Kailua Vacation Rentals

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Vacation 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, (2719)
"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 CA $285
CA $393 total
includes taxes & fees
Jun 17 - Jun 18
Aston Waikiki Sunset
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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, (336)
"Was a decent place to stay close to downtown. Parking quite limited/tight spaces and an extra fee on top of stay :(. Also no swimming pool or hot tub on-site, though they did offer to let you use the other outrigger’s pool. Staff friendly and helpful in helping orient you, provide directions etc. kitchen was equipped to do meals vs. eating out."
The price is CA $246
CA $849 total
includes taxes & fees
Jun 15 - Jun 16
Regency on Beachwalk Waikiki by OUTRIGGER
Lobby sitting area
Kuhio Banyan Club
2.0 star property
6.8 out of 10, (1667)
"This place was amazing "
The price is CA $155
CA $239 total
includes taxes & fees
May 20 - May 21
Kuhio Banyan Club
Interior entrance
Aston at the Waikiki Banyan
3.0 star property
7.2 out of 10, Good, (2385)
"I love this hotel! great location "
The price is CA $231
CA $324 total
includes taxes & fees
May 21 - May 22
Aston at the Waikiki Banyan
View from property
Aston Waikiki Beach Tower
4.0 star property
9.2 out of 10, Wonderful, (1636)
"The front desk is so great!!!!"
The price is CA $775
CA $987 total
includes taxes & fees
May 19 - May 20
Aston Waikiki Beach Tower
Studio, Ocean View (Unit #1305)
Waikiki Shore by OUTRIGGER
3.0 star property
8.0 out of 10, Very good, (371)
"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, (330)
"I liked pretty much the whole experience of staying at this property."
The price is CA $313
CA $369 total
includes taxes & fees
May 20 - May 21
Royal Kuhio
Exterior
Castle Waikīkī Shores
3.0 star property
8.2 out of 10, Very good, (1104)
"I loved the location, the property was very nice. However, the person who checked us in gave us all the information but, seemed very bored."
Castle Waikīkī Shores
Exterior
Hilton Grand Vacations Club at Hilton Hawaiian Village
4.0 star property
8.6 out of 10, Excellent, (692)
"We had an amazing time. We will book again in the future"
The price is CA $461
CA $609 total
includes taxes & fees
Jun 7 - Jun 8
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 CA $159
CA $348 total
includes taxes & fees
Jun 2 - Jun 3
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 CA $169
CA $240 total
includes taxes & fees
May 19 - May 20
Aqua Skyline at Island Colony
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 CA $2,724
CA $3,213 total
includes taxes & fees
Jun 4 - Jun 5
Espacio The Jewel Of Waikiki
Property grounds
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.
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!!
Studio | Pool
Spacious & Sophisticated Palms Studio Condo by RedAwning
3.0 star property
Spacious & Sophisticated Palms Studio Condo by RedAwning
Reception
Ala Moana Condo by Orgoto
3.5 star property
5.8 out of 10, (19)
"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 CA $148
CA $478 total
includes taxes & fees
May 19 - May 20
Ala Moana Condo by Orgoto
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
Property grounds
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
Don't see what you're looking for?
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

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, (6483)
"We loved our room in the Tapa Tower. It was really clean and it seemed recently updated. We had a great 180 degree view of from the balcony spanning from the ocean to the mountains. The room itself was very quiet except for a screaming baby next door who quieted down after awhile, but when you're in Waikiki it's not reasonable to expect total quiet. We'd love to return here and stay longer. Mia, who checked us in, was fantastic. Super friendly."
The price is CA $358
CA $503 total
includes taxes & fees
May 20 - May 21
Hilton Hawaiian Village Waikiki Beach Resort
Suite, 2 Bedrooms, Non Smoking, Oceanfront | View from room
Sheraton Waikiki Beach Resort
4.0 star property
9.0 out of 10, Wonderful, (1874)
"We love the place. We thought they could give us a better room given we stay there all the time… Also, the adult pool was super hard to get a seat… not fun to spend your vacation trying to reserve a seat… but I get it… it is so nice! "
The price is CA $550
CA $706 total
includes taxes & fees
May 29 - May 30
Sheraton Waikiki Beach Resort
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kailua vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kailua vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kailua vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kailua vacation rentals we have selected for you start as low as CA $148 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kailua rentals

At Expedia, we put the best Kailua vacation 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 vacation.

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 vacation rentals in Kailua?

Yes, we offer vacation rentals near the most popular sights in Kailua, or you can select a more secluded option if you want a relaxing place to stay. Nature enthusiasts will enjoy the popular beaches in Kailua.

What are some of the best vacation home rentals in Kailua?

Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!: This Kailua vacation home rental is located near the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the spa 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 vacation rentals are there in Kailua?

With 181 Expedia vacation rentals, you're sure 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 favorite places to visit like Ala Moana Center and Waikiki Beach Walk in the larger area.

What’s a vacation rental in Kailua like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Kailua. Vacation rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.

Recent reviews of Kailua properties
Expedia verified reviews

Wayfinder Waikiki

Wayfinder Waikiki

5/5 Excellent
"I liked the property, The rooms are small but everything else is excellent. Very welcoming and they have beach stuff that you can use at no cost. Easy to get around and there’s an ABC store right down the street that you can do quick runs for anything."
A verified traveller stayed at Wayfinder Waikiki
Posted 1 day ago
Wayfinder Waikiki