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Kailua Holiday Rentals

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Our top choices for Kailua holiday rentals

1. Luxury Beachfront Condo with View

Luxury Beachfront Condo with View
Hauula
9.6 out of 10, Exceptional, (103 reviews)
"Ideal location for island exploring and an amazing view for evenings and early mornings. We had two young kids and the stay was perfect for a family of 4. Even though the building was undergoing renovations during the stay, the disruption was minimal for our unit."
United States
Dale S.
Luxury Beachfront Condo with View

2. 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, (53 reviews)
"Great place. Very clean and close to PCC"
United States
Jordan S.
The price is NZ$1,239
includes taxes & fees
26 Sept - 27 Sept
Mea Kanu Paradise, Beach Access, AC, Sleep up to 6

3. Beachfront Condo with Beach Access & Pool

Beachfront Condo with Beach Access & Pool
Hauula
9.4 out of 10, Exceptional, (44 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 NZ$1,307
includes taxes & fees
16 Oct - 17 Oct
Beachfront Condo with Beach Access & Pool

4. "Hina Hideaway", Views, A/C, ~5 min Walk to Beach

"Hina Hideaway", Views, A/C, ~5 min Walk to Beach
Punaluu
10.0 out of 10, Exceptional, (53 reviews)
"Perfect place to visit North Shore. Close to lots of great things to do. Perfect view of ocean. "
United States
David P.
The price is NZ$1,235
includes taxes & fees
28 Sept - 29 Sept
"Hina Hideaway", Views, A/C, ~5 min Walk to Beach

5. Beachfront Penthouse w/ 3 Lanais on O’ahu!

Beachfront Penthouse w/ 3 Lanais on O’ahu!
Hauula
9.4 out of 10, Exceptional, (111 reviews)
"The condo was just as described! Fantastic views"
United States
Julie D.
Beachfront Penthouse w/ 3 Lanais on O’ahu!

6. Bishop Suites Downtown Honolulu

Bishop Suites Downtown Honolulu
4.0 star property
Downtown Honolulu
7.8 out of 10, Good, (155 reviews)
"Loved this stay! So spacious! Great views"
United States
Callie
The price is NZ$387
includes taxes & fees
1 Oct - 2 Oct
Bishop Suites Downtown Honolulu

7. Aston Waikiki Sunset

Aston Waikiki Sunset
4.0 star property
Waikiki
7.8 out of 10, Good, (3,282 reviews)
"It was a pleasant stay… I’m definitely coming back."
United States
andrea
The price is NZ$392
includes taxes & fees
14 Oct - 15 Oct
Aston Waikiki Sunset

8. Diamond Head and Ocean views with King Bed and Parking

Diamond Head and Ocean views with King Bed and Parking
3.5 star property
Waikiki
9.6 out of 10, Exceptional, (21 reviews)
The price is NZ$863
includes taxes & fees
2 Oct - 3 Oct
Diamond Head and Ocean views with King Bed and Parking

9. Skyline Island Colony Hotel

Skyline Island Colony Hotel
3.0 star property
Waikiki
7.2 out of 10, Good, (2,299 reviews)
"Great place"
United States
Iurii
The price is NZ$285
includes taxes & fees
28 Sept - 29 Sept
Skyline Island Colony Hotel

10. Awesome view. Walking distance to beach, restaurants, shopping

Awesome view. Walking distance to beach, restaurants, shopping
Waikiki
9.4 out of 10, Exceptional, (32 reviews)
"Great location and view"
United States
Tarin K.
The price is NZ$506
includes taxes & fees
28 Sept - 29 Sept
Awesome view. Walking distance to beach, restaurants, shopping

11. Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi

Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi
Waikiki
9.0 out of 10, Wonderful, (135 reviews)
"Really convenient location, a beautiful view, comfortable amenities. Pleasant and helpful communication with host."
United States
April B.
The price is NZ$461
includes taxes & fees
3 Oct - 4 Oct
Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi

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

Cozy condo at Hawaiian monarch- no resort fee, free parking, near beaches, shop
Waikiki
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful place and wonderful host! Will come again."
United States
AVenture
The price is NZ$494
includes taxes & fees
29 Sept - 30 Sept
Cozy condo at Hawaiian monarch- no resort fee, free parking, near beaches, shop

13. King Bed • Renovated • Canal & Mountain View • Walk to Beach

King Bed • Renovated • Canal & Mountain View • Walk to Beach
Waikiki
9.6 out of 10, Exceptional, (67 reviews)
"Clean space, great location, very responsive host. Would gladly stay here again!"
United States
Emily K.
The price is NZ$575
includes taxes & fees
8 Oct - 9 Oct
King Bed • Renovated • Canal & Mountain View • Walk to Beach

14. NEW Fall Deal Walk to Waikiki Beach from a Cool City Studio

NEW Fall Deal Walk to Waikiki Beach from a Cool City Studio
Waikiki
9.4 out of 10, Exceptional, (77 reviews)
"Stayed here for 20 days. Great location and a block away from the beach."
United States
Arpita B.
The price is NZ$855
includes taxes & fees
26 Sept - 27 Sept
NEW Fall Deal Walk to Waikiki Beach from a Cool City Studio

15. Ilikai Marina Vacations

Ilikai Marina Vacations
3.0 star property
Waikiki
8.6 out of 10, Excellent, (54 reviews)
"Nice place. Maybe a little attention to cleanliness. Other than that everything is perfect and location is really good."
United States
Dorin
The price is NZ$615
includes taxes & fees
1 Oct - 2 Oct
Ilikai Marina Vacations

16. **Diamond Head, Ocean, and Park Views**

**Diamond Head, Ocean, and Park Views**
Waikiki
9.0 out of 10, Wonderful, (32 reviews)
"Everything was great! Awesome location!"
United States
Kristina S.
The price is NZ$693
includes taxes & fees
8 Oct - 9 Oct
**Diamond Head, Ocean, and Park Views**

17. Aston at the Waikiki Banyan

Aston at the Waikiki Banyan
3.0 star property
Waikiki
7.4 out of 10, Good, (2,769 reviews)
"The check in was easy and they even let us check in a few hours early when we only meant to drop off luggage. Room was clean and large- a little older style but roomy with great view.parking was plentiful. Great location to everything. The people at desk and parking were so nice. Have stayed there before will return!"
United States
Jocelyn
The price is NZ$393
includes taxes & fees
21 Oct - 22 Oct
Aston at the Waikiki Banyan

18. 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
9.2 out of 10, Wonderful, (41 reviews)
"It was a nice stay"
United States
Charles P
The price is NZ$955
includes taxes & fees
3 Oct - 4 Oct
Diamond Head and Partial Ocean views with 2 Beds and Parking

19. Corner Unit Studio@Waikiki Hotel Building 1 day min

Corner Unit Studio@Waikiki Hotel Building 1 day min
Waikiki
8.2 out of 10, Very good, (108 reviews)
"Good location, easy check in and out"
United States
Manuel
The price is NZ$460
includes taxes & fees
1 Oct - 2 Oct
Corner Unit Studio@Waikiki Hotel Building 1 day min

20. Renovated Specious Studio with Great View

Renovated Specious Studio with Great View
Waikiki
9.0 out of 10, Wonderful, (52 reviews)
"Ash was excellent in communicating. He even allowed us early entry which was so appreciated as we had flown from Calgary to Vancouver to Honolulu and were very sleep deprived!"
Canada
John
The price is NZ$369
includes taxes & fees
17 Oct - 18 Oct
Renovated Specious Studio with Great View
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kailua holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Kailua. 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 Kailua. 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 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 holiday 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 Kailua short-term rentals, that won’t be hard to do.

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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. Other favourite homes for rent in Kailua are Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa. and BEST LICENSED LOCATION The VIEWHOUSE LANIKAI Aalapapa 43005029, 07018,10701878.

How many holiday rentals are there in Kailua?

With 139 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?

Kalama Beach Park 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 Ala Moana Center and Waikiki Beach Walk 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.