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
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 NT$4,633
NT$10,425 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 NT$18,872
NT$41,010 total
includes taxes & fees
Nov 30 - Dec 1
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
A modern living room with a large TV, a ceiling fan, and a view of palm trees through large windows.

3. Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is NT$16,908
NT$31,726 total
includes taxes & fees
Nov 17 - Nov 18
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 NT$3,989
NT$22,208 total
includes taxes & fees
Nov 11 - Nov 12
The Ocean View Residence
A balcony with a table set for breakfast, overlooking a scenic view with palm trees and the ocean.

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$5,910
NT$26,270 total
includes taxes & fees
Nov 13 - Nov 14
The Kalama Residence
A beachfront hotel with palm trees, a grassy lawn, and a view of the ocean.

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 modern kitchen with wooden cabinets, a central island, and a dining area with a table and chairs.

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 tropical resort with a paved pathway, palm trees, and a building with a curved roof.

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 NT$5,549
NT$13,739 total
includes taxes & fees
Nov 12 - Nov 13
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 NT$6,599
NT$17,929 total
includes taxes & fees
Nov 18 - Nov 19
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 NT$6,192
NT$17,477 total
includes taxes & fees
Nov 13 - Nov 14
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 NT$19,831
NT$34,026 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

Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

10/10 Excellent
"Hilton Grand Vacations Club Maui Bay Villas is an exceptional beautiful property with a great room layout and upscale furnishings that make you feel like you’re staying somewhere special. The staff was very helpful with expedient chech-in/check-out, detailed information about property layout, services, and other amenities available. HBVC has pride in their property as the grounds themselves are beautifully maintained with the several pools, waterfalls and an adequate gym. Plus, the property is walking distance from the beach."
Robert Earl Prather 6-night trip
Posted 1 day ago
Hilton Grand Vacations Club Maui Bay Villas

Find out more about Kailua

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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.