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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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Kailua holiday rentals

Terrace/patio

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (36 reviews)
"Large room and bathroom. Nice little kitchen area. We had a room with two balconies so great air flow through to cool the room. Beautiful area of Hawaii to explore"
Canada
Amanda
The price is HK$992
HK$2,355 total
includes taxes & fees
23 Aug - 24 Aug
Yonegan Maui Getaways - Haiku
Exterior

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 HK$966
HK$2,464 total
includes taxes & fees
16 Aug - 17 Aug
Yonegan Maui Getaways - Haiku - Unit 6
Exterior

3. Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
9.0 out of 10, Wonderful, (21 reviews)
"Great location for driving the Road to Hana."
United States
Lisa
The price is HK$1,199
HK$2,738 total
includes taxes & fees
19 Aug - 20 Aug
Yonegan Maui Getaways - Haiku - Unit 4
Beach towels

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 HK$1,091
HK$3,349 total
includes taxes & fees
18 Aug - 19 Aug
Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC
Property grounds

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 HK$1,648
HK$3,093 total
includes taxes & fees
16 Aug - 17 Aug
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Beach towels

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)
"We had a great time! Everything was perfect. "
United States
Samantha S.
The price is HK$1,451
HK$3,514 total
includes taxes & fees
19 Aug - 20 Aug
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Smart TV, books

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 HK$1,469
HK$3,012 total
includes taxes & fees
18 Aug - 19 Aug
Eco-Friendly Condo on Road to Hāna - Walk to Beach
1 bedroom, iron/ironing board, Internet, bed sheets

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 HK$1,122
HK$2,644 total
includes taxes & fees
13 Aug - 14 Aug
Yonegan Maui Getaways - Haiku - Unit 2
Exterior detail

9. 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 HK$966
HK$2,464 total
includes taxes & fees
24 Aug - 25 Aug
Yonegan Maui Getaways - Haiku - Unit 3
Beach towels

10. 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, (460 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is HK$1,530
HK$3,029 total
includes taxes & fees
31 Aug - 1 Sept
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Outdoor dining

11. 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, (305 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 HK$812
HK$3,134 total
includes taxes & fees
13 Aug - 14 Aug
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Beach nearby, sun-loungers, beach towels

12. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (64 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is HK$2,157
HK$4,514 total
includes taxes & fees
21 Aug - 22 Aug
Hale Nihi - Paia, Maui
Free WiFi, bed sheets

13. Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
North Kihei
9.2 out of 10, Wonderful, (11 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 HK$863
HK$3,142 total
includes taxes & fees
21 Aug - 22 Aug
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
Interior

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
The price is HK$3,530
HK$8,622 total
includes taxes & fees
31 Aug - 1 Sept
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
Exterior

15. 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 HK$1,765
HK$3,413 total
includes taxes & fees
24 Aug - 25 Aug
Oceanview Condo in Hana-Let the ocean lull you to sleep
Beach towels

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, (454 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is HK$1,530
HK$3,185 total
includes taxes & fees
24 Aug - 25 Aug
Fisher's Hana Bay Hale, Across from Hana Bay
A heated pool

17. 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 HK$1,194
HK$3,745 total
includes taxes & fees
24 Aug - 25 Aug
SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.
Property grounds

18. Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (82 reviews)
"Great view, excellent location. 2 -3 nights is the perfect amount of time in Hana."
United States
Jim
The price is HK$2,165
HK$3,157 total
includes taxes & fees
12 Aug - 13 Aug
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Property grounds

19. Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Hana Town Center
9.6 out of 10, Exceptional, (30 reviews)
"Loved the view. Property was beautiful. Great place for a couple of quiet nights in Hana."
United States
Vera G.
The price is HK$2,134
HK$3,111 total
includes taxes & fees
13 Aug - 14 Aug
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Beach nearby

20. North Shore retreat w/ lanai & beach access

North Shore retreat w/ lanai & beach access
Paia
9.8 out of 10, Exceptional, (44 reviews)
"Absolutely perfect accommodations! It was very well equipped, perfectly clean & a fantastic location. One thing I would note is that it is on the second floor and there isn’t an elevator so you need to be able to carry your luggage. But other than that, I would highly recommend this condo."
United States
Kristin J.
The price is HK$4,088
HK$8,590 total
includes taxes & fees
19 Aug - 20 Aug
North Shore retreat w/ lanai & beach access
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

Maui Beach Hotel

Maui Beach Hotel

10/10 Excellent
"Clean room, friendly staff and amenities are family friendly. My family and I had a great time!"
Caroline 2-night trip
Posted 13 hours ago
Maui Beach Hotel

Find out more about Kailua

Search for holiday rentals in Kailua on Expedia! You can easily find your home rentals, villas, holiday apartments in Kailua using one of the methods below:

  • View our selection of featured holiday rentals in Kailua
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Look no further and take a look at our great range of rental properties in Kailua!

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.