Kailua Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Kailua

Private Beachfront Rental
9.8 out of 10, Exceptional, (209)
"All was excellent and as expected. I was very familiar with the area and always wanted to come back and visit and share with my spouse after 12 years away!"
Private Beachfront Rental
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
9.0 out of 10, Wonderful, (123)
"Wonderful location. Steps to the beach to watch the morning sunrise. "
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
Aston Waikiki Sunset
4.0 star property
7.8 out of 10, Good, (2819)
"Everything from checkin to checkout was amazing 👌"
The price is AU$384
includes taxes & fees
17 Nov - 18 Nov
Aston Waikiki Sunset
Kuhio Banyan Club
2.0 star property
6.8 out of 10, (1719)
"Very quaint and affordable. Nicely stocked with kitchen supplies. I wasn't expecting so much of what this hotel offered so I was quite surprised. I thought it would be very noisy since it's located in a very busy setting in Waikiki so thanks to good soundproofing. All sorts of restaurants and shops in good walking distance. Totally recommend!"
The price is AU$268
includes taxes & fees
6 Nov - 7 Nov
Kuhio Banyan Club
Aqua Skyline at Island Colony
3.0 star property
7.2 out of 10, Good, (1943)
"It was budget friendly, the room look like it could use alittle vacuuming but good enough for a 1 night sleep"
The price is AU$274
includes taxes & fees
27 Nov - 28 Nov
Aqua Skyline at Island Colony
Aston at the Waikiki Banyan
3.0 star property
7.2 out of 10, Good, (2474)
"Each condo is different and after requesting a different room which was no problem we had a terrific room The staff was eager to please and very pleasant. I highly recommend "
The price is AU$343
includes taxes & fees
6 Nov - 7 Nov
Aston at the Waikiki Banyan
Aston Waikiki Beach Tower
4.0 star property
9.2 out of 10, Wonderful, (1695)
"Great, comfy rooms and the kitchen came I. Handy! Great if you have kids. Nice having the beach across the street."
The price is AU$1,119
includes taxes & fees
6 Nov - 7 Nov
Aston Waikiki Beach Tower
Regency on Beachwalk Waikiki by OUTRIGGER
3.5 star property
8.2 out of 10, Very good, (371)
"I have stayed here many times and I always enjoy this condo/hotel. The staff is WONDERFUL and always very responsive. The location couldn't be better. An ABC store is right next door, two restaurants (Japanese and Italian) right next door, and I can see Egg's and Things from my balcony (next street over). The Friday night fireworks can easily been seen from the balcony as well. "
The price is AU$1,187
includes taxes & fees
20 Nov - 21 Nov
Regency on Beachwalk Waikiki by OUTRIGGER
Castle Waikīkī Shore
3.0 star property
8.2 out of 10, Very good, (1152)
"Castle Waikiki Shores did not disappoint. Hotel was right on the beach. We choose a beach view and man the view was amazing. Room was clean and spacious. "
Castle Waikīkī Shore
Hilton Grand Vacations Club at Hilton Hawaiian Village
4.0 star property
8.4 out of 10, Very good, (743)
"Absolutely fabulous suites with amazing views and so well appointed and equipped could not fault a thing! Hilton Grand Vacations Kalia Tower -Amazing "
Hilton Grand Vacations Club at Hilton Hawaiian Village
Royal Kuhio
3.5 star property
8.6 out of 10, Excellent, (406)
"Read the literature provided ahead of time. Our check in process was somewhat bumpy. Security was NOT helpful for clearly lost and confused tourists who just wanted to drop off bags and figure out where to park! After the rough start, this was a great place to stay. Easy walking distance to tons of fun activities. Comfortable and clean ... but for me, the parking situation made this THE place to stay. Have stayed other places in the same area that did not have designated parking and it...
The price is AU$392
includes taxes & fees
11 Nov - 12 Nov
Royal Kuhio
Waikiki Shore by OUTRIGGER
3.0 star property
8.2 out of 10, Very good, (426)
"The room was very comfortable and the staff very friendly. However, I was extremely disappointed that my request for an early check-in due, to my flight time, sent weeks and repeated days in advance, was met with empty promises. My wife and I had to wait 5 hrs until the standard checkin of 3pm even though the room was vacated in advance of 11am. Repeated visits to reception to request to expedite the room preparation was met with smiles but no action and an evident lack of communication within...
Waikiki Shore by OUTRIGGER
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
9.6 out of 10, Exceptional, (124)
"Great location for Waikiki - on the bus route from the airport, a few minutes walk from the nearedt beach, grrat for the shopping streets. Well equipped studio. Clean and tidy. Good yo have a laundry on site too. Beach chairs provided were helpful. Unfortunately the area is very expensive so you don't get a lot of space for ypur money, and buying groceries to cook is very costly. "
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
Spacious & Sophisticated Palms Studio Condo by RedAwning
3.0 star property
6.0 out of 10, (1)
Spacious & Sophisticated Palms Studio Condo by RedAwning
Espacio The Jewel Of Waikiki
5.0 star property
9.6 out of 10, Exceptional, (17)
"Super luxurious and amazing staff very clean and Super professional luxury feel"
The price is AU$7,167
includes taxes & fees
1 Dec - 2 Dec
Espacio The Jewel Of Waikiki
Ala Moana Condo by Zelloo
3.5 star property
6.4 out of 10, (38)
"Great accomodation for our hawaii trip!"
The price is AU$550
includes taxes & fees
18 Nov - 19 Nov
Ala Moana Condo by Zelloo
Clean studio in the heart of Waikiki!!
8.6 out of 10, Excellent, (22)
"Great spot for the price, perfect walking distance to pretty much everything. A ton of food trucks right across the street and just around the corner from some really cheap (for hawaii) bars. Will definitely be staying here again."
Clean studio in the heart of Waikiki!!
Tropical Studios at Marine Surf Waikiki
3.0 star property
8.2 out of 10, Very good, (316)
"This place was great! Every last detail is effectively communicated! For the value it’s amazing!!! Don’t let the other reviews fool you! You can’t beat the location and free parking!! I will stay there again!!"
The price is AU$404
includes taxes & fees
19 Nov - 20 Nov
Tropical Studios at Marine Surf Waikiki
Ocean view in Waikiki, Free Parking stall. Hawaiian dream vacation Free Wifi &AC
9.0 out of 10, Wonderful, (31)
"I travel to oahu every year for business and spend 8 to 12 weeks here every year. I have stayed at almost every hotel over the years and this is my new favorite place. Check in is easy, the owner is very accommodating and rrespinds quickly"
The price is AU$600
includes taxes & fees
12 Nov - 13 Nov
Ocean view in Waikiki, Free Parking stall. Hawaiian dream vacation Free Wifi &AC
Private Waikiki Condos with Corp Rental Car Discount and free Tour Guide App
3.0 star property
6.0 out of 10, (2)
"Not good with communication. The condo people had issues with reservation."
Private Waikiki Condos with Corp Rental Car Discount and free Tour Guide App
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.
Don't see what you're looking for?
See all available properties in Kailua
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Kailua you may be interested in

Hilton Hawaiian Village Waikiki Beach Resort
4.5 star property
8.0 out of 10, Very good, (7666)
"Great place."
The price is AU$460
includes taxes & fees
20 Nov - 21 Nov
Hilton Hawaiian Village Waikiki Beach Resort
'Alohilani Resort Waikiki Beach
5.0 star property
8.4 out of 10, Very good, (2348)
"Everything looks amazing. Love this place "
The price is AU$576
includes taxes & fees
6 Nov - 7 Nov
'Alohilani Resort Waikiki Beach
Waikiki Beach Marriott Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2853)
"Beautiful property, close to everything and lots of dining options. "
The price is AU$514
includes taxes & fees
24 Nov - 25 Nov
Waikiki Beach Marriott Resort & Spa
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.

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 a BBQ 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.

How many holiday rentals are there in Kailua?

With 167 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 Walk 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.