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Kailua Holiday Rentals

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Our top choices for Kailua holiday rentals

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 NZ$4,638
includes taxes & fees
30 June - 1 July
Luxurious five-bedroom modern retreat

Comfy and Modern Condo By Waikiki

Comfy and Modern Condo By Waikiki
3.5 star property
Waikiki
The price is NZ$659
includes taxes & fees
30 June - 1 July
Comfy and Modern Condo By Waikiki

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 NZ$1,322
includes taxes & fees
2 July - 3 July
Luxury Beachfront Condo with Ocean View

Ilikai Marina Vacations

Ilikai Marina Vacations
3.0 star property
Waikiki
8.4 out of 10, Very good, (44 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 NZ$616
includes taxes & fees
29 June - 30 June
Ilikai Marina Vacations

"Hina Hideaway", Views, AC, Walkable to Beach

"Hina Hideaway", Views, AC, Walkable to Beach
Punaluu
10.0 out of 10, Exceptional, (51 reviews)
"Great communication and wonderful place. "
United States
Nathan H.
The price is NZ$1,609
includes taxes & fees
12 July - 13 July
"Hina Hideaway", Views, AC, Walkable to Beach

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, (49 reviews)
"Great place. Very clean and close to PCC"
United States
Jordan S.
The price is NZ$1,375
includes taxes & fees
29 June - 30 June
Mea Kanu Paradise, Beach Access, AC, Sleep up to 6

Skyline Island Stay-2 Adjoining Studios

Skyline Island Stay-2 Adjoining Studios
3.0 star property
Waikiki
2.0 out of 10, (1 review)
The price is NZ$706
includes taxes & fees
29 June - 30 June
Skyline Island Stay-2 Adjoining Studios

Panoramic Oceanview Resort

Panoramic Oceanview Resort
4.0 star property
Waikiki
9.4 out of 10, Exceptional, (23 reviews)
"Great stay with beautiful beaches! Only complaint only 4 towels for an entire week with 4 guest"
United States
Dena
The price is NZ$1,175
includes taxes & fees
28 June - 29 June
Panoramic Oceanview Resort

Luxury Beachfront Condo with View

Luxury Beachfront Condo with View
Hauula
9.8 out of 10, Exceptional, (101 reviews)
"Very nice accommodations "
United States
Cassandra C.
Luxury Beachfront Condo with View

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

Cozy condo at Hawaiian monarch- no resort fee, near beaches, shop
Waikiki
9.8 out of 10, Exceptional, (36 reviews)
"Location was ideal as it was close to many things and across the street from great food trucks. The parking was a bit of a hike but nice that it was included in the price of the room. Condo was small but kept up well."
United States
Kim S.
The price is NZ$492
includes taxes & fees
20 July - 21 July
Cozy condo at Hawaiian monarch- no resort fee, near beaches, shop

Remodeled Awesome View Waikiki Studio with Full Kitchen

Remodeled Awesome View Waikiki Studio with Full Kitchen
Waikiki
10.0 out of 10, Exceptional, (2 reviews)
"The room was so clean, easy to access and great location. You are able to walk to basically anywhere. "
Canada
Sabrina G.
The price is NZ$518
includes taxes & fees
3 July - 4 July
Remodeled Awesome View Waikiki Studio with Full Kitchen

@ 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 NZ$1,002
includes taxes & fees
13 July - 14 July
@ Marbella Lane -coastal Retreat Near Diamond Head

Relaxing Ocean View Boutique Condo - 20th FL

Relaxing Ocean View Boutique Condo - 20th FL
Waikiki
9.2 out of 10, Wonderful, (82 reviews)
"Great location to explore Waikīkī!"
United States
David N.
The price is NZ$447
includes taxes & fees
11 July - 12 July
Relaxing Ocean View Boutique Condo - 20th FL

Luana Waikiki by Tropical Escapes Realty

Luana Waikiki by Tropical Escapes Realty
2.5 star property
Waikiki
8.0 out of 10, Very good, (62 reviews)
"Everything was great! Would definitely recommend. The location was excellent also "
United States
Dawn Marie Cowie
The price is NZ$822
includes taxes & fees
7 July - 8 July
Luana Waikiki by Tropical Escapes Realty

Diamond Head Beach - Large Studio - Queen Bed, Balcony, Ocean View, Ocean Access

Diamond Head Beach - Large Studio - Queen Bed, Balcony, Ocean View, Ocean Access
Diamond Head - Kapahulu - St. Louis
9.8 out of 10, Exceptional, (101 reviews)
"Enjoyed the location."
United States
kirk b.
The price is NZ$554
includes taxes & fees
12 July - 13 July
Diamond Head Beach - Large Studio - Queen Bed, Balcony, Ocean View, Ocean Access

Bishop Suites At The Executive Centre

Bishop Suites At The Executive Centre
4.0 star property
Downtown Honolulu
7.6 out of 10, Good, (131 reviews)
"Lovely staff!! Nice set up!! Beautiful views!"
United States
Karley
The price is NZ$396
includes taxes & fees
29 June - 30 June
Bishop Suites At The Executive Centre

Waikiki Oceanfront/Beachfront Condo. Breathtaking views. Walk to everything!

Waikiki Oceanfront/Beachfront Condo. Breathtaking views. Walk to everything!
Waikiki
9.2 out of 10, Wonderful, (79 reviews)
"Nice view of the harbor and the ocean further out."
United States
J&A N.
The price is NZ$909
includes taxes & fees
17 July - 18 July
Waikiki Oceanfront/Beachfront Condo. Breathtaking views. Walk to everything!

Little Paradise in Waikiki with Lovely Ocean -15th FL

Little Paradise in Waikiki with Lovely Ocean -15th FL
Waikiki
9.0 out of 10, Wonderful, (45 reviews)
"Clean and good access to shops and restaurant's."
United States
Kim S.
The price is NZ$415
includes taxes & fees
12 July - 13 July
Little Paradise in Waikiki with Lovely Ocean -15th FL

Island Colony hotel

Island Colony hotel
2.5 star property
Waikiki
10.0 out of 10, Exceptional, (1 review)
"The only down side is the parking structure as I paid for 5 days but could not park in it on 1 of the nights."
United States
Jesus
The price is NZ$522
includes taxes & fees
8 July - 9 July
Island Colony hotel

A Cozy and Romantic Studio at Heart of Waikiki

A Cozy and Romantic Studio at Heart of Waikiki
Waikiki
9.6 out of 10, Exceptional, (18 reviews)
"Had an everything we needed, close to everything and great pool and hot tub area.Great three days before our cruise."
United States
Sandra B.
The price is NZ$463
includes taxes & fees
28 June - 29 June
A Cozy and Romantic Studio at Heart of Waikiki
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

Find out more about Kailua

Everything you need to know about Kailua holiday rentals

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

Kailua holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kailua holiday rentals we have selected for you start as low as NZ$308 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 holiday 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 holiday.

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. 

Explore a world of travel with Expedia

Frequently asked questions

Are there holiday rentals in Kailua?

Yes, there are holiday rentals close to the most popular sights in Kailua, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the popular beaches in Kailua.

What are some of the best holiday rentals that Kailua has to offer?

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY: This highly rated holiday home rental in Kailua is located on the beach, and has a balcony, a private garden and air conditioning 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Another good choice for your trip to Kailua is Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!.

How many holiday rentals are there in Kailua?

With 138 Expedia holiday rentals, you're guaranteed to find just the right place for your Kailua stay.

What’s there to see and do in Kailua?

Lanikai Beach and Kailua Bay Beach are a couple of lovely local spots to get outside and enjoy nature. You’ll find favourite places to visit such as Waikiki Beach and Ala Moana Center in the wider area.

What’s a holiday rental in Kailua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kailua. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.