Kailua Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Kailua vacation rentals

5 bedrooms, iron/ironing board, travel crib, WiFi

Luxurious five-bedroom modern retreat

Luxurious five-bedroom modern retreat
Enchanted Lake
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 ￥215,015
￥409,832 total
includes taxes & fees
Jun 13 - Jun 14
Luxurious five-bedroom modern retreat
On the beach

Beachfront Condo with Lanai and View

Beachfront Condo with Lanai and View
Hauula
10.0 out of 10, Exceptional, (3 reviews)
"Amazing location, had every amenity imaginable and so clean! "
United States
Jessica
The price is ￥40,136
￥110,404 total
includes taxes & fees
Jun 21 - Jun 22
Beachfront Condo with Lanai and View
Beach nearby

Mea Kanu Paradise, Beach Access, AC, Sleep up to 6

Mea Kanu Paradise, Beach Access, AC, Sleep up to 6
Hauula
9.8 out of 10, Exceptional, (48 reviews)
"Nice accommodation for a family. Nice size closets 1.5 bath, washers and dryer, and close to shopping. Beach access within walking distance is not appropriate for young children. We would stay here again. Polynesian Cultural Center is only 5-8 minutes away by car. Host was easy to work with."
United States
Ray K.
The price is ￥40,455
￥109,527 total
includes taxes & fees
Jun 2 - Jun 3
Mea Kanu Paradise, Beach Access, AC, Sleep up to 6
On the beach

Luxury Beachfront Condo with Ocean View

Luxury Beachfront Condo with Ocean View
Hauula
9.4 out of 10, Exceptional, (47 reviews)
"Great location and beautiful scenery "
United States
Heather K.
The price is ￥50,648
￥128,472 total
includes taxes & fees
Jun 16 - Jun 17
Luxury Beachfront Condo with Ocean View
On the beach

Beachfront Condo with Beach Access & Pool

Beachfront Condo with Beach Access & Pool
Hauula
9.6 out of 10, Exceptional, (42 reviews)
"Great communication. Super clean! Construction didn’t impact us at all. The view is absolutely beautiful! We would not hesitate to book this unit again! "
United States
Julie C.
The price is ￥78,839
￥167,005 total
includes taxes & fees
Jun 20 - Jun 21
Beachfront Condo with Beach Access & Pool
On the beach

Luxury Beachfront Condo with View

Luxury Beachfront Condo with View
Hauula
9.8 out of 10, Exceptional, (100 reviews)
"Very nice accommodations "
United States
Cassandra C.
The price is ￥54,630
￥133,663 total
includes taxes & fees
Jun 16 - Jun 17
Luxury Beachfront Condo with View
On the beach

Beachfront Penthouse w/ 3 Lanais on O’ahu!

Beachfront Penthouse w/ 3 Lanais on O’ahu!
Hauula
9.4 out of 10, Exceptional, (108 reviews)
"The condo was just as described! Fantastic views"
United States
Julie D.
The price is ￥60,841
￥233,420 total
includes taxes & fees
Jun 24 - Jun 25
Beachfront Penthouse w/ 3 Lanais on O’ahu!
Beach nearby, white sand, sun loungers, beach umbrellas

Partial Ocean View Condo with King or Queen Bed and Parking

Partial Ocean View Condo with King or Queen Bed and Parking
3.5 star property
Waikiki
9.6 out of 10, Exceptional, (36 reviews)
"The property is so beautiful. I loved our stay. We stayed with 2 kids and it felt like home for us. Loved how accessible it is to beach. Not just beach but also to ala wai walking trail. With free parking this is a jackpot. So wonderful. I would definitely recommend this place to anyone."
United States
Amruthaa
The price is ￥32,013
￥66,365 total
includes taxes & fees
Jun 8 - Jun 9
Partial Ocean View Condo with King or Queen Bed and Parking
Apartment, Balcony, Canal View | Pool

Comfy and Modern Condo By Waikiki

Comfy and Modern Condo By Waikiki
3.5 star property
Waikiki
The price is ￥17,240
￥93,617 total
includes taxes & fees
Jun 8 - Jun 9
Comfy and Modern Condo By Waikiki
Apartment (1 Bedroom) | Beach | Private beach, sun loungers, beach umbrellas, beach towels

@ Marbella Lane -coastal Retreat Near Diamond Head

@ Marbella Lane -coastal Retreat Near Diamond Head
2.5 star property
Diamond Head - Kapahulu - St. Louis
The price is ￥36,289
￥71,046 total
includes taxes & fees
Jun 7 - Jun 8
@ Marbella Lane -coastal Retreat Near Diamond Head
Dining

Stunning Ocean View/ Exquisite Renovated Studio/King Bed/Walk to Beach

Stunning Ocean View/ Exquisite Renovated Studio/King Bed/Walk to Beach
Waikiki
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, great location and good communication. "
Australia
Kelly
The price is ￥15,051
￥46,172 total
includes taxes & fees
Jun 1 - Jun 2
Stunning Ocean View/ Exquisite Renovated Studio/King Bed/Walk to Beach
Studio, 1 Queen Bed, Non Smoking, City View 2 | Living area | 32-inch TV with cable channels

Ilikai Marina Vacations

Ilikai Marina Vacations
3.0 star property
Waikiki
8.4 out of 10, Very Good, (43 reviews)
"Had a great stay, the room had everything we needed and more, great location close to everything, for sure coming back again with my whole family:)"
United States
Laura
The price is ￥19,868
￥56,672 total
includes taxes & fees
Jun 8 - Jun 9
Ilikai Marina Vacations
Exterior detail

Aloha Suite Near the Sea III - 2 Block Walk to Beach!

Aloha Suite Near the Sea III - 2 Block Walk to Beach!
Waikiki
10.0 out of 10, Exceptional, (112 reviews)
"Host was very responsive and accommodating, the unit was clean and comfortable, and best of all the location has great access to the beach, restaurants, bus, and so forth. Would stay again!"
United States
Roy K.
The price is ￥12,710
￥46,228 total
includes taxes & fees
Jun 6 - Jun 7
Aloha Suite Near the Sea III - 2 Block Walk to Beach!
Design Studio Suite | Individually decorated, individually furnished, blackout drapes

Marine Surf by Tropical Escapes Realty

Marine Surf by Tropical Escapes Realty
3.0 star property
Waikiki
8.8 out of 10, Excellent, (62 reviews)
"Pretty much at the heart of waikiki. Excellent spot but we went during construction/renovations so it was awfully loud around 10am. But it's not their fault "
United States
Joshua
The price is ￥26,351
￥75,525 total
includes taxes & fees
Jun 4 - Jun 5
Marine Surf by Tropical Escapes Realty
1 bedroom, iron/ironing board, free WiFi, wheelchair access

Waikiki Skyline 28th Floor Hawaiian Monarch

Waikiki Skyline 28th Floor Hawaiian Monarch
Waikiki
9.4 out of 10, Exceptional, (3 reviews)
"We absolutely loved our stay! The location was fantastic—we really enjoyed being right by the Ala Wai Canal. We also loved how close it was to a 7-Eleven and a great food truck spot, which made grabbing snacks and meals super convenient. We hadn’t realized there would be several parades and local events during our visit, which caused some road closures and traffic, but this property’s location made it easy for us to get in and out without any issues. I truly can’t recommend this stay enough. The...
United States
Joe A.
The price is ￥15,768
￥44,018 total
includes taxes & fees
Jun 1 - Jun 2
Waikiki Skyline 28th Floor Hawaiian Monarch
Standard Studio, 1 Queen Bed with Sofa bed, Park View | Terrace/patio

Luana Waikiki by Tropical Escapes Realty

Luana Waikiki by Tropical Escapes Realty
2.5 star property
Waikiki
8.0 out of 10, Very Good, (61 reviews)
"Everything was great! Would definitely recommend. The location was excellent also "
United States
Dawn Marie Cowie
The price is ￥22,720
￥74,996 total
includes taxes & fees
Jun 3 - Jun 4
Luana Waikiki by Tropical Escapes Realty
Sun loungers, beach towels

Waikiki 2 Bedrooms with free parking near beaches, and Ala Moana shopping center

Waikiki 2 Bedrooms with free parking near beaches, and Ala Moana shopping center
Waikiki
9.6 out of 10, Exceptional, (65 reviews)
"Great host communication, well appointeded unit, ideal location and amenities."
United States
Brian S.
The price is ￥25,491
￥77,806 total
includes taxes & fees
Jun 6 - Jun 7
Waikiki 2 Bedrooms with free parking near beaches, and Ala Moana shopping center
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, (37 reviews)
"It was a nice stay"
United States
Charles P
The price is ￥32,332
￥66,744 total
includes taxes & fees
Jun 5 - Jun 6
Diamond Head and Partial Ocean views with 2 Beds and Parking
Pool

Waikiki Stay 1 BR w/Kitchen, 2 blocks from the beach

Waikiki Stay 1 BR w/Kitchen, 2 blocks from the beach
Waikiki
9.8 out of 10, Exceptional, (17 reviews)
"Great location 4 min away from the beach. Grocery, drinks and restaurants very close by. We had a great time!"
Canada
Christian
The price is ￥21,358
￥70,373 total
includes taxes & fees
Jun 7 - Jun 8
Waikiki Stay 1 BR w/Kitchen, 2 blocks from the beach
Exterior

Waikiki 22nd Floor Studio Ocean & Mountain Views

Waikiki 22nd Floor Studio Ocean & Mountain Views
Waikiki
9.6 out of 10, Exceptional, (4 reviews)
"Everything was great and super easy host was great at communicating and answering right away. "
United States
Ruth
The price is ￥13,761
￥39,435 total
includes taxes & fees
Jun 11 - Jun 12
Waikiki 22nd Floor Studio Ocean & Mountain Views
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.
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Top Kailua Hotel Reviews

Hyatt Regency Waikiki Beach Resort & Spa

Hyatt Regency Waikiki Beach Resort & Spa

10/10 Excellent
"Clean room the beach view was amazing"
kidst 2-night trip
Posted 1 hour ago
Hyatt Regency Waikiki Beach Resort & Spa

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
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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?

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 Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa. and Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!.

How many vacation rentals are there in Kailua?

With 142 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?

Kalama Beach Park and Kailua Bay 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.