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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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Kailua vacation rentals

Studio, Garden View (Haiku #6) | Terrace/patio

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 NT$4,016
NT$9,530 total
includes taxes & fees
Oct 4 - Oct 5
Yonegan Maui Getaways - Haiku
Interior

2. Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is NT$16,352
NT$30,682 total
includes taxes & fees
Sep 30 - Oct 1
Kuau Plaza Paia Condo with Parking
Apartment (1 Bedroom) | Interior

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 NT$5,366
NT$13,287 total
includes taxes & fees
Oct 5 - Oct 6
Condo w/ Lanai at Beginning of Road to Hana!
Elite Apartment, Balcony, Ocean View | Dining room

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 NT$2,367
NT$18,251 total
includes taxes & fees
Sep 26 - Sep 27
The Ocean View Residence
On the beach, white sand

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 NT$8,787
NT$31,970 total
includes taxes & fees
Sep 23 - Sep 24
The Kalama Residence
Condo, 1 Bedroom | Property grounds

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 NT$5,408
NT$31,917 total
includes taxes & fees
Sep 23 - Sep 24
Kauhale Makai by Coldwell Banker Island Vacations
Family Apartment, 2 Bedrooms, 2 Bathrooms, Ocean View (1015) | Living area | 50-inch TV with digital channels

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 NT$20,861
NT$34,904 total
includes taxes & fees
Oct 1 - Oct 2
2BR/2BA Oceanfront Condo in Maui Sunset
On the beach, white sand, beach towels

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 NT$6,382
NT$17,339 total
includes taxes & fees
Sep 25 - Sep 26
Waiohuli Beach Hale Ocean View Condos with Parking
Family Apartment, 1 King Bed with Sofa bed, Garden View (1 BR 1011) | Living area

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 NT$5,969
NT$16,849 total
includes taxes & fees
Sep 23 - Sep 24
Kihei Ali'i Kai Condos with Free Parking
Apartment (2 Bedrooms) | Front of property

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 NT$7,112
NT$24,582 total
includes taxes & fees
Sep 25 - Sep 26
Ocean-view Kihei Condo w/ Lanai: Steps to Beach!
Apartment (1 Bedroom) | Interior

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 NT$7,510
NT$15,848 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

Maui Beach Vacation Club

Maui Beach Vacation Club

10/10 Excellent
"Loved this place! We had a ground floor with patio facing the pool. Just lovely. Ocean across the street."
Richard Jay 7-night trip
Posted 5 hours ago
Maui Beach Vacation Club

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:

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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 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.