Oct 16
Lanai & Steps to Beach! Stunning South Maui 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.
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Top Kailua Hotel Reviews

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 $420 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 Maui Spa Retreat.

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.