Kailua Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Kailua holiday rentals

Beach towels

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (204 reviews)
"Recently renovated and spotless! This condo had everything we needed and was comfortable and conveniently located. Highly recommend!"
United States
Allison H.
The price is HK$1,450
HK$3,470 total
includes taxes & fees
2 May - 3 May
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Beach

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Hana Town Center
9.6 out of 10, Exceptional, (199 reviews)
"Had a very nice stay. The cottage was well equipped. I spent 8 days there. Loved this location in Hana."
United States
Lon S.
The price is HK$1,728
HK$3,786 total
includes taxes & fees
30 Apr - 1 May
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Sun-loungers, beach towels

[RARE] Upscale 2BR/2BA Kuau Paia - Walk to Beach

[RARE] Upscale 2BR/2BA Kuau Paia - Walk to Beach
Paia
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful Property"
United States
Kristin M.
The price is HK$2,212
HK$6,014 total
includes taxes & fees
2 May - 3 May
[RARE] Upscale 2BR/2BA Kuau Paia - Walk to Beach
Terrace/patio

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (30 reviews)
"The location was great, especially if you plan to see the whole island! Easy check in and check out. Clean place."
United States
Weronika
The price is HK$1,294
HK$2,712 total
includes taxes & fees
27 May - 28 May
Yonegan Maui Getaways - Haiku
TV

Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned
Paia
9.0 out of 10, Wonderful, (26 reviews)
"Clean and convenient"
United States
Ilya L
The price is HK$1,567
HK$2,774 total
includes taxes & fees
5 May - 6 May
Kuau Surf 2.0 Maui North Shore Locally-Owned
Exterior

Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.0 out of 10, Wonderful, (36 reviews)
"Great location, comfortable bed and room. "
United States
kimo
The price is HK$1,017
HK$2,480 total
includes taxes & fees
3 May - 4 May
Yonegan Maui Getaways - Haiku - Unit 6
Property grounds

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Kaʻeleku
9.8 out of 10, Exceptional, (243 reviews)
"30 yr anniversary - perfectly relaxing for us - would stay here again for sure."
United States
Trent H.
The price is HK$2,010
HK$4,208 total
includes taxes & fees
30 Apr - 1 May
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Beach towels

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Hana Town Center
9.6 out of 10, Exceptional, (446 reviews)
"Food truck near."
United States
Neal
The price is HK$1,528
HK$3,018 total
includes taxes & fees
14 May - 15 May
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
On the beach, sun-loungers, beach towels

Sugar Beach Resort Oceanview 1 bed/1 bath

Sugar Beach Resort Oceanview 1 bed/1 bath
North Kihei
9.6 out of 10, Exceptional, (117 reviews)
"Condo is fully stocked and decorated beautifully! "
United States
erin t.
The price is HK$1,171
HK$3,403 total
includes taxes & fees
30 Apr - 1 May
Sugar Beach Resort Oceanview 1 bed/1 bath
Interior

Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is HK$2,343
HK$4,967 total
includes taxes & fees
6 May - 7 May
Kuau Plaza Paia Condo with Parking
On the beach

Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Central Kihei
9.4 out of 10, Exceptional, (69 reviews)
"The room was perfect! "
United States
Gillian
The price is HK$1,011
HK$2,924 total
includes taxes & fees
22 May - 23 May
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Beach towels

Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.6 out of 10, Exceptional, (426 reviews)
"Very peaceful place to stay. Enjoyed location and would stay again if I come to Hana!"
United States
Nicholas
The price is HK$1,528
HK$3,174 total
includes taxes & fees
25 May - 26 May
Fisher's Hana Bay Hale, Across from Hana Bay
Travel cot, free WiFi, bed sheets

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
North Kihei
9.0 out of 10, Wonderful, (7 reviews)
"Great stay, clean place. Close walk to the beach. The pool and hot tub were great and well taken care of"
United States
Danniella
The price is HK$741
HK$2,740 total
includes taxes & fees
3 May - 4 May
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
Terrace/patio

Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (55 reviews)
"Great location and comfy!"
United States
Lindsay B.
The price is HK$1,474
HK$2,735 total
includes taxes & fees
12 May - 13 May
Stay in Hana #2
Property grounds

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (77 reviews)
"Great view, excellent location. 2 -3 nights is the perfect amount of time in Hana."
United States
Jim
The price is HK$2,829
HK$4,001 total
includes taxes & fees
30 Apr - 1 May
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Interior

Kuau Surf North shore Maui Locally-Owned

Kuau Surf North shore Maui Locally-Owned
Paia
9.0 out of 10, Wonderful, (39 reviews)
"Cute clean and a short couple minute walk to the beach where their was seaturtles waiting "
United States
Bobby
The price is HK$1,489
HK$2,688 total
includes taxes & fees
5 May - 6 May
Kuau Surf North shore Maui Locally-Owned
Property grounds

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (101 reviews)
"This bungalow is perfect! It is beautiful and peaceful. I would come to Hāna just to stay here. And the host provided excellent information and was very gracious. "
United States
Catherine R.
The price is HK$2,429
HK$4,273 total
includes taxes & fees
10 May - 11 May
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Beach

Unit 23 Waena Inn - Maui Private Suite

Unit 23 Waena Inn - Maui Private Suite
Wailuku
10.0 out of 10, Exceptional, (11 reviews)
"Fairly central location. Helpful and due to the length of our stay, offered for us to use washer/dryer, snorkels, beach towels. "
United States
Suzan F.
The price is HK$1,762
HK$2,653 total
includes taxes & fees
7 May - 8 May
Unit 23 Waena Inn - Maui Private Suite
Property grounds

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Hana Town Center
9.6 out of 10, Exceptional, (27 reviews)
"I would stay again "
United States
Bruce H.
The price is HK$2,852
HK$3,988 total
includes taxes & fees
5 May - 6 May
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
A heated pool

GREAT RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.

GREAT RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.
North Kihei
9.4 out of 10, Exceptional, (77 reviews)
"The room was adequate for our needs. Communication with the host was good. The room could use a deep clean and some items are in need of replacement. We loved Sugar Beach and the ease of access to many things to do. The hot tub was luke warm several nights when we went to use it. We had a great time and enjoyed ourselves. "
United States
Stacy O.
The price is HK$1,192
HK$3,732 total
includes taxes & fees
10 May - 11 May
GREAT RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.
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

Hampton Inn & Suites Maui North Shore

Hampton Inn & Suites Maui North Shore

10/10 Excellent
"Beautiful rooms. The view is nice also. We were out exploring the island everyday. Would definitely stay here again."
Tabitha Sarah 7-night trip
Posted 7 hours ago
Hampton Inn & Suites Maui North Shore

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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Frequently asked questions

Can I find a holiday rental in Kailua?

Yes, there are holiday rentals close to the most popular sights in Kailua, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Kailua has to offer?

Yonegan Maui Getaways - Haiku : This holiday home rental outside of Kailua is located near the beach, and has 1 hot tub, a BBQ 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 wider area, you’ll find Twin Falls and Maui Garden Of Eden - Botanical Gardens & Arboretum.

What’s a holiday rental in Kailua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kailua. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a small group gathering.