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, (37 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is €274
includes taxes & fees
8 Sept - 9 Sept
Yonegan Maui Getaways - Haiku

2. 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 €298
includes taxes & fees
1 Sept - 2 Sept
Yonegan Maui Getaways - Haiku - Unit 2

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 €308
includes taxes & fees
6 Sept - 7 Sept
Yonegan Maui Getaways - Haiku - Unit 4

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, (525 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 €347
includes taxes & fees
5 Sept - 6 Sept
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

5. 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 €277
includes taxes & fees
10 Sept - 11 Sept
Yonegan Maui Getaways - Haiku - Unit 6

6. 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 €277
includes taxes & fees
8 Sept - 9 Sept
Yonegan Maui Getaways - Haiku - Unit 3

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, (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 €379
includes taxes & fees
15 Sept - 16 Sept
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

8. 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 €399
includes taxes & fees
8 Sept - 9 Sept
Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.

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

10. 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 €461
includes taxes & fees
1 Sept - 2 Sept
Hale Nihi - Paia, Maui

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, (82 reviews)
"Absolutely incredible, the property and the host exceeded all expectations! "
Canada
Marley L.
The price is €2,544
includes taxes & fees
9 Sept - 10 Sept
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

12. 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 €855
includes taxes & fees
4 Sept - 5 Sept
North Shore retreat w/ lanai & beach access

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, (463 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is €340
includes taxes & fees
14 Sept - 15 Sept
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

14. 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, (250 reviews)
"Beautiful place to stay!"
United States
Mary B.
The price is €517
includes taxes & fees
2 Sept - 3 Sept
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

15. 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 €387
includes taxes & fees
2 Sept - 3 Sept
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

16. Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm
Kaʻeleku
9.4 out of 10, Exceptional, (310 reviews)
"We had a great 2 night stay here! The cottage is so peaceful and secluded, it was very cool to stay in the jungle. Was well stocked with everything we needed! "
United States
Kristina B.
The price is €488
includes taxes & fees
6 Sept - 7 Sept
Secluded cottage on Tropical flower farm

17. 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 €355
includes taxes & fees
1 Sept - 2 Sept
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

18. 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 €409
includes taxes & fees
1 Sept - 2 Sept
SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.

19. 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.
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

20. Beautiful Home in paradise!

Beautiful Home in paradise!
Kaʻeleku
9.6 out of 10, Exceptional, (178 reviews)
"Loved everything about it. As advertised. Will do it again."
United States
Monafou M.
The price is €579
includes taxes & fees
14 Sept - 15 Sept
Beautiful Home in paradise!
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 €274 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 Hosmer Grove.

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.