Kailua Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Kailua

Luxurious five-bedroom modern retreat

10.0 out of 10, Exceptional, (1)
"Great porperty that’s managed excellently, had a wonderful time and place was beautiful!"
The price is NZ$3,671
includes taxes & fees
1 Oct - 2 Oct
Luxurious five-bedroom modern retreat

Aston Waikiki Sunset

4.0 star property
7.8 out of 10, Good, (2995)
"We had a nice trip "
The price is NZ$316
includes taxes & fees
14 Oct - 15 Oct
Aston Waikiki Sunset

Aston at the Waikiki Banyan

3.0 star property
7.2 out of 10, Good, (2650)
"Location, friendly staff, kitchen "
The price is NZ$340
includes taxes & fees
12 Oct - 13 Oct
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 NZ$1,289
includes taxes & fees
17 Oct - 18 Oct
Aston Waikiki Beach Tower

Skyline Island Colony Hotel

3.0 star property
7.2 out of 10, Good, (2070)
"Nice stay "
The price is NZ$223
includes taxes & fees
29 Sept - 30 Sept
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 NZ$5,577
includes taxes & fees
21 Oct - 22 Oct
Espacio The Jewel Of Waikiki

Royal Kuhio

3.5 star property
8.6 out of 10, Excellent, (508)
"Clean room and easy parking"
The price is NZ$348
includes taxes & fees
29 Sept - 30 Sept
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 NZ$338
includes taxes & fees
2 Oct - 3 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, (535)
"Great location and amazing views. Clean and quiet. Bonus was the Steak Shack on ground level!"
Waikiki Shore by OUTRIGGER

Panoramic Oceanview Resort

4.0 star property
The price is NZ$783
includes taxes & fees
1 Oct - 2 Oct
Panoramic Oceanview Resort

Hawaiian Sun Holidays

3.0 star property
8.4 out of 10, Very good, (151)
"This was a wonderful place to stay. A bit older and could use some renovations however, the parking was free and it was so close to the beach. We felt safe and comfortable. "
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 NZ$775
includes taxes & fees
1 Oct - 2 Oct
Ocean View 1BR at Ilikai Marina

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 NZ$621
includes taxes & fees
2 Oct - 3 Oct
ALA MOANA

High Floor Ocean View Condo (King Bed and Parking)

3.5 star property
9.4 out of 10, Exceptional, (37)
"This was a great property and the location was perfect for a family of 4 to get around and to the beach. I would highly recommend this location if you are staying in Waikiki."
The price is NZ$737
includes taxes & fees
4 Oct - 5 Oct
High Floor Ocean View Condo (King Bed and Parking)

Partial Ocean View Condo with King or Queen Bed and Parking

3.5 star property
9.4 out of 10, Exceptional, (25)
"We had a great time at this property."
The price is NZ$708
includes taxes & fees
7 Oct - 8 Oct
Partial Ocean View Condo with King or Queen Bed and Parking

Tropical Studios at Marine Surf Waikiki

3.0 star property
8.4 out of 10, Very good, (359)
"Loved it. Close to everything that you could possibly need. Nothing fancy, but clean and the location can’t be beat. We would definitely stay here again. "
The price is NZ$431
includes taxes & fees
7 Oct - 8 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 NZ$578
includes taxes & fees
13 Oct - 14 Oct
Ilikai Marina Vacations

Luana Waikiki by Tropical Escapes Realty

2.5 star property
8.0 out of 10, Very good, (49)
"Close to the stores and beach. Quiet "
Luana Waikiki by Tropical Escapes Realty
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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 NZ$223 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

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 Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more! and Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa..

How many holiday rentals are there in Kailua?

With 160 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.