Kailua Holiday Rentals

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Our top choices for Kailua holiday rentals

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 NZ$603
includes taxes & fees
14 Apr - 15 Apr
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Luxury Ocean Front Living -- 180 Degree Direct Ocean View -- Best in Kihei

Luxury Ocean Front Living -- 180 Degree Direct Ocean View -- Best in Kihei
North Kihei
9.8 out of 10, Exceptional, (120 reviews)
"Nice relaxing beautiful stay. Ocean and accommodations were wonderful. "
United States
Jeff I.
The price is NZ$665
includes taxes & fees
12 Apr - 13 Apr
Luxury Ocean Front Living -- 180 Degree Direct Ocean View -- Best in Kihei

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (305 reviews)
"Super cute place to stay and the host was very helpful. Great location on the island and everything was super clean and easy to use. Best place to stay!!!!"
United States
Anonymous traveller
The price is NZ$653
includes taxes & fees
11 Apr - 12 Apr
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

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 NZ$614
includes taxes & fees
13 Apr - 14 Apr
Yonegan Maui Getaways - Haiku

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 NZ$555
includes taxes & fees
13 Apr - 14 Apr
Yonegan Maui Getaways - Haiku - Unit 6

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 NZ$844
includes taxes & fees
21 Apr - 22 Apr
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

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, (273 reviews)
"Perfectly situated on Maui island to easily visit everything and come back to condo to sleep."
Canada
Jean-Philippe R.
The price is NZ$669
includes taxes & fees
21 Apr - 22 Apr
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

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
9.6 out of 10, Exceptional, (297 reviews)
"Kevin was great host ,the place was very clean right across the beach with lots of turtles everyday and everything we needed!I will recommend this place for everyone and special for families with young kids because across the street is an Hawaiian Pond with shallow water on one side that the kids can walk all the way to the rocks and observe the turtles up close!"
United States
Roula
The price is NZ$682
includes taxes & fees
27 Apr - 28 Apr
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is NZ$1,194
includes taxes & fees
15 Apr - 16 Apr
Kuau Plaza Paia Condo with Parking

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, (202 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 NZ$751
includes taxes & fees
11 Apr - 12 Apr
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Stunning South Maui Condo w/ Lanai by Beach!

Stunning South Maui Condo w/ Lanai by Beach!
North Kihei
9.8 out of 10, Exceptional, (31 reviews)
"The place was clean, quiet, and relaxing. Steps away to the beach where you can see sea turtles every evening around sunset."
United States
Sachie
The price is NZ$652
includes taxes & fees
16 Apr - 17 Apr
Stunning South Maui Condo w/ Lanai by Beach!

Great location between Hana Town and Hamoa Beach, private, family-friendly

Great location between Hana Town and Hamoa Beach, private, family-friendly
Hana Town Center
9.8 out of 10, Exceptional, (236 reviews)
"Good location & great experience"
United States
Hengqun S.
The price is NZ$873
includes taxes & fees
7 May - 8 May
Great location between Hana Town and Hamoa Beach, private, family-friendly

Unit 15 Waena Inn - Maui Private Suite

Unit 15 Waena Inn - Maui Private Suite
Wailuku
9.4 out of 10, Exceptional, (28 reviews)
"Good place to stay"
United States
Ram
The price is NZ$580
includes taxes & fees
11 Apr - 12 Apr
Unit 15 Waena Inn - Maui Private Suite

Steps to the Beach, Affordable w/Free Parking

Steps to the Beach, Affordable w/Free Parking
North Kihei
9.6 out of 10, Exceptional, (169 reviews)
"It was a great place to stay in Maui. It was away from the busy area in Kihea and across the street from a small beach. Only issue was finding the unit in the evening because of the lighting. We were able to see the sunrise from the bedroom window then walk across to see the sunset!"
United States
H K.
The price is NZ$770
includes taxes & fees
5 May - 6 May
Steps to the Beach, Affordable w/Free Parking

Oceanfront, Million-Dollar-View, B421

Oceanfront, Million-Dollar-View, B421
Central Kihei
10.0 out of 10, Exceptional, (193 reviews)
"We greatly enjoyed our stay at the condo. Everything was very clean, and the condo was extremely well stocked with kitchen items and water supplies. The views were stunning, and our family of 6 had an amazing stay! "
United States
Maureen G.
Oceanfront, Million-Dollar-View, B421

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 NZ$1,199
includes taxes & fees
14 Apr - 15 Apr
The Kalama Residence

Kuau Surf North shore Maui Locally-Owned

Kuau Surf North shore Maui Locally-Owned
Paia
9.0 out of 10, Wonderful, (38 reviews)
"Cute clean and a short couple minute walk to the beach where their was seaturtles waiting "
United States
Bobby
The price is NZ$585
includes taxes & fees
15 Apr - 16 Apr
Kuau Surf North shore Maui Locally-Owned

Maui Vista condo, in the heart of Kihei!

Maui Vista condo, in the heart of Kihei!
South Kihei
9.4 out of 10, Exceptional, (155 reviews)
"Amazing location. Beach right across the street. Great restaurants and shopping within easy walking distance. Only issue with stay that did not bother us at all but may be an issue for someone else is that the air conditioning in the front living room did not cool the space. Air conditioner in the bedroom worked great. "
United States
sigrid s.
The price is NZ$712
includes taxes & fees
21 Apr - 22 Apr
Maui Vista condo, in the heart of Kihei!

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (99 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 NZ$913
includes taxes & fees
22 Apr - 23 Apr
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
North Kihei
10.0 out of 10, Exceptional, (39 reviews)
"we really enjoyed our stay here. It is clean and maintained well and close to the beach."
United States
stuti s.
The price is NZ$798
includes taxes & fees
15 Apr - 16 Apr
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
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, 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 NZ$492 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 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.