Kailua Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Kailua holiday rentals

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$1,400
HK$3,384 total
includes taxes & fees
30 Mar - 31 Mar
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Terrace/patio

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (29 reviews)
"Everything was perfect!"
Canada
Speranta
The price is HK$1,381
HK$2,813 total
includes taxes & fees
14 Apr - 15 Apr
Yonegan Maui Getaways - Haiku
Sun-loungers, beach towels

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Hana Town Center
9.2 out of 10, Wonderful, (154 reviews)
"The location was fantastic and the house was very comfortable, especially the beds."
United States
Lisa H.
The price is HK$1,754
HK$4,020 total
includes taxes & fees
29 Mar - 30 Mar
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
On the beach

Embark on a journey through Maui with Aloha Glamp

Embark on a journey through Maui with Aloha Glamp
Haiku-Pauwela
9.6 out of 10, Exceptional, (41 reviews)
"He had everything for our camping, great experience "
United States
Zuka C.
The price is HK$872
HK$2,210 total
includes taxes & fees
31 Mar - 1 Apr
Embark on a journey through Maui with Aloha Glamp
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
9.8 out of 10, Exceptional, (26 reviews)
"I would stay again "
United States
Bruce H.
The price is HK$2,693
HK$3,806 total
includes taxes & fees
28 Mar - 29 Mar
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
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, (201 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$1,446
HK$3,486 total
includes taxes & fees
20 Apr - 21 Apr
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
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, (436 reviews)
"Enjoyed the screened in porch"
United States
Thomas
The price is HK$1,525
HK$3,027 total
includes taxes & fees
24 Apr - 25 Apr
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Property grounds

Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!

Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!
Hana Town Center
9.8 out of 10, Exceptional, (84 reviews)
"The location was very good."
United States
Jim B.
The price is HK$2,779
HK$3,974 total
includes taxes & fees
1 Apr - 2 Apr
Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!
Exterior

Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (35 reviews)
"Great location, comfortable bed and room. "
United States
kimo
The price is HK$1,084
HK$2,584 total
includes taxes & fees
20 Apr - 21 Apr
Yonegan Maui Getaways - Haiku - Unit 6
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$761
HK$2,751 total
includes taxes & fees
27 Mar - 28 Mar
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
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
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Sun-loungers, beach towels

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
North Kihei
9.8 out of 10, Exceptional, (109 reviews)
"This place was in a good location in Kihei. You are within 5 mins of dozen of beaches. All the beach gear a person needs is provided(towels, chairs, snorkels, flippers, coolers and more)! Jon is super friendly and a great host!"
United States
Troy s.
The price is HK$647
HK$3,681 total
includes taxes & fees
27 Mar - 28 Mar
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
Dining room

The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is HK$814
HK$4,992 total
includes taxes & fees
14 Apr - 15 Apr
The Ocean View Residence
Interior

Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is HK$2,470
HK$5,114 total
includes taxes & fees
28 Mar - 29 Mar
Kuau Plaza Paia Condo with Parking
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, (239 reviews)
"30 yr anniversary - perfectly relaxing for us - would stay here again for sure."
United States
Trent H.
The price is HK$2,357
HK$4,722 total
includes taxes & fees
6 Apr - 7 Apr
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Terrace/patio

Ground floor oceanfront, walk out to beach

Ground floor oceanfront, walk out to beach
Central Kihei
9.0 out of 10, Wonderful, (37 reviews)
"Great location and beautiful beach"
United States
Stephanie M.
The price is HK$837
HK$5,109 total
includes taxes & fees
3 Apr - 4 Apr
Ground floor oceanfront, walk out to beach
On the beach, sun-loungers, beach towels

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
North Kihei
9.6 out of 10, Exceptional, (15 reviews)
"Perfect ocean views for morning coffee. Close to all the restaurants and good beaches "
United States
Michael A.
The price is HK$1,095
HK$3,486 total
includes taxes & fees
6 Apr - 7 Apr
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
Beach

Unit 23 Waena Inn - Maui Private Suite

Unit 23 Waena Inn - Maui Private Suite
Wailuku
10.0 out of 10, Exceptional, (10 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$1,751
HK$2,609 total
includes taxes & fees
28 Mar - 29 Mar
Unit 23 Waena Inn - Maui Private Suite
TV

Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned
Paia
9.2 out of 10, Wonderful, (23 reviews)
"Clean and convenient"
United States
Ilya L
The price is HK$1,720
HK$2,957 total
includes taxes & fees
20 Apr - 21 Apr
Kuau Surf 2.0 Maui North Shore Locally-Owned
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 Sunset

Maui Sunset

10/10 Excellent
"The kids loved the pool, our room was clean and the grounds were beautiful!"
mollie 6-night trip
Posted 10 hours ago
Maui Sunset

Find out more about Kailua

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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, kitchenware and a coffee maker.

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.