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Kailua Vacation Rentals

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Our top choices for Kailua vacation rentals

1. Aston Waikiki Sunset

Aston Waikiki Sunset
4.0 star property
Waikiki
7.8 out of 10, Good, (3,263 reviews)
"It was great stay very convenient close to the beach and everything at short walking distance."
United States
Daniel
The price is CA $243
CA $346 total
includes taxes & fees
Sep 3 - Sep 4
Aston Waikiki Sunset

2. 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, (41 reviews)
"Overall experience was great free parking walking distance to the beach plenty of places to keep busy 👍"
United States
Erwin
The price is CA $197
CA $611 total
includes taxes & fees
Aug 29 - Aug 30
Partial Ocean View Condo with King or Queen Bed and Parking

3. Marriott Vacation Club, Waikiki

Marriott Vacation Club, Waikiki
4.0 star property
Waikiki
9.6 out of 10, Exceptional, (184 reviews)
"Convenient walk to the beach, respectful guests throughout, clean space and amazing view from the pool!"
United States
Eliza Mikiye Kawazoye
The price is CA $453
CA $538 total
includes taxes & fees
Sep 10 - Sep 11
Marriott Vacation Club, Waikiki

4. Skyline Island Colony Hotel

Skyline Island Colony Hotel
3.0 star property
Waikiki
7.2 out of 10, Good, (2,291 reviews)
"Staff was super nice"
United States
Luis
The price is CA $165
CA $253 total
includes taxes & fees
Aug 31 - Sep 1
Skyline Island Colony Hotel

5. Regency on Beachwalk Waikiki by OUTRIGGER

Regency on Beachwalk Waikiki by OUTRIGGER
3.5 star property
Waikiki
8.4 out of 10, Very good, (478 reviews)
"Great room, friendly staff and great location"
United States
Julian
The price is CA $394
CA $1,040 total
includes taxes & fees
Sep 26 - Sep 27
Regency on Beachwalk Waikiki by OUTRIGGER

6. Panoramic Oceanview Resort

Panoramic Oceanview Resort
4.0 star property
Waikiki
9.0 out of 10, Wonderful, (28 reviews)
"The Panaramic Ocean View Resort was a great choice! Absolutely wonderful place to stay. It's a great location with a great view. Lots to do within walking distance. The room was spacious with all you need. Our nine nights were incredible!"
United States
John
The price is CA $548
CA $981 total
includes taxes & fees
Sep 8 - Sep 9
Panoramic Oceanview Resort

7. Skyline Island Stay-2 Adjoining Studios

Skyline Island Stay-2 Adjoining Studios
3.0 star property
Waikiki
8.0 out of 10, Very good, (5 reviews)
"Great location and stay!! Had everything we needed and more. Was comfortable and easy."
United States
Alex
The price is CA $273
CA $669 total
includes taxes & fees
Sep 4 - Sep 5
Skyline Island Stay-2 Adjoining Studios

8. King Bed Studio with Rooftop Pool and Hot Tub

King Bed Studio with Rooftop Pool and Hot Tub
Waikiki
9.4 out of 10, Exceptional, (26 reviews)
"Great location, not too far from the beach. Our room was extremely clean and had all the amenities we needed"
United States
Nikki Q.
The price is CA $383
CA $989 total
includes taxes & fees
Aug 29 - Aug 30
King Bed Studio with Rooftop Pool and Hot Tub

9. 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, (68 reviews)
"Great host communication, well appointeded unit, ideal location and amenities."
United States
Brian S.
The price is CA $217
CA $677 total
includes taxes & fees
Aug 30 - Aug 31
Waikiki 2 Bedrooms with free parking near beaches, and Ala Moana shopping center

10. Island Colony hotel

Island Colony hotel
2.5 star property
Waikiki
10.0 out of 10, Exceptional, (3 reviews)
"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 CA $169
CA $447 total
includes taxes & fees
Aug 29 - Aug 30
Island Colony hotel

11. Aston at the Waikiki Banyan

Aston at the Waikiki Banyan
3.0 star property
Waikiki
7.2 out of 10, Good, (2,758 reviews)
"Nice and quick staff!! Good location"
United States
Dina
The price is CA $215
CA $308 total
includes taxes & fees
Aug 31 - Sep 1
Aston at the Waikiki Banyan

12. High Floor Ocean View Condo w/ 2 Beds and Parking

High Floor Ocean View Condo w/ 2 Beds and Parking
3.5 star property
Waikiki
9.6 out of 10, Exceptional, (19 reviews)
"Location was perfect with a short walk to the beach, shops and great restaurants."
United States
Ross
The price is CA $255
CA $680 total
includes taxes & fees
Aug 29 - Aug 30
High Floor Ocean View Condo w/ 2 Beds and Parking

13. Premier corner unit w/ocean views, FREE PARKING, NO Resort Fees. Full kitchen.

Premier corner unit w/ocean views, FREE PARKING, NO Resort Fees. Full kitchen.
Waikiki
9.4 out of 10, Exceptional, (43 reviews)
"Amazing clean sea facing property. We enjoyed the pool, hot tub and free parking! Host was super friendly as well!!"
United States
Harsh Vardhan S.
The price is CA $262
CA $718 total
includes taxes & fees
Sep 3 - Sep 4
Premier corner unit w/ocean views, FREE PARKING, NO Resort Fees. Full kitchen.

14. Waikiki condo w/ lanai, pool, & beach access

Waikiki condo w/ lanai, pool, & beach access
Waikiki
9.8 out of 10, Exceptional, (19 reviews)
"Great ocean view and a short walk to the beach, shops, and restaurants. "
United States
Larry W.
The price is CA $475
CA $1,039 total
includes taxes & fees
Sep 26 - Sep 27
Waikiki condo w/ lanai, pool, & beach access

15. Waikiki Shore by OUTRIGGER

Waikiki Shore by OUTRIGGER
3.0 star property
Waikiki
8.2 out of 10, Very good, (600 reviews)
"Room 614. Good location with a view of the water, as the accommodation is on the beachfront. Room had its own washer and dryer, which was fantastic. Close to everything."
Australia
Michael James
The price is CA $431
CA $985 total
includes taxes & fees
Sep 10 - Sep 11
Waikiki Shore by OUTRIGGER

16. New Decor! Oceanfront, Yacht Harbor, Luxury, Friday Fireworks front row, FAB!

New Decor! Oceanfront, Yacht Harbor, Luxury, Friday Fireworks front row, FAB!
Waikiki
9.4 out of 10, Exceptional, (205 reviews)
"This was a beautiful and really clean condo! The view was gorgeous. Front row to amazing sunsets and the Friday night fireworks. The bed was so, so comfortable, and I slept so soundly. The host was really nice and communicated well with us. Highly recommend this place! "
United States
Lori C.
The price is CA $276
CA $690 total
includes taxes & fees
Sep 3 - Sep 4
New Decor! Oceanfront, Yacht Harbor, Luxury, Friday Fireworks front row, FAB!

17. Waikiki Banyan,1BR, Sleeps 4, Full Kitchen, FREE PARKING, NO RESORT FEES

Waikiki Banyan,1BR, Sleeps 4, Full Kitchen, FREE PARKING, NO RESORT FEES
Waikiki
9.6 out of 10, Exceptional, (198 reviews)
"Room was very clean and comfortable. Great location for what we had planned for the stay."
United States
Elden E.
The price is CA $281
CA $744 total
includes taxes & fees
Sep 12 - Sep 13
Waikiki Banyan,1BR, Sleeps 4, Full Kitchen, FREE PARKING, NO RESORT FEES

18. ILIKAI 19th FL OCEAN VIEW - GREAT VALUE!

ILIKAI 19th FL OCEAN VIEW - GREAT VALUE!
Waikiki
9.8 out of 10, Exceptional, (115 reviews)
"We had the best week, thank you! Room was exactly what was on the link as advertised. Enjoyed staying at Ilikia… can’t wait to one day return!!! "
United States
Misty S.
The price is CA $249
CA $1,101 total
includes taxes & fees
Sep 10 - Sep 11
ILIKAI 19th FL OCEAN VIEW - GREAT VALUE!

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

Waikiki Oceanfront/Beachfront Condo. Breathtaking views. Walk to everything!
Waikiki
9.4 out of 10, Exceptional, (82 reviews)
"Nice view of the harbor and the ocean further out."
United States
J&A N.
The price is CA $239
CA $641 total
includes taxes & fees
Aug 30 - Aug 31
Waikiki Oceanfront/Beachfront Condo. Breathtaking views. Walk to everything!

20. 2 SIDE BY SIDE CONDOS 2 BLOCKS FROM THE BEACH! LOTS OF SLEEPING SPACE!

2 SIDE BY SIDE CONDOS 2 BLOCKS FROM THE BEACH! LOTS OF SLEEPING SPACE!
Waikiki
9.6 out of 10, Exceptional, (57 reviews)
"Great rooms and great AC. "
United States
James R.
The price is CA $560
CA $1,374 total
includes taxes & fees
Sep 10 - Sep 11
2 SIDE BY SIDE CONDOS 2 BLOCKS FROM THE BEACH! LOTS OF SLEEPING SPACE!
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 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.

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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?

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY: This Kailua vacation home rental is located on the beach and has a balcony, a private yard, 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. 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 138 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 Walk 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.