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

Kailua Holiday Rentals

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Our top choices for Kailua holiday rentals

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (37 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is AU$416
includes taxes & fees
15 Sept - 16 Sept
Yonegan Maui Getaways - Haiku

2. Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
9.0 out of 10, Wonderful, (22 reviews)
"Great location for driving the Road to Hana."
United States
Lisa
The price is AU$474
includes taxes & fees
14 Sept - 15 Sept
Yonegan Maui Getaways - Haiku - Unit 4

3. Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (42 reviews)
"Everything was great."
United States
Bryan
The price is AU$431
includes taxes & fees
10 Sept - 11 Sept
Yonegan Maui Getaways - Haiku - Unit 6

4. Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Hana
10.0 out of 10, Exceptional, (526 reviews)
"Absolutely wonderful place in paradise. Hosts were amazing. Brough us fresh eggs and fruit. Amazing view and love the kitty too!"
United States
Diann
The price is AU$534
includes taxes & fees
22 Sept - 23 Sept
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

5. 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, (217 reviews)
"Great location for our last night. Walk to the beach and close enough to the airport for an early flight."
United States
jeff s.
The price is AU$592
includes taxes & fees
15 Sept - 16 Sept
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

6. Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.

Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.
Paia
9.6 out of 10, Exceptional, (58 reviews)
"This was an amazing place to stay! So close to the beach and downtown Paia - we would totally recommend this place to any of our friends! "
United States
Lizzie B.
The price is AU$650
includes taxes & fees
11 Sept - 12 Sept
Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.

7. Eco-Friendly Condo on Road to Hāna - Walk to Beach

Eco-Friendly Condo on Road to Hāna - Walk to Beach
Paia
10.0 out of 10, Exceptional, (18 reviews)
"We had a wonderful stay, our host was sweet"
United States
Nancy k.
The price is AU$539
includes taxes & fees
10 Sept - 11 Sept
Eco-Friendly Condo on Road to Hāna - Walk to Beach

8. Yonegan Maui Getaways - Haiku - Unit 2

Yonegan Maui Getaways - Haiku - Unit 2
Haiku-Pauwela
9.0 out of 10, Wonderful, (15 reviews)
"This place is in a great location, less than 10 minutes from downtown Paia, with nice beaches nearby as well.We didn’t end up using the kitchen, but having a refrigerator and freezer was very convenient.The bed was soft and comfortable, and the pillows were great too.For this specific unit, the toilet does work properly you just need to make sure the handle is positioned correctly so the tank refills.Overall, this was a great rental and we enjoyed our stay."
United States
Raechell F.
The price is AU$455
includes taxes & fees
21 Sept - 22 Sept
Yonegan Maui Getaways - Haiku - Unit 2

9. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (65 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is AU$752
includes taxes & fees
15 Sept - 16 Sept
Hale Nihi - Paia, Maui

10. Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.0 out of 10, Wonderful, (22 reviews)
"Perfect getaway for an island vacation if your not planning on staying in just your room. Made breakfast every morning close to beaches, turtles and shops"
United States
Jeremiah J.
The price is AU$425
includes taxes & fees
17 Sept - 18 Sept
Yonegan Maui Getaways - Haiku - Unit 3

11. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
3.0 star property
Haiku
The price is AU$1,523
includes taxes & fees
16 Sept - 17 Sept
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

12. 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, (201 reviews)
"Comfortable, clean, well equipped cottage in the heart of Hana. Great place, highly recommend! "
United States
Michelle S.
The price is AU$630
includes taxes & fees
9 Sept - 10 Sept
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

13. 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, (464 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is AU$533
includes taxes & fees
11 Sept - 12 Sept
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

14. Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.4 out of 10, Exceptional, (461 reviews)
"We loved staying here, and it was great for a family of 4. Kitchen very well stocked and lots of room, ping pong table a plus. Great to be able to split up Road to Hana drive."
United States
Jason C.
The price is AU$556
includes taxes & fees
10 Sept - 11 Sept
Fisher's Hana Bay Hale, Across from Hana Bay

15. North Shore retreat w/ lanai & beach access

North Shore retreat w/ lanai & beach access
Paia
9.8 out of 10, Exceptional, (44 reviews)
"Great property in a great location. Great finishes and all the items stocked well."
United States
Jared W.
The price is AU$1,485
includes taxes & fees
21 Sept - 22 Sept
North Shore retreat w/ lanai & beach access

16. 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, (161 reviews)
"This was the perfect home base for a 3-night stay in Hana! The property is exceptionally clean, comfortable, quiet, and scenic. The property manager was also incredibly responsive to all of our questions both before and during our stay. We would absolutely stay here again!"
United States
Kelly Z.
The price is AU$783
includes taxes & fees
9 Sept - 10 Sept
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

17. 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, (12 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 AU$545
includes taxes & fees
10 Sept - 11 Sept
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

18. Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Central Kihei
9.6 out of 10, Exceptional, (81 reviews)
"We loved our stay! Great location"
United States
Madison
The price is AU$474
includes taxes & fees
10 Sept - 11 Sept
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

19. SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.

SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.
North Kihei
9.4 out of 10, Exceptional, (78 reviews)
"Excellent ground floor condo with easy access to the pool and beach. Clean, cozy, and comfortable with everything we needed including a washer and dryer, lots of beach chairs and beach towels and really nice staff. The grounds at the resort are beautiful and we loved the hot dry sauna and the jacuzzi! We will definitely stay here again!"
United States
Jodelle F.
The price is AU$635
includes taxes & fees
9 Sept - 10 Sept
SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.

20. 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, (151 reviews)
"Our stay was for one night and the condo was clean, well equipped, and the ocean waves lulled us to sleep. If doing the road to Hana an overnight stay here is recommended "
United States
Jaime C.
The price is AU$614
includes taxes & fees
9 Sept - 10 Sept
Oceanview Condo in Hana-Let the ocean lull you to sleep
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 favourite 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 depend 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 AU$416 per night. Entering your travel dates in the search wizard might find you 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 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.