Kailua Holiday Rentals

    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

Our top choices for Kailua holiday rentals

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 AU$3,310
includes taxes & fees
1 Sept - 2 Sept
Luxurious five-bedroom modern retreat

Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!

9.6 out of 10, Exceptional, (202)
"The location is unbeatable: short walk to the best beach! Beds are comfortable. We probably missed the description that the second bathroom is downstairs, outside the unit, but it wasn't a big issue for us. We had a great stay."
Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

9.2 out of 10, Wonderful, (140)
"This is a wonderful place for a family vacation (in my case, three generations). Very well stocked. Steps to a beautiful beach with very few people on it. Paradise!"
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

Aston Waikiki Sunset

4.0 star property
7.8 out of 10, Good, (2972)
"Every thing was great "
The price is AU$308
includes taxes & fees
18 Sept - 19 Sept
Aston Waikiki Sunset

Skyline Island Colony Hotel

3.0 star property
7.2 out of 10, Good, (2045)
"The hotel provided comfortable beds and great services! We enjoyed our stays. Thank you!"
The price is AU$250
includes taxes & fees
7 Sept - 8 Sept
Skyline Island Colony Hotel

Aston at the Waikiki Banyan

3.0 star property
7.2 out of 10, Good, (2622)
"Absolutely loved how close it is to the beach "
The price is AU$302
includes taxes & fees
9 Sept - 10 Sept
Aston at the Waikiki Banyan

Aston Waikiki Beach Tower

4.0 star property
9.2 out of 10, Wonderful, (1773)
"Location of the hotel was perfect "
The price is AU$974
includes taxes & fees
17 Sept - 18 Sept
Aston Waikiki Beach Tower

Bishop Suites At The Executive Centre

4.0 star property
7.6 out of 10, Good, (58)
"Large living room!"
The price is AU$285
includes taxes & fees
24 Aug - 25 Aug
Bishop Suites At The Executive Centre

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$6,295
includes taxes & fees
20 Aug - 21 Aug
Espacio The Jewel Of Waikiki

Luana Waikiki by Tropical Escapes Realty

2.5 star property
8.0 out of 10, Very good, (44)
"Great property for families! Clean, quiet, perfect location for everything!!!"
Luana Waikiki by Tropical Escapes Realty

Castle Waikīkī Shore

3.0 star property
8.2 out of 10, Very good, (1194)
"Excellent location and friendly staff. Right on the beach."
Castle Waikīkī Shore

Hawaiian Sun Holidays

3.0 star property
8.4 out of 10, Very good, (147)
"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

Regency on Beachwalk Waikiki by OUTRIGGER

3.5 star property
8.2 out of 10, Very good, (419)
"We had an enjoyable stay. The beds were comfortable, room and facility was clean. Staff were very friendly and pleasant. Beaches was a short walk and we were able to find many food options nearby. We would stay here again! "
Regency on Beachwalk Waikiki by OUTRIGGER

Royal Kuhio

3.5 star property
8.6 out of 10, Excellent, (491)
"Good location walking distance to shopping beach and restaurant and free parking. Enjoyed are stay there."
The price is AU$416
includes taxes & fees
17 Sept - 18 Sept
Royal Kuhio

Waikiki Shore by OUTRIGGER

3.0 star property
8.4 out of 10, Very good, (530)
"Great location and amazing views. Clean and quiet. Bonus was the Steak Shack on ground level!"
The price is AU$3,991
includes taxes & fees
19 Sept - 20 Sept
Waikiki Shore by OUTRIGGER

Partial Ocean View Condo with King or Queen Bed and Parking

3.5 star property
9.0 out of 10, Wonderful, (22)
"We had a great time at this property."
The price is AU$679
includes taxes & fees
20 Aug - 21 Aug
Partial Ocean View Condo with King or Queen Bed and Parking

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$757
includes taxes & fees
23 Aug - 24 Aug
Diamond Head and Ocean views with King Bed and Parking

High Floor Ocean View Condo (King Bed and Parking)

3.5 star property
9.4 out of 10, Exceptional, (33)
"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 AU$660
includes taxes & fees
22 Aug - 23 Aug
High Floor Ocean View Condo (King Bed and Parking)

Waikiki Sunset Close to Beach with Parking

3.0 star property
8.4 out of 10, Very good, (11)
"Good location "
The price is AU$683
includes taxes & fees
27 Aug - 28 Aug
Waikiki Sunset Close to Beach with Parking

Ocean View 1BR at Ilikai Marina

3.0 star property
10.0 out of 10, Exceptional, (3)
"This condo was very well renovated and was extremely clean. The view was amazing!"
The price is AU$774
includes taxes & fees
20 Aug - 21 Aug
Ocean View 1BR at Ilikai Marina
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

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?

Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!: This highly rated holiday home rental in Kailua offers an outdoor pool, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind. Other favourite homes for rent in Kailua are Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa. and BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY.

How many holiday rentals are there in Kailua?

With 166 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.