Holiday Rentals in Kailua

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Our top choices for Kailua holiday rentals

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (18 reviews)
"It is a cozy place. It has all the amenities. It feels like home"
United States
Roberto
The price is €240
includes taxes & fees
28 Jan - 29 Jan
Yonegan Maui Getaways - Haiku

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, (192 reviews)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
The price is €427
includes taxes & fees
15 Jan - 16 Jan
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

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, (196 reviews)
"Very quiet safe place. "
Canada
Monica
The price is €378
includes taxes & fees
15 Jan - 16 Jan
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi

Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi
Paia
9.8 out of 10, Exceptional, (90 reviews)
"Really nice, conveniently located within walking distance to Paia.."
United States
Phil B.
The price is €418
includes taxes & fees
31 Jan - 1 Feb
Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi

BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach
North Kihei
10.0 out of 10, Exceptional, (130 reviews)
"Very nice condo Nice furniture Comfortable and friendly "
United States
John
The price is €322
includes taxes & fees
29 Jan - 30 Jan
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

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, (417 reviews)
"We were only able to stay one night, but we loved it and definitely plan on going back!!"
United States
Trista B.
The price is €314
includes taxes & fees
24 Jan - 25 Jan
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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, (412 reviews)
"Great location"
United States
peter
The price is €350
includes taxes & fees
24 Jan - 25 Jan
Fisher's Hana Bay Hale, Across from Hana Bay

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hana
10.0 out of 10, Exceptional, (91 reviews)
"Very unique property near Hana. Great experience!"
United States
Keith R.
The price is €496
includes taxes & fees
19 Jan - 20 Jan
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Ai Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!

Ai Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!
North Kihei
9.6 out of 10, Exceptional, (287 reviews)
"Great room, affordable, clean, sufficient, well maintained, easy access"
United States
John K.
The price is €332
includes taxes & fees
17 Jan - 18 Jan
Ai Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!

Stay in Hana Upstairs

Stay in Hana Upstairs
Hana Town Center
9.8 out of 10, Exceptional, (34 reviews)
"Lovely place in a lush jungle. "
United States
Heather T.
The price is €419
includes taxes & fees
15 Jan - 16 Jan
Stay in Hana Upstairs

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
9.4 out of 10, Exceptional, (147 reviews)
"Great space. Centrally located with easy proximity to food & groceries. Perfect for our needs. Comfy bed too. "
United States
Tracy A.
The price is €493
includes taxes & fees
16 Jan - 17 Jan
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Seaside Escape Just steps to the Beach!

Seaside Escape Just steps to the Beach!
2.0 star property
North Kihei
10.0 out of 10, Exceptional, (3 reviews)
"Room was very nice "
United States
nathan
The price is €295
includes taxes & fees
10 Feb - 11 Feb
Seaside Escape Just steps to the Beach!

Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
8.6 out of 10, Excellent, (15 reviews)
"The property was strategically located near the Road to Hana and Haleakala National Park."
United States
C T.
Yonegan Maui Getaways - Haiku - Unit 4

Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm
Kaʻeleku
9.4 out of 10, Exceptional, (281 reviews)
"This was a great location, comfortable cute little cottage."
United States
Briana B.
The price is €486
includes taxes & fees
2 Feb - 3 Feb
Secluded cottage on Tropical flower farm

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, (59 reviews)
"The room was perfect! "
United States
Gillian
The price is €318
includes taxes & fees
22 Jan - 23 Jan
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

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, (83 reviews)
"The location was very good."
United States
Jim B.
The price is €486
includes taxes & fees
18 Jan - 19 Jan
Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (268 reviews)
"Great stay"
United States
Noah C.
The price is €366
includes taxes & fees
18 Jan - 19 Jan
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

OCEANFRONT RESORT- It's Whale Season -Kihei Sands Beachfront Condo-A12

OCEANFRONT RESORT- It's Whale Season -Kihei Sands Beachfront Condo-A12
North Kihei
9.2 out of 10, Wonderful, (69 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: had a great time with no problems"
United States
Dave & Pam C.
OCEANFRONT RESORT- It's Whale Season -Kihei Sands Beachfront Condo-A12

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.0 out of 10, Wonderful, (21 reviews)
"I loved that it was a short walk to the beach and there were grocery stores nearby. Lots of options of places to eat and shop and explore the island!"
United States
Emma
Kihei Ali'i Kai Condos with Free Parking

Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!

Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!
Central Kihei
9.4 out of 10, Exceptional, (85 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful condo, great views and location"
United States
Pam B.
The price is €529
includes taxes & fees
28 Jan - 29 Jan
Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!
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

Find out more about Kailua

Everything you need to know about Kailua holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kailua holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kailua holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kailua holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kailua. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kailua holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kailua holiday rentals we have selected for you start as low as €240 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kailua rentals

At Expedia, we put the best Kailua holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Kailua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kailua holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kailua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Garden of Eden Arboretum. In the wider area, you’ll find Maui Garden Of Eden - Botanical Gardens & Arboretum and Maui Spa Retreat.

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.