Kailua Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Rentals in Kailua

Our top choices for Kailua vacation rentals

Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!

9.6 out of 10, Exceptional, (203)
"The location is unbeatable: short walk to the best beach! Beds are comfortable. We probably missed the description that the second bathroom is downstairs, outside the unit, but it wasn't a big issue for us. We had a great stay."
Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

9.2 out of 10, Wonderful, (140)
"This is a wonderful place for a family vacation (in my case, three generations). Very well stocked. Steps to a beautiful beach with very few people on it. Paradise!"
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

Aston Waikiki Sunset

4.0 star property
7.8 out of 10, Good, (2976)
"Every thing was great "
The price is CA $186
CA $277 total
includes taxes & fees
Sep 25 - Sep 26
Aston Waikiki Sunset

Skyline Island Colony Hotel

3.0 star property
7.2 out of 10, Good, (2046)
"The hotel provided comfortable beds and great services! We enjoyed our stays. Thank you!"
The price is CA $165
CA $235 total
includes taxes & fees
Aug 27 - Aug 28
Skyline Island Colony Hotel

Aston at the Waikiki Banyan

3.0 star property
7.2 out of 10, Good, (2633)
"Absolutely loved how close it is to the beach "
The price is CA $186
CA $271 total
includes taxes & fees
Sep 25 - Sep 26
Aston at the Waikiki Banyan

Aston Waikiki Beach Tower

4.0 star property
9.2 out of 10, Wonderful, (1774)
"Location of the hotel was perfect "
The price is CA $669
CA $862 total
includes taxes & fees
Sep 16 - Sep 17
Aston Waikiki Beach Tower

Bishop Suites At The Executive Centre

4.0 star property
7.6 out of 10, Good, (59)
"Large living room!"
The price is CA $171
CA $242 total
includes taxes & fees
Aug 31 - Sep 1
Bishop Suites At The Executive Centre

Espacio The Jewel Of Waikiki

5.0 star property
9.6 out of 10, Exceptional, (19)
"The hotel was great, the staff were amazing, and the view from the balcony was beautiful."
The price is CA $3,658
CA $4,316 total
includes taxes & fees
Aug 29 - Aug 30
Espacio The Jewel Of Waikiki

Castle Waikīkī Shore

3.0 star property
8.2 out of 10, Very good, (1198)
"Excellent location and friendly staff. Right on the beach."
Castle Waikīkī Shore

Regency on Beachwalk Waikiki by OUTRIGGER

3.5 star property
8.2 out of 10, Very good, (422)
"Nice little condo/hotel"
Regency on Beachwalk Waikiki by OUTRIGGER

Luana Waikiki by Tropical Escapes Realty

2.5 star property
8.0 out of 10, Very good, (47)
"Great property for families! Clean, quiet, perfect location for everything!!!"
The price is CA $177
CA $454 total
includes taxes & fees
Sep 7 - Sep 8
Luana Waikiki by Tropical Escapes Realty

Hawaiian Sun Holidays

3.0 star property
8.4 out of 10, Very good, (148)
"This was a wonderful place to stay. A bit older and could use some renovations however, the parking was free and it was so close to the beach. We felt safe and comfortable. "
Hawaiian Sun Holidays

Waikiki Shore by OUTRIGGER

3.0 star property
8.4 out of 10, Very good, (530)
"Great location and amazing views. Clean and quiet. Bonus was the Steak Shack on ground level!"
The price is CA $1,668
CA $2,617 total
includes taxes & fees
Sep 25 - Sep 26
Waikiki Shore by OUTRIGGER

Royal Kuhio

3.5 star property
8.6 out of 10, Excellent, (491)
"Good location walking distance to shopping beach and restaurant and free parking. Enjoyed are stay there."
The price is CA $317
CA $374 total
includes taxes & fees
Sep 25 - Sep 26
Royal Kuhio

Premium Remodeled Condo in Waikiki with 2 Beds and Parking

4.0 star property
9.8 out of 10, Exceptional, (6)
"The room was nice, had everything we needed! Awesome views from the lanai and great location to the beach and surrounding shops. We were sad to leave, would definitely stay again! "
The price is CA $281
CA $694 total
includes taxes & fees
Aug 27 - Aug 28
Premium Remodeled Condo in Waikiki with 2 Beds and Parking

High Floor Ocean View Condo (King Bed and Parking)

3.5 star property
9.4 out of 10, Exceptional, (34)
"This was a great property and the location was perfect for a family of 4 to get around and to the beach. I would highly recommend this location if you are staying in Waikiki."
The price is CA $236
CA $633 total
includes taxes & fees
Aug 27 - Aug 28
High Floor Ocean View Condo (King Bed and Parking)

Diamond Head and Ocean views with King Bed and Parking

3.5 star property
9.8 out of 10, Exceptional, (10)
"Great location."
The price is CA $281
CA $694 total
includes taxes & fees
Aug 29 - Aug 30
Diamond Head and Ocean views with King Bed and Parking

Marine Surf by Tropical Escapes Realty

3.0 star property
8.8 out of 10, Excellent, (42)
"I loved this place! Everything we needed was included in the kitchen! I loved that parking was included, and it was right in the heart of waikiki, so everything was super walkable. Will definitely be staying again!"
The price is CA $239
CA $486 total
includes taxes & fees
Aug 27 - Aug 28
Marine Surf by Tropical Escapes Realty

Partial Ocean View Condo with King or Queen Bed and Parking

3.5 star property
9.2 out of 10, Wonderful, (23)
"We had a great time at this property."
The price is CA $219
CA $611 total
includes taxes & fees
Aug 27 - Aug 28
Partial Ocean View Condo with King or Queen Bed and Parking

Ocean View 1BR at Ilikai Marina

3.0 star property
10.0 out of 10, Exceptional, (4)
"This condo was very well renovated and was extremely clean. The view was amazing!"
The price is CA $302
CA $722 total
includes taxes & fees
Aug 31 - Sep 1
Ocean View 1BR at Ilikai Marina
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Kailua Hotel Reviews

Find out more about Kailua

Find out more about Kailua

Everything you need to know about Kailua vacation rentals

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

Kailua vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kailua vacation rentals we have selected for you start as low as CA $165 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 vacation 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 vacation.

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. 

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 fireplace, 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 patio, a garden, and a selection of games so you can immerse yourself in your vacation. Other favorite homes for rent in Kailua are Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more! and Luxurious five-bedroom modern retreat.

How many vacation rentals are there in Kailua?

With 165 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.