Photo by Lisa A Schmidt

Kailua Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Kailua

Interior
Luxurious five-bedroom modern retreat

Luxurious five-bedroom modern retreat

Enchanted Lake
10.0 out of 10, Exceptional, (2)
"Great porperty that’s managed excellently, had a wonderful time and place was beautiful!"
United States
Bryan C.
The price is ￥148,352
￥331,037 total
includes taxes & fees
Nov 30 - Dec 1
Luxurious five-bedroom modern retreat
Property grounds
Create one of the most unique experiences on the beautiful Lā’ie country side.

Create one of the most unique experiences on the beautiful Lā’ie country side.

Laie
9.6 out of 10, Exceptional, (102)
"The host contacted us ahead of time and had great communication. She provided helpful instructions for finding the property and we enjoyed staying there. "
United States
Amy C.
The price is ￥17,146
￥36,288 total
includes taxes & fees
Dec 5 - Dec 6
Create one of the most unique experiences on the beautiful Lā’ie country side.
On the beach
Beach Front Condo w/ Beautiful Sunrises on Private Sandy Beach + Turtles + Perfect Snorkel Spot

Beach Front Condo w/ Beautiful Sunrises on Private Sandy Beach + Turtles + Perfect Snorkel Spot

2.5 star property
Hauula
10.0 out of 10, Exceptional, (12)
"Very clean unit. They thought of everything that you would need to make your stay fun."
United States
Mark S.
The price is ￥50,963
￥130,623 total
includes taxes & fees
Dec 26 - Dec 27
Beach Front Condo w/ Beautiful Sunrises on Private Sandy Beach + Turtles + Perfect Snorkel Spot
BBQ/picnic area
Skyline Island Colony Hotel

Skyline Island Colony Hotel

3.0 star property
Waikiki
7.2 out of 10, Good, (2122)
"Have stayed here a couple of times and always had a great experience "
Canada
Aida
The price is ￥14,108
￥21,249 total
includes taxes & fees
Dec 9 - Dec 10
Skyline Island Colony Hotel
Standard Room, 1 Bedroom | Living area | 32-inch LCD TV with cable channels, TV, DVD player
Aston at the Waikiki Banyan

Aston at the Waikiki Banyan

3.0 star property
Waikiki
7.2 out of 10, Good, (2672)
"Amazing check on smooth friendly amazing room and view will only stay here when I visit now! "
United States
John
The price is ￥21,768
￥31,573 total
includes taxes & fees
Dec 18 - Dec 19
Aston at the Waikiki Banyan
On the beach, white sand
High Floor Ocean View Condo (King Bed and Parking)

High Floor Ocean View Condo (King Bed and Parking)

3.5 star property
Waikiki
9.4 out of 10, Exceptional, (40)
"It was the perfect place to stay especially for the price!"
United States
Abigail
The price is ￥19,834
￥62,348 total
includes taxes & fees
Dec 5 - Dec 6
High Floor Ocean View Condo (King Bed and Parking)
Iron/ironing board, free WiFi
Island Colony hotel

Island Colony hotel

2.5 star property
Waikiki
The price is ￥20,613
￥46,053 total
includes taxes & fees
Nov 30 - Dec 1
Island Colony hotel
Suite, Ocean View | Beach/ocean view
Bishop Suites At The Executive Centre

Bishop Suites At The Executive Centre

4.0 star property
Downtown Honolulu
7.8 out of 10, Good, (66)
"Large living room!"
United States
Elika
The price is ￥21,794
￥30,346 total
includes taxes & fees
Dec 2 - Dec 3
Bishop Suites At The Executive Centre
Beach nearby, sun loungers, beach towels
Aloha Suite Near the Sea II, 3 Block Walk to Beach

Aloha Suite Near the Sea II, 3 Block Walk to Beach

Waikiki
9.6 out of 10, Exceptional, (136)
"The stay was phenomenal, next time we come hoping you’re available!!"
United States
Brian R.
The price is ￥9,218
￥40,930 total
includes taxes & fees
Dec 16 - Dec 17
Aloha Suite Near the Sea II, 3 Block Walk to Beach
1 bedroom, iron/ironing board, free WiFi, bed sheets
Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!

Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!

Waikiki
9.8 out of 10, Exceptional, (185)
"painless entry great location "
United States
Matthew M.
The price is ￥16,326
￥50,622 total
includes taxes & fees
Dec 4 - Dec 5
Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!
Building design
Ilikai Marina Vacations

Ilikai Marina Vacations

3.0 star property
Waikiki
8.4 out of 10, Very Good, (32)
"Clean and good use of space. "
United States
Cristina Katia Garcia
The price is ￥18,419
￥53,977 total
includes taxes & fees
Dec 3 - Dec 4
Ilikai Marina Vacations
Beach
Cozy condo at Hawaiian monarch- free parking, no resort fee, near beaches, shop

Cozy condo at Hawaiian monarch- free parking, no resort fee, near beaches, shop

Waikiki
9.8 out of 10, Exceptional, (29)
"Great value for the price. Excellent location. Especially loved the parking space — very convenient. Definitely the best choice."
Canada
Daffy
The price is ￥11,014
￥47,223 total
includes taxes & fees
Nov 28 - Nov 29
Cozy condo at Hawaiian monarch- free parking, no resort fee, near beaches, shop
Sun loungers, beach towels
Beautiful Studio in the Heart of Vibrant Waikiki!

Beautiful Studio in the Heart of Vibrant Waikiki!

Waikiki
9.8 out of 10, Exceptional, (18)
"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 traveler
The price is ￥12,298
￥59,294 total
includes taxes & fees
Dec 3 - Dec 4
Beautiful Studio in the Heart of Vibrant Waikiki!
Pool
Deluxe studio with kitchenette, furnished lanai, pool, & hot tub

Deluxe studio with kitchenette, furnished lanai, pool, & hot tub

Waikiki
8.8 out of 10, Excellent, (41)
"Centrally located. The room is a little dated, and could use some replenishing. But it was a comfortable stay. As the only time I spent in the room was for naps and sleeping."
United States
Dante A.
The price is ￥24,216
￥61,808 total
includes taxes & fees
Dec 19 - Dec 20
Deluxe studio with kitchenette, furnished lanai, pool, & hot tub
BBQ/picnic area
Aston Waikiki Sunset

Aston Waikiki Sunset

4.0 star property
Waikiki
7.8 out of 10, Good, (3051)
"Room was clean with all you need and more, staff was very nice and the hotel has a great pool, great views and perfectly located to get around the island."
United States
Arun
The price is ￥23,834
￥34,567 total
includes taxes & fees
Dec 10 - Dec 11
Aston Waikiki Sunset
Beach nearby, white sand, sun loungers, beach umbrellas
Diamond Head and Partial Ocean views with 2 Beds and Parking

Diamond Head and Partial Ocean views with 2 Beds and Parking

3.5 star property
Waikiki
9.4 out of 10, Exceptional, (32)
"An amazing place to stay. Location parking and communication was beyond our expectations Loved it so much!!! We will definitely be back "
United States
Rodolfo
The price is ￥19,958
￥62,497 total
includes taxes & fees
Nov 28 - Nov 29
Diamond Head and Partial Ocean views with 2 Beds and Parking
Exterior
Relaxing Ocean View Boutique Condo - 20th FL

Relaxing Ocean View Boutique Condo - 20th FL

Waikiki
9.4 out of 10, Exceptional, (72)
"Clean, bright, has most everything you need. Perfect location. "
United States
Matthew D.
The price is ￥10,936
￥34,602 total
includes taxes & fees
Dec 9 - Dec 10
Relaxing Ocean View Boutique Condo - 20th FL
Beach nearby, sun loungers
1-bedroom apartment just 11 minutes walk to Ala Moana Center

1-bedroom apartment just 11 minutes walk to Ala Moana Center

Waikiki
9.6 out of 10, Exceptional, (25)
"We thoroughly enjoyed our stay at this property. Its location is perfect. A 10 minute walk from Ala Moana mall and just a 10 minute walk to the beach. Gigi is a wonderful host and I would recommend this property to everyone. "
United States
Scott C.
The price is ￥13,898
￥59,284 total
includes taxes & fees
Nov 28 - Nov 29
1-bedroom apartment just 11 minutes walk to Ala Moana Center
Iron/ironing board, free WiFi, bed sheets
Partial Ocean King Studio with Kitchenette, AC, and Free WIFI!

Partial Ocean King Studio with Kitchenette, AC, and Free WIFI!

Waikiki
9.8 out of 10, Exceptional, (29)
"Great location and lovely service! Shout out to the staff that were so kind and welcoming during our stay. "
United States
Sorah P.
The price is ￥19,052
￥58,165 total
includes taxes & fees
Nov 30 - Dec 1
Partial Ocean King Studio with Kitchenette, AC, and Free WIFI!
Lobby
Charming cozy condo in marvelous Honolulu with WiFi

Charming cozy condo in marvelous Honolulu with WiFi

2.0 star property
Waikiki
9.6 out of 10, Exceptional, (19)
"Wonderful property. "
United States
Chris T.
The price is ￥12,514
￥36,951 total
includes taxes & fees
Nov 30 - Dec 1
Charming cozy condo in marvelous Honolulu with WiFi
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kailua Hotel Reviews

Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

10/10 Excellent
"We had an amazing family vacation at Sheraton Waikīkī. From the staff, to the clean spacious room, the pool, convenience of being next to the beach, the games in the lobby, we truly enjoyed it all"
Media 6-night trip
Posted 2 days ago
Sheraton Waikiki Beach Resort

Find out more about Kailua

Search for holiday rentals in Kailua on Expedia! You can easily find your home rentals, villas, holiday apartments in Kailua using one of the methods below:

  • View our selection of featured holiday rentals in Kailua
  • Use the map to find apartments and other holiday homes in the Kailua neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Kailua while they last

Look no further and take a look at our great range of rental properties in Kailua!

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?

Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!: This Kailua vacation home rental offers an outdoor pool, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind. Other favorite homes for rent in Kailua are Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa. and BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY.

How many vacation rentals are there in Kailua?

With 161 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.