Holiday Rentals in Kailua

    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

Next weekend
In two weeks

Holiday Rentals in Kailua

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

9.2 out of 10, Wonderful, (137)
"Our family enjoyed our stay at this lovely home. The location was perfect and the beach was fantastic. So nice to spend some time relaxing here. "
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

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 €2,454
includes taxes & fees
29 Jul - 30 Jul
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, (199)
"Our stay was wonderful. The location was perfect. Nice amenities and kitchen/bathrooms had xtra supplies needed for our stay. Truly a gem in Kailua. Easy access to the beach and stores. The owners were easy to connnect with and a cute folder with instructions and recommendations were provided. We will be back. Thank you "
Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!

Aston at the Waikiki Banyan

3.0 star property
7.2 out of 10, Good, (2612)
"Location was perfect for us. Great view from our room."
The price is €152
includes taxes & fees
27 Aug - 28 Aug
Aston at the Waikiki Banyan

Skyline Island Colony Hotel

3.0 star property
7.2 out of 10, Good, (2028)
"The check-in staff were amazingly helpful and friendly and very easy to work with."
The price is €129
includes taxes & fees
29 Jul - 30 Jul
Skyline Island Colony Hotel

Aston Waikiki Sunset

4.0 star property
7.8 out of 10, Good, (2955)
"Excellent front desk staff. "
The price is €170
includes taxes & fees
10 Aug - 11 Aug
Aston Waikiki Sunset

Aston Waikiki Beach Tower

4.0 star property
9.2 out of 10, Wonderful, (1763)
"There was construction but the property was in a great location. Staff was also very polite and welcoming "
The price is €518
includes taxes & fees
19 Aug - 20 Aug
Aston Waikiki Beach Tower

Bishop Suites At The Executive Centre

4.0 star property
7.6 out of 10, Good, (57)
"Good staff and great room"
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 €3,516
includes taxes & fees
30 Jul - 31 Jul
Espacio The Jewel Of Waikiki

Castle Waikīkī Shore

3.0 star property
8.2 out of 10, Very good, (1188)
"Our stay was great. Located right on Beach."
Castle Waikīkī Shore

Luana Waikiki by Tropical Escapes Realty

2.5 star property
8.0 out of 10, Very good, (38)
"The staff was so friendly. My friend and I rented bikes and they let us store our bikes in our hotel room. Loved our stay!"
The price is €305
includes taxes & fees
3 Aug - 4 Aug
Luana Waikiki by Tropical Escapes Realty

Royal Kuhio

3.5 star property
8.6 out of 10, Excellent, (486)
"Good location walking distance to shopping beach and restaurant and free parking. Enjoyed are stay there."
The price is €242
includes taxes & fees
24 Aug - 25 Aug
Royal Kuhio

Regency on Beachwalk Waikiki by OUTRIGGER

3.5 star property
8.2 out of 10, Very good, (416)
"Staff are very nice"
Regency on Beachwalk Waikiki by OUTRIGGER

Hawaiian Sun Holidays

3.0 star property
8.4 out of 10, Very good, (144)
"Second time coming back here because we enjoyed this place so much! Communication with the rental manager was easy and fast. And while some of the furniture looks a little out dated, it’s always clean and furnished perfectly. "
Hawaiian Sun Holidays

Waikiki Shore by OUTRIGGER

3.0 star property
8.2 out of 10, Very good, (522)
"Loved this property for what we wanted but could use some updating. Loved it had washer and dryer and that the place provides the soap. Beds were comfy and lovely views "
Waikiki Shore by OUTRIGGER

Ocean View Condo with King or Queen Bed and Parking

3.5 star property
9.6 out of 10, Exceptional, (19)
"We had a great time at this property."
The price is €329
includes taxes & fees
29 Jul - 30 Jul
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, (9)
"Great stay ! My family and I loved it …"
The price is €380
includes taxes & fees
5 Aug - 6 Aug
Diamond Head and Ocean views with King Bed and Parking

High Floor Ocean View Condo (King Bed and Parking)

3.0 star property
9.2 out of 10, Wonderful, (30)
"It was the perfect place to stay especially for the price!"
The price is €334
includes taxes & fees
29 Jul - 30 Jul
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 €372
includes taxes & fees
9 Aug - 10 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 €396
includes taxes & fees
2 Aug - 3 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?

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 Luxurious five-bedroom modern retreat.

How many holiday rentals are there in Kailua?

With 161 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.