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

Holiday Rentals in Kailua

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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, (39 reviews)
"Rooms were very comfortable and clean. Super easy check in and out. Great location, not touristy at all, which is what I like for a vacation! Great staff made everything super easygoing. Will definitely be back!"
United States
Jennifer
The price is €284
includes taxes & fees
20 Oct - 21 Oct
Yonegan Maui Getaways - Haiku

2. Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.2 out of 10, Wonderful, (24 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 €285
includes taxes & fees
29 Oct - 30 Oct
Yonegan Maui Getaways - Haiku - Unit 3

3. Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
9.0 out of 10, Wonderful, (23 reviews)
"Check in instructions was bit complicated property but we were able to figure out in sometime was clean and nice AC was working fine keep house cool, Hot tub was the MVP of the stay loved and enjoyed overall stay highly recommend for future potential travelers place was quite and very close to nature perfect spot to start road to hana adventure!"
United States
NIDHI
The price is €312
includes taxes & fees
18 Oct - 19 Oct
Yonegan Maui Getaways - Haiku - Unit 4

4. 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 €289
includes taxes & fees
20 Oct - 21 Oct
Yonegan Maui Getaways - Haiku - Unit 6

5. 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 €303
includes taxes & fees
15 Nov - 16 Nov
Yonegan Maui Getaways - Haiku - Unit 2

6. Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi

Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi
Paia
9.8 out of 10, Exceptional, (99 reviews)
"Close walk to a beach. Owner took care of maintenance problem quickly."
United States
David
The price is €384
includes taxes & fees
18 Oct - 19 Oct
Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi

7. 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, (224 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 €404
includes taxes & fees
16 Oct - 17 Oct
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

8. Condo w/ Lanai at Beginning of Road to Hana!

Condo w/ Lanai at Beginning of Road to Hana!
Paia
9.2 out of 10, Wonderful, (45 reviews)
"The property was very clean and well-appointed. It was a great location that allowed us to walk in to Mama's Fish House. The host was extremely helpful and proactive and checked to make sure we had everything we needed. If you are looking for a place to stay in Paia, this is it."
United States
Martin S.
The price is €378
includes taxes & fees
18 Oct - 19 Oct
Condo w/ Lanai at Beginning of Road to Hana!

9. 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, (535 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
The price is €361
includes taxes & fees
18 Oct - 19 Oct
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

10. Locally-Owned Eco-Friendly Condo on Road to Hana - Walk to Beach

Locally-Owned Eco-Friendly Condo on Road to Hana - Walk to Beach
Paia
10.0 out of 10, Exceptional, (21 reviews)
"Chloe was very helpful! Her place was very convenient for an early trip to go to Hana. The place was clean and furnished and had everything we needed. Clear instructions smooth check in&out. Chloe was also fast with responses when I had questions. Would recommend to stay here!"
United States
Janette
The price is €410
includes taxes & fees
29 Oct - 30 Oct
Locally-Owned Eco-Friendly Condo on Road to Hana - Walk to Beach

11. Maui's best Surf, wdsurf, snorkeling by secluded beach+ bdAC.

Maui's best Surf, wdsurf, snorkeling by secluded beach+ bdAC.
Paia
9.6 out of 10, Exceptional, (61 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 €466
includes taxes & fees
19 Oct - 20 Oct
Maui's best Surf, wdsurf, snorkeling by secluded beach+ bdAC.

12. 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 €428
includes taxes & fees
16 Oct - 17 Oct
Hale Nihi - Paia, Maui

13. North Shore retreat w/ lanai & beach access

North Shore retreat w/ lanai & beach access
Paia
9.8 out of 10, Exceptional, (44 reviews)
"Wonderful property."
United States
Samantha A.
The price is €856
includes taxes & fees
25 Oct - 26 Oct
North Shore retreat w/ lanai & beach access

14. Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Makawao
10.0 out of 10, Exceptional, (82 reviews)
"This place was perfect for our big group!"
United States
Lisa B.
The price is €2,898
includes taxes & fees
14 Nov - 15 Nov
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

15. Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (68 reviews)
"Everything was as described and very clean"
United States
Kathy
The price is €341
includes taxes & fees
14 Nov - 15 Nov
Stay in Hana #2

16. 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, (466 reviews)
"We had a very nice stay at this home."
United States
Jenn / Ant S.
The price is €397
includes taxes & fees
17 Oct - 18 Oct
Fisher's Hana Bay Hale, Across from Hana Bay

17. 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, (472 reviews)
"Super nice place and so helpful to have for a night at the end of the Road to Hana!"
United States
Tyler M.
The price is €397
includes taxes & fees
19 Oct - 20 Oct
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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, (308 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 €361
includes taxes & fees
28 Oct - 29 Oct
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

19. 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, (253 reviews)
"Beautiful place to stay!"
United States
Mary B.
The price is €542
includes taxes & fees
18 Oct - 19 Oct
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

20. 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, (280 reviews)
"Absolutely perfect stay! Kevin was very kind and very communicative. I highly recommend staying here when visiting Kīhei."
United States
Sylvia
The price is €362
includes taxes & fees
22 Oct - 23 Oct
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
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 €284 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 Maui Garden Of Eden - Botanical Gardens & Arboretum and Makawao Park.

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.