Kailua Holiday Rentals

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Our top choices for Kailua holiday rentals

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (31 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is AU$455
includes taxes & fees
16 June - 17 June
Yonegan Maui Getaways - Haiku

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, (28 reviews)
"This place was perfect. Enjoyed 2 days of big surf and stormy weather from the lanai. A true vacation. My favorite place to stay on Maui. Hana town is da best. "
United States
Kimo B.
The price is AU$689
includes taxes & fees
4 June - 5 June
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.4 out of 10, Exceptional, (36 reviews)
"Everything was set up to be an amazing experience and we would definitely stay again."
Canada
Tamara
The price is AU$799
includes taxes & fees
5 June - 6 June
Kihei Ali'i Kai Condos with Free Parking

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Hana Town Center
9.6 out of 10, Exceptional, (118 reviews)
"Beautiful place to stay in Hana and super nice people. "
United States
Tanya L.
The price is AU$712
includes taxes & fees
5 June - 6 June
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Beautiful Home in paradise!

Beautiful Home in paradise!
Kaʻeleku
9.6 out of 10, Exceptional, (174 reviews)
"Stay was great. House was very comfortable"
United States
Pam I.
Beautiful Home in paradise!

OCEANFRONT RESORT - LAST MINUTE Savings! Kihei Sands Beachfront Condos - B5

OCEANFRONT RESORT - LAST MINUTE Savings! Kihei Sands Beachfront Condos - B5
North Kihei
9.6 out of 10, Exceptional, (86 reviews)
"Great hosts and beach! Sorry my grandkids were a little noisy but they loved it! "
United States
John C.
The price is AU$982
includes taxes & fees
4 June - 5 June
OCEANFRONT RESORT - LAST MINUTE Savings! Kihei Sands Beachfront Condos - B5

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, (79 reviews)
"Great view, excellent location. 2 -3 nights is the perfect amount of time in Hana."
United States
Jim
The price is AU$705
includes taxes & fees
5 June - 6 June
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm
Kaʻeleku
9.4 out of 10, Exceptional, (301 reviews)
"Beautiful secluded property. Great instuctions provided by the host. The cottage had everything we needed for our stay. "
United States
Lokahi
The price is AU$771
includes taxes & fees
30 June - 1 July
Secluded cottage on Tropical flower farm

OCEANFRONT CONDO - Kihei Sands Beachfront Condos-B8

OCEANFRONT CONDO - Kihei Sands Beachfront Condos-B8
North Kihei
9.8 out of 10, Exceptional, (111 reviews)
"Rating Details: The property manager was more than helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Condo is as described and photographed, directly over the pool and with great views of the ocean and beach. The area is a bit of a drive from restaurants and shops, but centrally located for access to all parts of the island. The...
United States
Pamela W.
The price is AU$1,121
includes taxes & fees
4 June - 5 June
OCEANFRONT CONDO - Kihei Sands Beachfront Condos-B8

OCEANFRONT RESORT - COME FOR WHALE SEASON! Kihei Sands Beachfront Condo - B12

OCEANFRONT RESORT - COME FOR WHALE SEASON! Kihei Sands Beachfront Condo - B12
North Kihei
9.4 out of 10, Exceptional, (75 reviews)
"Advised that this property was perfect for the family and they really enjoyed the location and property"
United States
Michele W.
The price is AU$964
includes taxes & fees
4 June - 5 June
OCEANFRONT RESORT - COME FOR WHALE SEASON! Kihei Sands Beachfront Condo - B12

Stay in Hana Upstairs

Stay in Hana Upstairs
Hana Town Center
9.6 out of 10, Exceptional, (43 reviews)
"Beautiful remote location! A little short on kitchen supplies like wine glasses and Tupperware. We loved the cabin feel of the place. Great access to the Hana Road and excellent nearby waterfall hikes!"
United States
Paulina B.
The price is AU$663
includes taxes & fees
4 June - 5 June
Stay in Hana Upstairs

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, (246 reviews)
"I appreciated everything as advertised. Would have preferred mini splits or AC in the bedrooms, but still a nice peaceful spot."
United States
Robert
The price is AU$806
includes taxes & fees
7 June - 8 June
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

OCEANFRONT RESORT-CHECK OUT OUR WINTER RATES! Kihei Sands Beachfrnt Condo B14

OCEANFRONT RESORT-CHECK OUT OUR WINTER RATES! Kihei Sands Beachfrnt Condo B14
North Kihei
9.8 out of 10, Exceptional, (105 reviews)
"Great spot and the property was fantastic!"
United States
Michael B.
The price is AU$926
includes taxes & fees
14 June - 15 June
OCEANFRONT RESORT-CHECK OUT OUR WINTER RATES! Kihei Sands Beachfrnt Condo B14

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (101 reviews)
"This place was amazing to stay! I wished that I had been booked ii for a longer stay. It was extremely clean and well kept. I look forward to staying there again on my return to Hana. Mahalo Shelly!"
United States
jef p.
The price is AU$753
includes taxes & fees
2 July - 3 July
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Great location between Hana Town and Hamoa Beach, private, family-friendly

Great location between Hana Town and Hamoa Beach, private, family-friendly
Hana Town Center
9.8 out of 10, Exceptional, (239 reviews)
"Great location in Hana. Cozy and private. "
United States
Heather F.
The price is AU$716
includes taxes & fees
6 June - 7 June
Great location between Hana Town and Hamoa Beach, private, family-friendly

OCEANFRONT RESORT- Winter Deals Awaits - Kihei Sands Beachfront Condos- B6

OCEANFRONT RESORT- Winter Deals Awaits - Kihei Sands Beachfront Condos- B6
North Kihei
9.6 out of 10, Exceptional, (79 reviews)
"We loved this condo! It was clean and had everything that we needed!! The free coffee by the pool every morning was amazing!! The location is perfect! Loved that the beach is just steps from our condo door! Will definitely stay again!! Mahalo!"
United States
Nicole M.
The price is AU$982
includes taxes & fees
4 June - 5 June
OCEANFRONT RESORT- Winter Deals Awaits - Kihei Sands Beachfront Condos- B6

Paia 2 Bedroom 2 Bathroom

Paia 2 Bedroom 2 Bathroom
Paia
9.2 out of 10, Wonderful, (12 reviews)
"The house was perfect for the 6 of us and near a beautiful cove. "
United States
Vanessa C.
The price is AU$750
includes taxes & fees
4 June - 5 June
Paia 2 Bedroom 2 Bathroom

Waiohuli Beach Hale Ocean View Condos with Parking

Waiohuli Beach Hale Ocean View Condos with Parking
3.0 star property
Central Kihei
9.8 out of 10, Exceptional, (6 reviews)
"Grounds were beautiful. Beach view and access great. Quality of condo was in need of refreshing. Some broken doors, and in need of repair. The condo was clean."
United States
Eric
The price is AU$1,182
includes taxes & fees
21 June - 22 June
Waiohuli Beach Hale Ocean View Condos with Parking

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens
Hana
10.0 out of 10, Exceptional, (512 reviews)
"Very welcoming helpful host. Everything was just as it should be! The property is beautifully and subtly landscaped with incredible beauty!"
United States
Harold E.
The price is AU$614
includes taxes & fees
8 June - 9 June
Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens

OCEANFRONT RESORT- WHALES+LOW WINTER RATES- Kihei Sands Beachfront Condo-B10

OCEANFRONT RESORT- WHALES+LOW WINTER RATES- Kihei Sands Beachfront Condo-B10
North Kihei
9.6 out of 10, Exceptional, (104 reviews)
"Room was great, loved the beach access! View from the balcony was nice too!"
United States
Linda W.
The price is AU$1,020
includes taxes & fees
4 June - 5 June
OCEANFRONT RESORT- WHALES+LOW WINTER RATES- Kihei Sands Beachfront Condo-B10
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 favourite 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 depend 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 AU$455 per night. Entering your travel dates in the search wizard might find you 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 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.