Kailua Holiday Rentals

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Holiday Rentals in Kailua

Aston Waikiki Sunset

4.0 star property
7.8 out of 10, Good, (3001)
"This hotel was clean, close to the beach, easy parking and felt the aloha spirit "
The price is AU$277
includes taxes & fees
31 Oct - 1 Nov
Aston Waikiki Sunset

Aston at the Waikiki Banyan

3.0 star property
7.2 out of 10, Good, (2653)
"Location, friendly staff, kitchen "
The price is AU$271
includes taxes & fees
2 Nov - 3 Nov
Aston at the Waikiki Banyan

Aston Waikiki Beach Tower

4.0 star property
9.2 out of 10, Wonderful, (1782)
"Beautiful beach front property. Great location, walkable to many restaurants and shops. We stayed here twice Sep. 2024 & 2025 We’ll definitely be back!"
The price is AU$2,052
includes taxes & fees
23 Oct - 24 Oct
Aston Waikiki Beach Tower

Skyline Island Colony Hotel

3.0 star property
7.2 out of 10, Good, (2073)
"Nice stay "
The price is AU$222
includes taxes & fees
5 Oct - 6 Oct
Skyline Island Colony Hotel

Castle Waikīkī Shore

3.0 star property
8.2 out of 10, Very good, (1215)
"Nice and quiet, love the view."
Castle Waikīkī Shore

Espacio The Jewel Of Waikiki

5.0 star property
9.6 out of 10, Exceptional, (19)
"The hotel was great, the staff were amazing, and the view from the balcony was beautiful."
The price is AU$5,144
includes taxes & fees
6 Oct - 7 Oct
Espacio The Jewel Of Waikiki

Royal Kuhio

3.5 star property
8.6 out of 10, Excellent, (511)
"Clean room and easy parking"
The price is AU$285
includes taxes & fees
28 Oct - 29 Oct
Royal Kuhio

Bishop Suites At The Executive Centre

4.0 star property
7.6 out of 10, Good, (64)
"Absolutely loved my stay! The only thing I was thrown off about was an extra fifty eight dollar charge when checking in and a separate deposit charge of two hundred and fifty. Currently still awaiting my money back on that."
The price is AU$295
includes taxes & fees
13 Oct - 14 Oct
Bishop Suites At The Executive Centre

Regency on Beachwalk Waikiki by OUTRIGGER

3.5 star property
8.2 out of 10, Very good, (427)
"Staff is very friendly and the location is convenient. Plenty of room for a family of 4."
Regency on Beachwalk Waikiki by OUTRIGGER

Waikiki Shore by OUTRIGGER

3.0 star property
8.4 out of 10, Very good, (537)
"Great location and amazing views. Clean and quiet. Bonus was the Steak Shack on ground level!"
The price is AU$2,759
includes taxes & fees
3 Nov - 4 Nov
Waikiki Shore by OUTRIGGER

Panoramic Oceanview Resort

4.0 star property
The price is AU$891
includes taxes & fees
22 Oct - 23 Oct
Panoramic Oceanview Resort

Hawaiian Sun Holidays

3.0 star property
8.4 out of 10, Very good, (153)
"Enjoyed my stay in this spacious condo. Although a little dated, the condo was clean, had a great view, comfy bed, and great water pressure in the shower. Staff was friendly and accommodating. Free parking was a big plus and no issues with finding an available stall. I definitely recommend and look forward to staying here again."
Hawaiian Sun Holidays

Ocean View 1BR at Ilikai Marina

3.0 star property
10.0 out of 10, Exceptional, (6)
"Great location for family with kids."
The price is AU$754
includes taxes & fees
16 Oct - 17 Oct
Ocean View 1BR at Ilikai Marina

Partial Ocean View Condo with King or Queen Bed and Parking

3.5 star property
9.6 out of 10, Exceptional, (24)
"We had a great time at this property."
The price is AU$619
includes taxes & fees
7 Oct - 8 Oct
Partial Ocean View Condo with King or Queen Bed and Parking

ALA MOANA

3.5 star property
5.0 out of 10, (2)
"Refused to clean room, made them pay to add bags in room aw"
The price is AU$558
includes taxes & fees
13 Oct - 14 Oct
ALA MOANA

High Floor Ocean View Condo (King Bed and Parking)

3.5 star property
9.4 out of 10, Exceptional, (38)
"It was the perfect place to stay especially for the price!"
The price is AU$644
includes taxes & fees
6 Oct - 7 Oct
High Floor Ocean View Condo (King Bed and Parking)

Tropical Studios at Marine Surf Waikiki

3.0 star property
8.4 out of 10, Very good, (362)
"Everything was great! Mahalo!"
The price is AU$377
includes taxes & fees
14 Oct - 15 Oct
Tropical Studios at Marine Surf Waikiki

Ilikai Marina Vacations

3.0 star property
8.2 out of 10, Very good, (22)
"Very clean, well equipped and lots of mirrors "
The price is AU$505
includes taxes & fees
13 Oct - 14 Oct
Ilikai Marina Vacations

Luana Waikiki by Tropical Escapes Realty

2.5 star property
8.2 out of 10, Very good, (50)
"Close to the stores and beach. Quiet "
Luana Waikiki by Tropical Escapes Realty

Diamond Head and Ocean views with King Bed and Parking

3.5 star property
9.8 out of 10, Exceptional, (10)
"Great location."
The price is AU$724
includes taxes & fees
16 Oct - 17 Oct
Diamond Head and Ocean views with King Bed and Parking
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

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$222 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

Are there holiday rentals 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. Nature enthusiasts will enjoy the popular beaches in Kailua.

What are some of the best holiday rentals that Kailua has to offer?

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY: This highly rated holiday home rental in Kailua is located on the beach, and has a balcony, a private garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Other favourite homes for rent in Kailua are Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa. and Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!.

How many holiday rentals are there in Kailua?

With 162 Expedia holiday rentals, you're guaranteed to find just the right place for your Kailua stay.

What’s there to see and do in Kailua?

Kalama Beach Park and Kailua Bay Beach are a couple of lovely local spots to get outside and enjoy nature. You’ll find favourite places to visit such as Ala Moana Center and Waikiki Beach in the wider area.

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 feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.