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 NZ$502
includes taxes & fees
25 Aug - 26 Aug
Yonegan Maui Getaways - Haiku

2. Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (40 reviews)
"Everything was great."
United States
Bryan
The price is NZ$510
includes taxes & fees
13 Sept - 14 Sept
Yonegan Maui Getaways - Haiku - Unit 6

3. 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 NZ$577
includes taxes & fees
25 Aug - 26 Aug
Yonegan Maui Getaways - Haiku - Unit 4

4. 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, (57 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 NZ$735
includes taxes & fees
25 Aug - 26 Aug
Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.

5. 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, (524 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 NZ$642
includes taxes & fees
25 Aug - 26 Aug
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

6. 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, (215 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 NZ$742
includes taxes & fees
30 Aug - 31 Aug
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

7. 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 NZ$510
includes taxes & fees
25 Aug - 26 Aug
Yonegan Maui Getaways - Haiku - Unit 3

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 NZ$546
includes taxes & fees
26 Aug - 27 Aug
Yonegan Maui Getaways - Haiku - Unit 2

9. 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 NZ$653
includes taxes & fees
28 Aug - 29 Aug
Eco-Friendly Condo on Road to Hāna - Walk to Beach

10. 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, (110 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$823
includes taxes & fees
4 Sept - 5 Sept
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

11. 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, (463 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is NZ$630
includes taxes & fees
31 Aug - 1 Sept
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

12. 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, (456 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is NZ$676
includes taxes & fees
6 Sept - 7 Sept
Fisher's Hana Bay Hale, Across from Hana Bay

13. 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, (315 reviews)
"Kevin was a great host! Communication was prompt and he gave wonderful suggestions on places to eat, things to do.The condo was beautiful, very cozy and clean.We would definitely stay here again"
United States
Janet M.
The price is NZ$665
includes taxes & fees
11 Sept - 12 Sept
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

14. 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
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

15. 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 NZ$663
includes taxes & fees
26 Aug - 27 Aug
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

16. Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
North Kihei
10.0 out of 10, Exceptional, (44 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
The price is NZ$805
includes taxes & fees
4 Sept - 5 Sept
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

17. 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, (150 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 NZ$719
includes taxes & fees
6 Sept - 7 Sept
Oceanview Condo in Hana-Let the ocean lull you to sleep

18. 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
9.8 out of 10, Exceptional, (306 reviews)
"Awesome stay, all you need around there, very quiet place, good neighbors, excellent Host and amazing commons area."
United States
pablo
The price is NZ$645
includes taxes & fees
9 Sept - 10 Sept
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

19. Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit

Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit
Hana Town Center
9.6 out of 10, Exceptional, (64 reviews)
"Nice location "
United States
janie h.
The price is NZ$747
includes taxes & fees
19 Sept - 20 Sept
Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit

20. Tropical Kihei Resort, 3 Min Walk to Beach, A/C in All Rooms

Tropical Kihei Resort, 3 Min Walk to Beach, A/C in All Rooms
North Kihei
9.8 out of 10, Exceptional, (137 reviews)
"Positioned near the center of our travel area convenient to all needs and interests."
United States
Sharon W.
The price is NZ$1,012
includes taxes & fees
7 Sept - 8 Sept
Tropical Kihei Resort, 3 Min Walk to Beach, A/C in All Rooms
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$502 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 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.