Kailua Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Kailua vacation rentals

Vacation Home in Enchanted Lake

Luxurious five-bedroom modern retreat
8.6 out of 10, Excellent, (4 reviews)
"Great communication with host - property as advertised- we had a great stay"
United States
Wytske K.
The price is CA $1,299
CA $2,914 total
includes taxes & fees
Mar 1 - Mar 2
Luxurious five-bedroom modern retreat
9.6 out of 10, Exceptional, (111 reviews)
"House was clean. It was cool to stay in a farm setting. Location is a bit out of the way though, fair warning. Host was very responsive. They even had beach chairs and umbrellas to borrow which I appreciated. "
United States
Siddarth R.
The price is CA $180
CA $306 total
includes taxes & fees
Mar 1 - Mar 2
Create one of the most unique experiences on the beautiful Lā’ie country side.
4.0 star property
8.2 out of 10, Very good, (27 reviews)
"Great location and very clean condo"
United States
Rhonda
The price is CA $438
CA $886 total
includes taxes & fees
Mar 10 - Mar 11
Luxury Oceanview Punaluu Condo
9.4 out of 10, Exceptional, (102 reviews)
"Host did a good job welcoming us. Room was nice, bed was comfortable. Meet our need."
United States
Jeremy H.
The price is CA $115
CA $288 total
includes taxes & fees
Mar 13 - Mar 14
Waikiki renovated modern studio
10.0 out of 10, Exceptional, (107 reviews)
"Clean room and plenty of towels and shops nearby"
United States
Flavio
The price is CA $156
CA $463 total
includes taxes & fees
Mar 9 - Mar 10
Aloha Suite Near the Sea III - 2 Block Walk to Beach!
10.0 out of 10, Exceptional, (31 reviews)
"Great value with parking included! "
Canada
Rob T.
The price is CA $89
CA $409 total
includes taxes & fees
Mar 4 - Mar 5
Cozy condo at Hawaiian monarch- free parking, no resort fee, near beaches, shop
9.2 out of 10, Wonderful, (45 reviews)
"Everything was as promised. Ash was very responsive and helpful. I would stay here again."
United States
Bradley F.
The price is CA $112
CA $285 total
includes taxes & fees
Mar 4 - Mar 5
Renovated Specious Studio with Great View
9.8 out of 10, Exceptional, (18 reviews)
"Great place, location was great and nice and clean room. The chairs were perfect to bring to the beach as well and the hosts were easy to contact as well"
Canada
Anonymous traveller
The price is CA $122
CA $543 total
includes taxes & fees
Feb 28 - Mar 1
Beautiful Studio in the Heart of Vibrant Waikiki!
9.6 out of 10, Exceptional, (17 reviews)
"It's cozy and perfect for 2 people. There is food truck right across the street . The pool area is really nice with hot tub and bbq area. The beach is just 15 minute walk from this place. "
United States
Shraddha
The price is CA $130
CA $354 total
includes taxes & fees
Feb 28 - Mar 1
A Cozy and Romantic Studio at Heart of Waikiki
3.0 star property
9.6 out of 10, Exceptional, (11 reviews)
"The stay was amazing very lovely cozy place we enjoyed our stay , the only downfall can be the parking but we got lucky all days to be able to find free parking at walking distance."
United States
Margarita
The price is CA $142
CA $478 total
includes taxes & fees
Feb 28 - Mar 1
Cozy Studios at Aloha Surf Close to Waikiki Beach
9.0 out of 10, Wonderful, (26 reviews)
"Great sun rise view from my room. Enjoyed many meals out in the open air setting. Cental location for walkig around and exporloring the local area around. Had a fantastic time for my first trip there. Will defenitly return "
United States
Della
The price is CA $121
CA $534 total
includes taxes & fees
Feb 28 - Mar 1
**Diamond Head, Ocean, and Park Views**
9.4 out of 10, Exceptional, (128 reviews)
"Great location "
Canada
Terri Lynn C.
The price is CA $137
CA $363 total
includes taxes & fees
Mar 1 - Mar 2
❤️AWESOME STUDIOS❤️ 5min to 🏄‍♀️🏊‍♀️🏖🐠🐋🦈FREE 🚙🅿️ 250mbps+💻-FREE PARKING

Apartment in Waikiki

Ilikai Marina Vacations
3.0 star property
8.4 out of 10, Very good, (38 reviews)
"Clean rooms and spacious, small bathroom but amazing view "
United Kingdom
Neide Katila
The price is CA $172
CA $488 total
includes taxes & fees
Mar 18 - Mar 19
Ilikai Marina Vacations
10.0 out of 10, Exceptional, (42 reviews)
"Perfect stay, perfectly clean, bed was comfortable. Centrally located, food trucks were great and so was the restaurant downstairs. Great stay with beautiful views! "
United States
Tammi K.
The price is CA $131
CA $408 total
includes taxes & fees
Mar 29 - Mar 30
King Bed/Renovated/Canal& Mountain View/Walk Beach
9.8 out of 10, Exceptional, (25 reviews)
"Wonderful property. "
United States
Chris T.
The price is CA $134
CA $357 total
includes taxes & fees
Mar 30 - Mar 31
Charming cozy condo in marvelous Honolulu with WiFi

Aparthotel in Diamond Head - Kapahulu - St. Louis

@ Marbella Lane -coastal Retreat Near Diamond Head
2.5 star property
The price is CA $553
CA $897 total
includes taxes & fees
Mar 23 - Mar 24
@ Marbella Lane -coastal Retreat Near Diamond Head
8.6 out of 10, Excellent, (67 reviews)
"This was perfect for us! Close enough to walk to the beach, restaurants and stores. Very clean! And when I had a question, they were very responsive!"
United States
Hayley F.
The price is CA $144
CA $571 total
includes taxes & fees
Mar 2 - Mar 3
Lovely apartment with ocean views - near beach
9.8 out of 10, Exceptional, (191 reviews)
"Very close to the beach, clean house, shops nearby, I stayed for 1 week and everything was great. "
Italy
Emanuela D.
The price is CA $143
CA $444 total
includes taxes & fees
Mar 30 - Mar 31
Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!

Aparthotel in Waikiki

Skyline Island Colony Hotel
3.0 star property
7.2 out of 10, Good, (2,184 reviews)
"Average hotel, great location. "
United States
Carolina
The price is CA $162
CA $232 total
includes taxes & fees
Mar 2 - Mar 3
Skyline Island Colony Hotel
9.6 out of 10, Exceptional, (30 reviews)
"everything was great, I'm sure I'll come to this hotel again"
United States
Nazar
The price is CA $214
CA $602 total
includes taxes & fees
Mar 25 - Mar 26
Partial Ocean View Condo with King or Queen Bed and Parking
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Kailua Hotel Reviews

Find out more about Kailua

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?

BEST LOCATION , LANIKAI registration number W00530010-01 TMK 43005029 Licensed!: This Kailua vacation home rental is located in the mountains and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of books. Other favorite homes for rent in Kailua are BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY and Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!.

How many vacation rentals are there in Kailua?

With 148 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 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.