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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (39 reviews)
"Rooms were very comfortable and clean. Super easy check in and out. Great location, not touristy at all, which is what I like for a vacation! Great staff made everything super easygoing. Will definitely be back!"
United States
Jennifer
The price is ￥22,308
￥50,194 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥90,591
￥196,855 total
includes taxes & fees
Oct 31 - Nov 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 ￥81,411
￥152,755 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥14,540
￥96,760 total
includes taxes & fees
Nov 13 - Nov 14
The Ocean View Residence
A beach with clear turquoise water, a sandy shore, and a distant mountain.

5. Wonderful South Maui Beach Condos

Wonderful South Maui Beach Condos
3.5 star property
South Kihei
9.2 out of 10, Wonderful, (44 reviews)
"Great location, perfect for my trip. "
United States
John
The price is ￥33,861
￥77,541 total
includes taxes & fees
Nov 1 - Nov 2
Wonderful South Maui Beach Condos
A beach with clear blue water, a sandy shore, and palm trees.

6. 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 ￥25,470
￥120,113 total
includes taxes & fees
Oct 19 - Oct 20
The Kalama Residence
A modern living room with a sofa, coffee table, and a wooden entertainment unit.

7. Kihei Garden Estates B-103 - Modern Design, Bright & Clean, Concrete Floors, AC!

Kihei Garden Estates B-103 - Modern Design, Bright & Clean, Concrete Floors, AC!
3.5 star property
Central Kihei
Kihei Garden Estates B-103 - Modern Design, Bright & Clean, Concrete Floors, AC!
A beach with palm trees, rocks, and the ocean.

8. 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
The price is ￥34,994
￥78,892 total
includes taxes & fees
Nov 1 - Nov 2
Awesome Maui Vista Beach Suite
A beach with clear blue water, rocky shore, and palm trees.

9. 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 ￥26,716
￥66,149 total
includes taxes & fees
Nov 1 - Nov 2
Condo w/ Lanai at Beginning of Road to Hana!
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 ￥29,723
￥83,894 total
includes taxes & fees
Oct 17 - Oct 18
Kihei Ali'i Kai Condos with Free Parking
A tropical beach scene with palm trees, a clear blue sky, and a view of the ocean.

11. 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 ￥31,778
￥86,333 total
includes taxes & fees
Oct 22 - Oct 23
Waiohuli Beach Hale Ocean View Condos with Parking
An aerial view of a beach with clear turquoise water, sandy shore, and scattered umbrellas.

12. Island Surf 304 - Modern Renovation, Must See Ocean View, Cool Split AC, Wi-fi !

Island Surf 304 - Modern Renovation, Must See Ocean View, Cool Split AC, Wi-fi !
2.0 star property
South Kihei
The price is ￥29,705
￥95,134 total
includes taxes & fees
Oct 29 - Oct 30
Island Surf 304 - Modern Renovation, Must See Ocean View, Cool Split AC, Wi-fi !
A modern living room with a sofa, coffee table, and a view of the ocean.

13. 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 ￥95,492
￥163,847 total
includes taxes & fees
Oct 24 - Oct 25
2BR/2BA Oceanfront Condo in Maui Sunset
A beach with a building on the left, a rocky breakwater, and a clear blue sky.

14. 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 ￥37,312
￥78,733 total
includes taxes & fees
Nov 1 - Nov 2
Lanai & Steps to Beach! Stunning South Maui Condo
A tennis court with a net, surrounded by palm trees and a building with multiple balconies.

15. Shores of Maui 215 - Dramatic Ocean Views, Steps to the Beach, Renovated, AC!

Shores of Maui 215 - Dramatic Ocean Views, Steps to the Beach, Renovated, AC!
3.5 star property
South Kihei
Shores of Maui 215 - Dramatic Ocean Views, Steps to the Beach, Renovated, AC!
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

Hana-Maui Resort, a Destination by Hyatt Residence

Hana-Maui Resort, a Destination by Hyatt Residence

10/10 Excellent
"Room was very large and slightly dated but clean and comfortable. Lyman was courteous, helpful, friendly and went out of his way to accommodate our stay. Chelsea also was extremely friendly, accommodating and always smiling! Breakfast was delicious, the fruit plate especially!"
Terry 1-night trip
Posted 9 hours ago
Hana-Maui Resort, a Destination by Hyatt Residence

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.