Kailua Holiday Rentals

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Holiday Rentals in Kailua

Pool
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!
On the beach, beach towels
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
9.2 out of 10, Wonderful, (113)
"Family from New England visiting my family who lives in the north shore of Oahu. Perfect location."
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
Suite, 2 Bedrooms, Ocean View
Aston Waikiki Sunset
4.0 star property
7.8 out of 10, Good, (2718)
"Location is great. Building itself is old but it’s very typical in Waikiki area. Elevators sometimes will need some waiting time. "
The price is AU$303
per night
11 May - 12 May
Aston Waikiki Sunset
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Lobby sitting area
Kuhio Banyan Club
2.0 star property
6.8 out of 10, (1667)
"This place was amazing "
The price is AU$217
per night
13 May - 14 May
Kuhio Banyan Club
Condo, 1 Bedroom, City View (Unit 55 ,1Bath) | Terrace/patio
Regency on Beachwalk Waikiki by OUTRIGGER
3.5 star property
8.0 out of 10, Very good, (335)
"The staff was extremely friendly and amenable to our request for any help. We got a two bedroom suite, but it only had one bathroom (I didn’t pay close enough attention); but it all worked out for our party."
The price is AU$923
per night
25 May - 26 May
Regency on Beachwalk Waikiki by OUTRIGGER
Interior entrance
Aston at the Waikiki Banyan
3.0 star property
7.2 out of 10, Good, (2378)
"The customer service was very good. The people at front desk are helpful, nice, and really good people. The property needs up dating and so do the rooms, but views so beautiful from our room."
The price is AU$334
per night
27 May - 28 May
Aston at the Waikiki Banyan
Studio, Ocean View (Unit #1305)
Waikiki Shore by OUTRIGGER
3.0 star property
8.0 out of 10, Very good, (369)
"Waikiki Shore is great, great location, great view from balcony, easy, clean. We will be back. "
Waikiki Shore by OUTRIGGER
Beach nearby
Royal Kuhio
3.5 star property
8.6 out of 10, Excellent, (320)
"This property is condos - not a hotel. When we arrived, we could not find a check-in desk. After we mentioned Expedia, the security guard directed us to VI Resorts which was a office off the main entrance. "
The price is AU$410
per night
14 May - 15 May
Royal Kuhio
View from property
Aston Waikiki Beach Tower
4.0 star property
9.2 out of 10, Wonderful, (1634)
"The front desk is so great!!!!"
The price is AU$1,068
per night
19 May - 20 May
Aston Waikiki Beach Tower
Deluxe Suite, 2 Bedrooms, Beach View | Private kitchen
CASTLE Waikīkī Shore
3.0 star property
8.2 out of 10, Very good, (1101)
"Castle Waikiki Shores was absolutely the best!! Our room was Amazing, breathtaking views, right on the beach, walking distance from EVERYTHING. Husband had an amazing 50th birthday! Very clean, great staff and was the hotel very very peaceful!! We enjoyed the Friday night fireworks right from our balcony, with love, laughter and cocktails!! I'm telling everyone I know, this is the best best place to stay!!! Thank you Castle Waikiki Shores!! "
CASTLE Waikīkī Shore
Front of property - evening/night
Hilton Grand Vacations Club at Hilton Hawaiian Village
4.0 star property
8.6 out of 10, Excellent, (689)
"Our main requirement was to have a one bedroom and a kitchen, The Hilton Hawaiian village met these requirements. Safety and easy beach access was another positive as well. Certain towers definitely need an update, their age is showing. The biggest negative is that if you're stsying at their "Grand Vacations" rooms, then their "timeshare" sales people will hound you into a presentation. Unfortunately, I took the time to view their pitch and it wasn't pleasant at all. They don't want you to ask...
The price is AU$604
per night
7 June - 8 June
Hilton Grand Vacations Club at Hilton Hawaiian Village
Beach nearby, white sand, sun-loungers, beach umbrellas
Tropical Studios at Marine Surf Waikiki
3.0 star property
8.2 out of 10, Very good, (291)
"Good location "
The price is AU$359
per night
12 May - 13 May
Tropical Studios at Marine Surf Waikiki
Exterior
Aqua Skyline at Island Colony
3.0 star property
7.2 out of 10, Good, (1912)
"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$248
per night
21 May - 22 May
Aqua Skyline at Island Colony
Exterior
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
9.6 out of 10, Exceptional, (108)
"Mike’s place was perfect! Clean, comfortable, and well appointed. He had starters for coffee, hair dryer, a beach chair and cooler and even an umbrella. Location is great - quick walk to beach, restaurants, shopping. Pool and surrounding deck was clean and very nice. Great host- I hope to stay again during my next visit to Honolulu. Mahalo Mike."
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
Outdoor pool
Espacio The Jewel Of Waikiki
5.0 star property
9.8 out of 10, Exceptional, (14)
"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$3,028
per night
20 May - 21 May
Espacio The Jewel Of Waikiki
Pool
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!!
Reception
Ala Moana Condo by Orgoto
3.5 star property
5.6 out of 10, (17)
"The room is right next to the elevator shaft, so if you’re a light sleeper this will keep you up all night. The room has no extra toiletries and because it’s a privately owned condo inside of the main hotel the hotel housekeeping will not service the room in anyway, which also means there is no daily cleaning. The property manager messaged frequently enough but never communicated that there wayany additional resort costs. The booking says that resort costs are not included but at no point were...
The price is AU$372
per night
13 May - 14 May
Ala Moana Condo by Orgoto
Studio | Pool
Spacious & Sophisticated Palms Studio Condo by RedAwning
3.0 star property
Spacious & Sophisticated Palms Studio Condo by RedAwning
Beach
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
Exterior
King Bed Suite at The Waikiki Grand - Just steps away from Waikiki Beach
8.6 out of 10, Excellent, (18)
"This room was nice, and located near the beach, zoo, park, and aquarium. I had a blast and was away from the room most of the time. I slept great and the sun deck is great during sunrise. Thank You!"
King Bed Suite at The Waikiki Grand - Just steps away from Waikiki Beach
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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

Pool
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!
View from room
Hilton Hawaiian Village Waikiki Beach Resort
4.0 star property
8.2 out of 10, Very good, (6447)
"I liked being on a resort"
The price is AU$468
per night
16 May - 17 May
Hilton Hawaiian Village Waikiki Beach Resort
Fireplace
'Alohilani Resort Waikiki Beach
5.0 star property
8.2 out of 10, Very good, (2096)
"This hotel was gorgeous and the entire staff was extremely accommodating. The lobby was a highlight for us and my boyfriend enjoyed how well equipped the gym was. Drinks were great as well--would absolutely visit again!"
The price is AU$553
per night
14 May - 15 May
'Alohilani Resort Waikiki Beach
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$217 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 183 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?

Kailua Bay Beach and Kailua 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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