Kailua Holiday Rentals

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Holiday Rentals in Kailua

Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
10.0 out of 10, Exceptional, (3)
"My husband and I enjoyed six wonderful weeks in this house. From the moment we drove down that palm tree-lined road and stepped into the walled off courtyard, we knew we had picked the right place for our get-away. The house was tastefully and comfortably appointed. The kitchen, laundry room and bathrooms were all fully outfitted. We slept so well in the luxurious bedrooms, lulled by trade winds at night and waking to birds chirping in the morning. The outdoor lanai and backyard furniture made...
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
9.2 out of 10, Wonderful, (114)
"Great location."
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
Aston Waikiki Sunset
4.0 star property
7.8 out of 10, Good, (2721)
"Overall everything was great. I gave it a 4 because we paid for the week of parking and 3/5 days they oversold the parking so we had to park and pay at the zoo. Also bigger vehicles not a good idea as we couldn’t park one of our vehicles here at all due to height. We know for next time to get a smaller car too. But we paid for 5 days of parking and 3/5 days ended up paying somewhere else for parking. Property also didn’t fill our soaps and towels fully each time so we had to ask for...
The price is AU$322
per night
19 June - 20 June
Aston Waikiki Sunset
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Waikiki Shore by OUTRIGGER
3.0 star property
8.0 out of 10, Very good, (376)
"I was worried with some of the reviews I read so here’s my honest opinion. We’re a family of 6 (with older kids) staying for a week. It was very spacious, 2 full bathrooms and washer & dryer were a plus, loved the open kitchen and the beach view was the best! The beach was right there with easy access to it. We bought groceries and the fridge/freezer worked great. Appliances worked normal, there were pots & pans, most of what you’d expect in a kitchen. We cooked breakfast & lunches, bought out...
Waikiki Shore by OUTRIGGER
Regency on Beachwalk Waikiki by OUTRIGGER
3.5 star property
8.0 out of 10, Very good, (341)
"We really liked the private feel. It was like having our own private apartment less than a block from the beach and walking distance to so many shopping and food options. Five stars!!! ⭐️⭐️⭐️⭐️⭐️"
The price is AU$948
per night
30 June - 1 July
Regency on Beachwalk Waikiki by OUTRIGGER
Kuhio Banyan Club
2.0 star property
6.8 out of 10, (1675)
"This place was amazing "
The price is AU$231
per night
9 June - 10 June
Kuhio Banyan Club
Aston at the Waikiki Banyan
3.0 star property
7.2 out of 10, Good, (2403)
" The rooms were very spacious and very well laid out with a large kitchen and sitting area. There was a window A/C that i could properly regulate & the staff cleaned daily. We stayed 5 nights, the front desk staff were extremely nice especially Kelly who checked us in & her manager. Yes the furniture is dated but we were gone all day till the evening & it was so relaxing to come back to our nice room with a gorgeous view. The 1st time in Oahu we had stayed a block away at T.F. resort -very...
The price is AU$305
per night
20 June - 21 June
Aston at the Waikiki Banyan
Aston Waikiki Beach Tower
4.0 star property
9.2 out of 10, Wonderful, (1642)
"Very boutique service and the staff was extremely responsive. "
The price is AU$1,414
per night
25 June - 26 June
Aston Waikiki Beach Tower
Hilton Grand Vacations Club at Hilton Hawaiian Village
4.0 star property
8.6 out of 10, Excellent, (702)
"Beautiful view excellent service my family enjoyed "
The price is AU$608
per night
16 June - 17 June
Hilton Grand Vacations Club at Hilton Hawaiian Village
Royal Kuhio
3.5 star property
8.6 out of 10, Excellent, (335)
"We stayed at the Royal Kuhio for 10 days. Room was clean, kitchen was fully stocked with kitchen supplies. We were able to cook many meals in the kitchen and Beds were comfy. Staff were kind and helpful! They are located in the perfect location as well! Walking distance to wakiki beach, Royal Hawaiian center, international market, and many dining and shopping areas. We enjoyed our stay, and would come again! Mahalo! "
The price is AU$426
per night
10 June - 11 June
Royal Kuhio
Castle Waikīkī Shores
3.0 star property
8.2 out of 10, Very good, (1109)
"The weather was bad most of the time, but it was a great stay!"
Castle Waikīkī Shores
Espacio The Jewel Of Waikiki
5.0 star property
9.6 out of 10, Exceptional, (15)
"Beautiful property and condo like accommodations with the floor all to ourselves. Highest level concierge services I have experienced with transportation services to and from airport included in stay. Will definitely be back! "
The price is AU$3,467
per night
10 June - 11 June
Espacio The Jewel Of Waikiki
Aqua Skyline at Island Colony
3.0 star property
7.2 out of 10, Good, (1914)
"Rooms need to be updated. Drapes were extremely past due to be replaced. Can’t beat the view of the ocean, canal & Diamond Head. Pool area and laundry were great. "
The price is AU$267
per night
11 June - 12 June
Aqua Skyline at Island Colony
Spacious & Sophisticated Palms Studio Condo by RedAwning
3.0 star property
Spacious & Sophisticated Palms Studio Condo by RedAwning
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
9.6 out of 10, Exceptional, (109)
"We really enjoyed our visit to Hawaii and Michael’s property was perfect for us there was a strange smell from fridge which did linger on items we chilled so refrained from using but overall good and worked for us and our budget! Would stay again"
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
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, (295)
"Great place, close to everything waikiki has to offer. T Parking is a huge plus! the condo did have chairs, umbrella and boogie boards for use which was very convenient. "
The price is AU$378
per night
27 June - 28 June
Tropical Studios at Marine Surf Waikiki
Oceanside Estate - Spacious home with Pool & AC
10.0 out of 10, Exceptional, (1)
"We all enjoyed the property. It was a ways away from most activities but was quiet and we fit perfectly. The family all travel extensively and use B and B's and other means.. We did enjoy our stay and would recommend it."
Oceanside Estate - Spacious home with Pool & AC
Coconut Hideaway -Ocean across the street
6.4 out of 10, (5)
"Amazing. Absolutely amazing. Everything we needed was provided. Easy access to all amenities. Quiet and relaxing. Definitely would stay here again and again and again."
Coconut Hideaway -Ocean across the street
Private Waikiki Condos with Corp Rental Car Discount and free Tour Guide App
3.0 star property
The price is AU$672
per night
4 July - 5 July
Private Waikiki Condos with Corp Rental Car Discount and free Tour Guide App
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See all available properties in Kailua
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.

Other types of properties in Kailua you may be interested in

Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
10.0 out of 10, Exceptional, (3)
"My husband and I enjoyed six wonderful weeks in this house. From the moment we drove down that palm tree-lined road and stepped into the walled off courtyard, we knew we had picked the right place for our get-away. The house was tastefully and comfortably appointed. The kitchen, laundry room and bathrooms were all fully outfitted. We slept so well in the luxurious bedrooms, lulled by trade winds at night and waking to birds chirping in the morning. The outdoor lanai and backyard furniture made...
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
Hilton Hawaiian Village Waikiki Beach Resort
4.0 star property
8.2 out of 10, Very good, (6637)
"Hawaiian Village had a lot to choose from stores, food and the parking garage was very easy access from both sides of the resort. "
The price is AU$514
per night
16 June - 17 June
Hilton Hawaiian Village Waikiki Beach Resort
Hyatt Regency Waikiki Beach Resort & Spa
4.0 star property
8.6 out of 10, Excellent, (3351)
"Great location and the staff is amazing. The pool is a bit of a joke but with the beach just across the street there is no point of using it. Overall very happy with it. "
The price is AU$498
per night
8 July - 9 July
Hyatt Regency Waikiki Beach 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.

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$231 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?

Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!: This highly rated holiday home rental in Kailua is located near the beach, and has a balcony, a 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. Make the most of Access to hot tub in this rental home to help you unwind. Another good choice for your trip to Kailua is BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY.

How many holiday rentals are there in Kailua?

With 181 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.

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