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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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 25 - May 26
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, (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
Interior entrance
Aston at the Waikiki Banyan
3.0 star property
7.2 out of 10, Good, (2384)
"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 CA $232
CA $325 total
includes taxes & fees
May 22 - May 23
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, (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 19 - May 20
Royal Kuhio
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 $776
CA $987 total
includes taxes & fees
May 19 - May 20
Aston Waikiki Beach Tower
Exterior
Castle Waikīkī Shores
3.0 star property
8.2 out of 10, Very good, (1104)
"I loved the property. The views were wonderful. Everything was neat and clean. The only complaint is the shower was way to cold and the dryer wasn't venting. Had to hang my clothes all over the room to dry them before my flight. All in all the place is terrific!"
Castle Waikīkī Shores
Exterior
Hilton Grand Vacations Club at Hilton Hawaiian Village
4.0 star property
8.6 out of 10, Excellent, (691)
"We had an amazing time. We will book again in the future"
The price is CA $461
CA $608 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 $166
CA $357 total
includes taxes & fees
May 18 - May 19
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 21 - May 22
Aqua Skyline at Island Colony
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.
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
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
5.8 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 $101
CA $423 total
includes taxes & fees
May 19 - May 20
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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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, (6480)
"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
Fireplace
'Alohilani Resort Waikiki Beach
5.0 star property
8.2 out of 10, Very good, (2099)
"The front entrance and the coffee shop inside on the first floor."
The price is CA $469
CA $643 total
includes taxes & fees
Jun 2 - Jun 3
'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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kailua. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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