An aerial view of a coastal town with clear turquoise waters, two prominent islands, and lush green hills.

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Our top choices for Kailua holiday rentals

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!
Hana
10.0 out of 10, Exceptional, (515 reviews)
"Beautiful place. Excellent host. "
United States
Darryl S.
The price is £335
includes taxes & fees
28 Jun - 29 Jun
Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!

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, (455 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is £292
includes taxes & fees
10 Jul - 11 Jul
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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, (211 reviews)
"Great location near Paia shops and short walk to Mama's Fish House, & beach. Enjoyed our stay at Kuau Plaza. The condo was just as described and pictured. Nicely furnished & decorated. Comfy bed, everything you could need in the kitchen, nice bathroom...all looked brand new! Although right next to the road, we barely heard the traffic. We would stay here again."
United States
Kimberly
The price is £332
includes taxes & fees
16 Jul - 17 Jul
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

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, (439 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is £308
includes taxes & fees
10 Jul - 11 Jul
Fisher's Hana Bay Hale, Across from Hana Bay

Oceanview Condo in Hana-Let the ocean lull you to sleep

Oceanview Condo in Hana-Let the ocean lull you to sleep
Hana Town Center
9.2 out of 10, Wonderful, (146 reviews)
"Nice location, comfortable accommodations. We loved the view off the lanai. "
United States
Kelly J.
The price is £345
includes taxes & fees
4 Jul - 5 Jul
Oceanview Condo in Hana-Let the ocean lull you to sleep

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, (158 reviews)
"The host communicated clearly and the accommodations were exactly what we were looking for. "
United States
Angie F.
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (38 reviews)
"Everything was great."
United States
Bryan
The price is £237
includes taxes & fees
23 Jun - 24 Jun
Yonegan Maui Getaways - Haiku - Unit 6

Sugar Beach 314 Front Row Ocean Views in Beautifully Upgraded Beachfront Condo

Sugar Beach 314 Front Row Ocean Views in Beautifully Upgraded Beachfront Condo
North Kihei
9.6 out of 10, Exceptional, (57 reviews)
"This is a great unit. Excellent location and easy access to everything on Maui. "
United States
scott s.
The price is £427
includes taxes & fees
22 Jun - 23 Jun
Sugar Beach 314 Front Row Ocean Views in Beautifully Upgraded Beachfront Condo

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 £366
includes taxes & fees
22 Jun - 23 Jun
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

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, (9 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 £255
includes taxes & fees
12 Jul - 13 Jul
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood

Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood
Paia
10.0 out of 10, Exceptional, (12 reviews)
"We had a wonderful stay, our host was sweet"
United States
Nancy k.
The price is £300
includes taxes & fees
23 Jun - 24 Jun
Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
North Kihei
9.8 out of 10, Exceptional, (29 reviews)
"Nice place"
Canada
PC SHOP
The price is £355
includes taxes & fees
23 Jun - 24 Jun
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

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 £427
includes taxes & fees
25 Jun - 26 Jun
The Ocean View Residence

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)
"Beautiful grounds, great location close to secluded beach."
United States
Mark S.
The price is £414
includes taxes & fees
2 Jul - 3 Jul
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Unit 25 Waena Inn - Maui Private Suite

Unit 25 Waena Inn - Maui Private Suite
Wailuku
9.8 out of 10, Exceptional, (16 reviews)
"Had a great time, even with the rain ."
United States
Kevin M.
The price is £222
includes taxes & fees
22 Jun - 23 Jun
Unit 25 Waena Inn - Maui Private Suite

Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
9.0 out of 10, Wonderful, (21 reviews)
"Great location for driving the Road to Hana."
United States
Lisa
The price is £263
includes taxes & fees
24 Jun - 25 Jun
Yonegan Maui Getaways - Haiku - Unit 4

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, (247 reviews)
"I appreciated everything as advertised. Would have preferred mini splits or AC in the bedrooms, but still a nice peaceful spot."
United States
Robert
The price is £503
includes taxes & fees
14 Jul - 15 Jul
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Steps to the Beach, Affordable w/Free Parking

Steps to the Beach, Affordable w/Free Parking
North Kihei
9.6 out of 10, Exceptional, (171 reviews)
"Clean, across the street from beach and whale center. Great location to get to other places on the island. "
Canada
wayneiversonphotosk
The price is £330
includes taxes & fees
22 Jun - 23 Jun
Steps to the Beach, Affordable w/Free Parking

Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (63 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is £337
includes taxes & fees
25 Jun - 26 Jun
Hale Nihi - Paia, Maui

Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023

Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023
Central Kihei
10.0 out of 10, Exceptional, (113 reviews)
"Beautiful views, lovely beach, convenient parking and good amenities nearby. "
United States
Tesha T.
The price is £355
includes taxes & fees
23 Jun - 24 Jun
Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023
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 Haleakala National Park. In the wider area, you’ll find Garden of Eden Arboretum 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.