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

Kailua Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

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$1,107
HK$2,490 total
includes taxes & fees
6 Aug - 7 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$2,446 total
includes taxes & fees
4 Aug - 5 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$2,712 total
includes taxes & fees
4 Aug - 5 Aug
Yonegan Maui Getaways - Haiku - Unit 4
1 bedroom, iron/ironing board, Internet, bed sheets

4. Yonegan Maui Getaways - Haiku - Unit 2

Yonegan Maui Getaways - Haiku - Unit 2
Haiku-Pauwela
9.0 out of 10, Wonderful, (15 reviews)
"The room is clean and the check-in instructions are pretty clear. The location is right off the route to Hana. The Google map did lead us to the wrong small side street; and since we are aware that possibility, we just U-turn back out and get back to the right street. We were there a bit there early and the room is not ready so we went to a near by sushi restaurant and had lunch. Perfect timing."
United States
Jack
The price is HK$1,121
HK$2,626 total
includes taxes & fees
6 Aug - 7 Aug
Yonegan Maui Getaways - Haiku - Unit 2
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, (523 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$1,647
HK$3,075 total
includes taxes & fees
16 Aug - 17 Aug
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Beach towels

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, (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$1,067
HK$3,311 total
includes taxes & fees
11 Aug - 12 Aug
Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC
Beach towels

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, (213 reviews)
"We had a great time! Everything was perfect. "
United States
Samantha S.
The price is HK$1,451
HK$3,496 total
includes taxes & fees
11 Aug - 12 Aug
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Exterior detail

8. Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.0 out of 10, Wonderful, (21 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$2,455 total
includes taxes & fees
23 Aug - 24 Aug
Yonegan Maui Getaways - Haiku - Unit 3
Smart TV, books

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, (16 reviews)
"We had a wonderful stay, our host was sweet"
United States
Nancy k.
The price is HK$1,532
HK$3,086 total
includes taxes & fees
7 Aug - 8 Aug
Eco-Friendly Condo on Road to Hāna - Walk to Beach
Beach nearby, sun-loungers, beach towels

10. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (63 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is HK$2,157
HK$4,479 total
includes taxes & fees
4 Aug - 5 Aug
Hale Nihi - Paia, Maui
Property grounds

11. 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, (81 reviews)
"Great stay with Heleina and John! The property was spacious, very clean, and comfortable. Despite the terrible weather in Hawaii, they went above and beyond to accommodate us, even offering a complimentary extra night in case we got stuck. Truly thoughtful hosts. Would definitely stay again and I highly recommend! "
United States
Anna H.
The price is HK$11,257
HK$23,147 total
includes taxes & fees
24 Aug - 25 Aug
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Beach nearby

12. 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$4,086
HK$8,546 total
includes taxes & fees
9 Aug - 10 Aug
North Shore retreat w/ lanai & beach access
Coffee/tea maker, fridge, microwave, oven

13. Paia 2 Bedroom 2 Bathroom

Paia 2 Bedroom 2 Bathroom
Paia
9.2 out of 10, Wonderful, (14 reviews)
"The Condo was perfect for our stay! Two bedrooms and two bathrooms! Plenty of space and very clean and nicely furnished. The kitchen had everything we needed and more. The location was located in a great area. Our host was wonderful with tips and recommendations! We would definitely stay here again!"
United States
Sherri W.
The price is HK$3,764
HK$6,960 total
includes taxes & fees
18 Aug - 19 Aug
Paia 2 Bedroom 2 Bathroom
Free WiFi, bed sheets

14. 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$3,141 total
includes taxes & fees
4 Aug - 5 Aug
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
Beach towels

15. 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$1,529
HK$3,020 total
includes taxes & fees
16 Aug - 17 Aug
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Outdoor dining

16. 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, (279 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 HK$812
HK$3,132 total
includes taxes & fees
5 Aug - 6 Aug
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Property grounds

17. 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, (249 reviews)
"Beautiful place to stay!"
United States
Mary B.
The price is HK$2,333
HK$4,667 total
includes taxes & fees
10 Aug - 11 Aug
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Exterior

18. 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, (148 reviews)
"Beautiful location. Quiet and relaxing."
United States
Frank A.
The price is HK$1,863
HK$3,536 total
includes taxes & fees
22 Aug - 23 Aug
Oceanview Condo in Hana-Let the ocean lull you to sleep
A heated pool

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 HK$1,136
HK$3,667 total
includes taxes & fees
4 Aug - 5 Aug
SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.
Beach towels

20. 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, (450 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is HK$1,529
HK$3,201 total
includes taxes & fees
18 Aug - 19 Aug
Fisher's Hana Bay Hale, Across from Hana Bay
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kailua Hotel Reviews

Maui Coast Hotel

Maui Coast Hotel

10/10 Excellent
"Great service and nice room. Pool was great!"
Sebastian 1-night trip
Posted 1 hour ago
Maui Coast 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
  • Use the map to find apartments and other holiday homes in the Kailua neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Kailua while they last

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, 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 Garden of Eden Arboretum and Maui Garden Of Eden - Botanical Gardens & Arboretum.

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.