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Kailua Vacation Rentals

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Our top choices for Kailua vacation rentals

1. Luxurious five-bedroom modern retreat

Luxurious five-bedroom modern retreat
Enchanted Lake
8.8 out of 10, Excellent, (5 reviews)
"Great communication with host - property as advertised- we had a great stay"
United States
Wytske K.
The price is CA $827
CA $2,302 total
includes taxes & fees
Aug 22 - Aug 23
Luxurious five-bedroom modern retreat

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, (52 reviews)
"Great place. Very clean and close to PCC"
United States
Jordan S.
Mea Kanu Paradise, Beach Access, AC, Sleep up to 6

3. Luxury Beachfront Condo with Ocean View

Luxury Beachfront Condo with Ocean View
Hauula
9.2 out of 10, Wonderful, (49 reviews)
"Great location and beautiful scenery "
United States
Heather K.
The price is CA $453
CA $1,147 total
includes taxes & fees
Sep 8 - Sep 9
Luxury Beachfront Condo with Ocean View

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, (54 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 CA $390
CA $1,029 total
includes taxes & fees
Sep 1 - Sep 2
"Hina Hideaway", Views, A/C, ~5 min Walk to Beach

5. Aston Waikiki Sunset

Aston Waikiki Sunset
4.0 star property
Waikiki
7.8 out of 10, Good, (3,259 reviews)
"It was great stay very convenient close to the beach and everything at short walking distance."
United States
Daniel
The price is CA $236
CA $337 total
includes taxes & fees
Aug 26 - Aug 27
Aston Waikiki Sunset

6. Marriott Vacation Club, Waikiki

Marriott Vacation Club, Waikiki
4.0 star property
Waikiki
9.6 out of 10, Exceptional, (183 reviews)
"Very friendly staff and a great location. Right in the heart of the shopping district 5 minute walk to the beach."
United States
NICHOLAS
The price is CA $451
CA $535 total
includes taxes & fees
Aug 29 - Aug 30
Marriott Vacation Club, Waikiki

7. 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 $317
CA $751 total
includes taxes & fees
Aug 22 - Aug 23
Partial Ocean View Condo with King or Queen Bed and Parking

8. Bishop Suites At The Executive Centre

Bishop Suites At The Executive Centre
4.0 star property
Downtown Honolulu
7.8 out of 10, Good, (146 reviews)
"The staff we encountered were very helpful and friendly."
United States
Robert
The price is CA $240
CA $326 total
includes taxes & fees
Sep 2 - Sep 3
Bishop Suites At The Executive Centre

9. Royal Kuhio

Royal Kuhio
3.5 star property
Waikiki
8.6 out of 10, Excellent, (616 reviews)
"Great location"
United States
Rodolfo Luz
Royal Kuhio

10. Skyline Island Colony Hotel

Skyline Island Colony Hotel
3.0 star property
Waikiki
7.2 out of 10, Good, (2,286 reviews)
"Staff was super nice"
United States
Luis
The price is CA $145
CA $229 total
includes taxes & fees
Sep 21 - Sep 22
Skyline Island Colony Hotel

11. Waikiki Shore by OUTRIGGER

Waikiki Shore by OUTRIGGER
3.0 star property
Waikiki
8.4 out of 10, Very good, (596 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 $441
CA $995 total
includes taxes & fees
Aug 22 - Aug 23
Waikiki Shore by OUTRIGGER

12. Ilikai Marina Vacations

Ilikai Marina Vacations
3.0 star property
Waikiki
8.6 out of 10, Excellent, (50 reviews)
"This condo is close to the Ilikai and Hilton Hawaiian Village. Also very near the Trolley stops. Conveniently located near the Ala Moana mall. The condo has everything you need. A small kitchen with a stove, microwave and refrigerator. Highly recommend."
United States
Gina
The price is CA $146
CA $476 total
includes taxes & fees
Aug 29 - Aug 30
Ilikai Marina Vacations

13. 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 $539
CA $967 total
includes taxes & fees
Sep 16 - Sep 17
Panoramic Oceanview Resort

14. Tropical Studios at Marine Surf Waikiki

Tropical Studios at Marine Surf Waikiki
3.0 star property
Waikiki
8.4 out of 10, Very good, (377 reviews)
"Geselle was so nice and help us with some of our need. Will recommend this place to our friend."
United States
WILLIAM Tomas
The price is CA $153
CA $345 total
includes taxes & fees
Sep 2 - Sep 3
Tropical Studios at Marine Surf Waikiki

15. Aston at the Waikiki Banyan

Aston at the Waikiki Banyan
3.0 star property
Waikiki
7.2 out of 10, Good, (2,757 reviews)
"Nice and quick staff!! Good location"
United States
Dina
The price is CA $219
CA $313 total
includes taxes & fees
Aug 23 - Aug 24
Aston at the Waikiki Banyan

16. Near WAIKIKI Beach, FREE parking, POOL View, Sleep 6

Near WAIKIKI Beach, FREE parking, POOL View, Sleep 6
Waikiki
9.8 out of 10, Exceptional, (46 reviews)
"Awesome spot. Location, amenities, communication. Thank you. "
United States
Kimera H.
Near WAIKIKI Beach, FREE parking, POOL View, Sleep 6

17. Premium Remodeled Condo with Ocean View and Parking

Premium Remodeled Condo with Ocean View and Parking
4.0 star property
Waikiki
9.4 out of 10, Exceptional, (39 reviews)
"Very relaxing and great location!"
United States
David
The price is CA $329
CA $766 total
includes taxes & fees
Aug 25 - Aug 26
Premium Remodeled Condo with Ocean View and Parking

18. High-rise retreat w/ ocean & mountain views

High-rise retreat w/ ocean & mountain views
Waikiki
9.6 out of 10, Exceptional, (43 reviews)
"We loved everything about our stay in this apartment . Great location and great facilities"
New Zealand
malachi b.
The price is CA $445
CA $1,017 total
includes taxes & fees
Sep 4 - Sep 5
High-rise retreat w/ ocean & mountain views

19. 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 $346
CA $935 total
includes taxes & fees
Aug 23 - Aug 24
King Bed Studio with Rooftop Pool and Hot Tub

20. 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)
"The place was cozy and just perfect for a few days! Little extras for the beach and making light meals, so awesome! It was quiet, the AC worked well and the shower and water pressure very nice. Host is so responsive and helpful. Access to pool and the 2 hot tubs with no resort fee."
United States
Siobhan K.
Cozy condo at Hawaiian monarch- no resort fee, free parking, near beaches, shop
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?

Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.: This Kailua vacation home rental is located near the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Kailua are BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY 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?

Lanikai Beach and Kalama Beach Park 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.