Kailua Holiday Rentals

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Our top choices for Kailua holiday rentals

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, (129)
"Very nice condo Nice furniture Comfortable and friendly "
United States
John
The price is NZ$579
includes taxes & fees
29 Jan - 30 Jan
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

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
9.8 out of 10, Exceptional, (298)
"Great place to stay! I would stay again. Has everything you need and a pool and hot tub!"
Canada
Mary F.
The price is NZ$689
includes taxes & fees
5 Jan - 6 Jan
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

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)
"Great room, affordable, clean, sufficient, well maintained, easy access"
United States
John K.
The price is NZ$655
includes taxes & fees
5 Jan - 6 Jan
AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (16)
"It is a cozy place. It has all the amenities. It feels like home"
United States
Roberto
The price is NZ$486
includes taxes & fees
5 Jan - 6 Jan
Yonegan Maui Getaways - Haiku

Modern Kihei Resort 2 Bedroom, 2 Bath Condo with AC - Steps to the Beach

Modern Kihei Resort 2 Bedroom, 2 Bath Condo with AC - Steps to the Beach
North Kihei
10.0 out of 10, Exceptional, (31)
"Clean- easy access- close to town- enjoyed our time there- mahalo!"
United States
Melodie V.
The price is NZ$1,041
includes taxes & fees
5 Jan - 6 Jan
Modern Kihei Resort 2 Bedroom, 2 Bath Condo with AC - Steps to the Beach

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, (12)
"Wonderful place to stay. Awesome host. We had a great time and hopefully be back soon!"
United States
Jennifer D.
The price is NZ$779
includes taxes & fees
28 Jan - 29 Jan
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

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)
"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

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, (410)
"Great location for a Hana to Ka'anapali trip. "
United States
Anonymous traveller
The price is NZ$692
includes taxes & fees
24 Jan - 25 Jan
Fisher's Hana Bay Hale, Across from Hana Bay

Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental

Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental
4.0 star property
South Kihei
9.6 out of 10, Exceptional, (48)
"Good location near beach with AC in each room, many beds were good for a larger group."
Canada
Daniel C.
The price is NZ$899
includes taxes & fees
27 Jan - 28 Jan
Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental

Stay in Hana #1

Stay in Hana #1
Hana Town Center
8.8 out of 10, Excellent, (60)
"Inflexible host"
United States
Nagender
The price is NZ$607
includes taxes & fees
12 Jan - 13 Jan
Stay in Hana #1

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, (38)
"We booked this Jeep for our honeymoon stay on Maui. It was a wonderful drive, handled every road we were on beautiful, and provided a great place to sleep. Sebastian had all the necessities packed and it made for an easy trip. Couldn’t be happier. "
United States
Sage B.
The price is NZ$531
includes taxes & fees
13 Jan - 14 Jan
Embark on a journey through Maui with Aloha Glamp

Ocean View Studio Steps to Beach - Pool, Spa & Pickleball - Free parking & Wi-Fi

Ocean View Studio Steps to Beach - Pool, Spa & Pickleball - Free parking & Wi-Fi
North Kihei
8.8 out of 10, Excellent, (89)
"We had a great stay. It was the perfect central location to get around Maui. It’s a little noisy being right on the main Kihei road but other than that it’s a perfect place! "
United States
Matthan G.
Ocean View Studio Steps to Beach - Pool, Spa & Pickleball - Free parking & Wi-Fi

Oceanfront penthouse with amazing views at Kauhale Makai

Oceanfront penthouse with amazing views at Kauhale Makai
Central Kihei
9.8 out of 10, Exceptional, (74)
"This was our first stay in Kihei and we had a wonderful time! The location was great and we appreciated the quietness of our space. We were able to walk to a nearby shopping plaza where we found delicious food and coffee. Our host was kind and communicated promptly and efficiently. We will be back! "
United States
Paige O.
The price is NZ$967
includes taxes & fees
11 Jan - 12 Jan
Oceanfront penthouse with amazing views at Kauhale Makai

Beautiful 1 bedroom ocean front condo with a/c in Menehune Shores ,Kihei

Beautiful 1 bedroom ocean front condo with a/c in Menehune Shores ,Kihei
North Kihei
8.6 out of 10, Excellent, (142)
"Location and property are great! It’s exactly as you’d want on your Maui vacation!"
United States
Caelle M.
The price is NZ$708
includes taxes & fees
20 Jan - 21 Jan
Beautiful 1 bedroom ocean front condo with a/c in Menehune Shores ,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, (267)
"Great stay"
United States
Noah C.
The price is NZ$679
includes taxes & fees
9 Jan - 10 Jan
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

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, (31)
"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$867
includes taxes & fees
16 Jan - 17 Jan
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Hana Town Center
9.6 out of 10, Exceptional, (111)
"Everything Good "
United States
Marc
The price is NZ$968
includes taxes & fees
14 Jan - 15 Jan
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Spacious & Remodeled Maui Vista 3213 Corner Unit!

Spacious & Remodeled Maui Vista 3213 Corner Unit!
South Kihei
9.6 out of 10, Exceptional, (138)
"Great place to stay. Cozy and cute and great location."
United States
Tad H.
The price is NZ$748
includes taxes & fees
4 Jan - 5 Jan
Spacious & Remodeled Maui Vista 3213 Corner Unit!

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hana
10.0 out of 10, Exceptional, (90)
"Very unique property near Hana. Great experience!"
United States
Keith R.
The price is NZ$978
includes taxes & fees
19 Jan - 20 Jan
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Tropical Paradise Awaits: Steps to Sugar Beach, Pool, Hot Tub & Free WiFi!

Tropical Paradise Awaits: Steps to Sugar Beach, Pool, Hot Tub & Free WiFi!
North Kihei
9.6 out of 10, Exceptional, (160)
"It was pretty much as described and met our needs.It was in a pretty good location for our requirements, and not too far from the port for our snorkelling trip."
United Kingdom
Carole W.
The price is NZ$943
includes taxes & fees
18 Jan - 19 Jan
Tropical Paradise Awaits: Steps to Sugar Beach, Pool, Hot Tub & Free WiFi!
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$486 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, 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 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.