Kailua Vacation Rentals

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Our top choices for Kailua vacation 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 CA $1,506
CA $3,132 total
includes taxes & fees
May 24 - May 25
Luxurious five-bedroom modern retreat

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, (48 reviews)
"Nice accommodation for a family. Nice size closets 1.5 bath, washers and dryer, and close to shopping. Beach access within walking distance is not appropriate for young children. We would stay here again. Polynesian Cultural Center is only 5-8 minutes away by car. Host was easy to work with."
United States
Ray K.
The price is CA $408
CA $1,052 total
includes taxes & fees
May 28 - May 29
Mea Kanu Paradise, Beach Access, AC, Sleep up to 6

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

"Hina Hideaway", Views, AC, Walkable to Beach
Punaluu
10.0 out of 10, Exceptional, (49 reviews)
"Amenities are great. Very thoughtful host. "
United States
Manoj N.
The price is CA $523
CA $1,207 total
includes taxes & fees
Jun 13 - Jun 14
"Hina Hideaway", Views, AC, Walkable to Beach

Luxury Beachfront Condo with View

Luxury Beachfront Condo with View
Hauula
9.8 out of 10, Exceptional, (99 reviews)
"This place was absolutely perfect. It was so calm and peaceful very clean. Had all the amenities that I needed. The view and the location was awesome. Thank you for a wonderful stay. I will definitely be booking again."
United States
Zsalei A.
The price is CA $271
CA $899 total
includes taxes & fees
May 26 - May 27
Luxury Beachfront Condo with View

Beachfront Condo with Lanai and View

Beachfront Condo with Lanai and View
Hauula
10.0 out of 10, Exceptional, (3 reviews)
"Amazing location, had every amenity imaginable and so clean! "
United States
Jessica
The price is CA $453
CA $1,096 total
includes taxes & fees
Jun 14 - Jun 15
Beachfront Condo with Lanai and View

Comfy and Modern Condo By Waikiki

Comfy and Modern Condo By Waikiki
3.5 star property
Waikiki
The price is CA $164
CA $830 total
includes taxes & fees
Jun 8 - Jun 9
Comfy and Modern Condo By Waikiki

Aloha Suite Near the Sea III - 2 Block Walk to Beach!

Aloha Suite Near the Sea III - 2 Block Walk to Beach!
Waikiki
10.0 out of 10, Exceptional, (112 reviews)
"Host was very responsive and accommodating, the unit was clean and comfortable, and best of all the location has great access to the beach, restaurants, bus, and so forth. Would stay again!"
United States
Roy K.
The price is CA $97
CA $387 total
includes taxes & fees
May 26 - May 27
Aloha Suite Near the Sea III - 2 Block Walk to Beach!

Skyline Island Colony Hotel

Skyline Island Colony Hotel
3.0 star property
Waikiki
7.2 out of 10, Good, (2,250 reviews)
"Love the kitchenette and pool. Also amazing views of ocean, Diamondhead and the canal from the large lanai. Super awesome location as well. One of my favorite places to stay. I am a frequent local traveler. Its an older property but that doesn't bother me."
United States
Erin
The price is CA $161
CA $231 total
includes taxes & fees
Jun 7 - Jun 8
Skyline Island Colony Hotel

Waikiki renovated modern studio

Waikiki renovated modern studio
Waikiki
9.2 out of 10, Wonderful, (108 reviews)
"Host did a good job welcoming us. Room was nice, bed was comfortable. Meet our need."
United States
Jeremy H.
The price is CA $113
CA $288 total
includes taxes & fees
May 26 - May 27
Waikiki renovated modern studio

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

Cozy condo at Hawaiian monarch- free parking, no resort fee, near beaches, shop
Waikiki
9.8 out of 10, Exceptional, (34 reviews)
"Close to amenities, clean room. "
Canada
Michael
The price is CA $78
CA $397 total
includes taxes & fees
Jun 14 - Jun 15
Cozy condo at Hawaiian monarch- free parking, no resort fee, near beaches, shop

Ilikai Marina Vacations

Ilikai Marina Vacations
3.0 star property
Waikiki
8.4 out of 10, Very good, (43 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 CA $172
CA $492 total
includes taxes & fees
May 31 - Jun 1
Ilikai Marina Vacations

@ 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 CA $448
CA $774 total
includes taxes & fees
Jun 7 - Jun 8
@ Marbella Lane -coastal Retreat Near Diamond Head

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, (17 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 CA $136
CA $362 total
includes taxes & fees
Jun 9 - Jun 10
A Cozy and Romantic Studio at Heart of Waikiki

Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!

Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!
Waikiki
9.8 out of 10, Exceptional, (199 reviews)
"Clean room, nice kitchen, and complete supplies. Big bathroom."
United States
Peevee
The price is CA $97
CA $386 total
includes taxes & fees
May 27 - May 28
Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!

Marriott Vacation Club, Waikiki

Marriott Vacation Club, Waikiki
4.0 star property
Waikiki
9.6 out of 10, Exceptional, (165 reviews)
"Very friendly and fast check in/out."
United States
Norgy
The price is CA $452
CA $536 total
includes taxes & fees
May 25 - May 26
Marriott Vacation Club, Waikiki

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, (34 reviews)
"The property is so beautiful. I loved our stay. We stayed with 2 kids and it felt like home for us. Loved how accessible it is to beach. Not just beach but also to ala wai walking trail. With free parking this is a jackpot. So wonderful. I would definitely recommend this place to anyone."
United States
Amruthaa
The price is CA $221
CA $614 total
includes taxes & fees
May 25 - May 26
Partial Ocean View Condo with King or Queen Bed and Parking

Tropical Studios at Marine Surf Waikiki

Tropical Studios at Marine Surf Waikiki
3.0 star property
Waikiki
8.4 out of 10, Very good, (373 reviews)
"This Condo is the best and only place I will ever stay at when in Hawaii. 2 blocks from the beach, major shopping and resturants, and garage for my rental car, just perfect. "
United States
Danielle
The price is CA $153
CA $345 total
includes taxes & fees
Jun 1 - Jun 2
Tropical Studios at Marine Surf Waikiki

Waikiki Skyline 28th Floor Hawaiian Monarch

Waikiki Skyline 28th Floor Hawaiian Monarch
Waikiki
9.4 out of 10, Exceptional, (3 reviews)
"We absolutely loved our stay! The location was fantastic—we really enjoyed being right by the Ala Wai Canal. We also loved how close it was to a 7-Eleven and a great food truck spot, which made grabbing snacks and meals super convenient. We hadn’t realized there would be several parades and local events during our visit, which caused some road closures and traffic, but this property’s location made it easy for us to get in and out without any issues. I truly can’t recommend this stay enough. The...
United States
Joe A.
The price is CA $129
CA $375 total
includes taxes & fees
May 31 - Jun 1
Waikiki Skyline 28th Floor Hawaiian Monarch

Royal Kuhio

Royal Kuhio
3.5 star property
Waikiki
8.6 out of 10, Excellent, (578 reviews)
"Parking was easy and secure location was very central. Everything is within walking distance perfect location for families and couples. Definitely would recommend going there again in the future. Have stayed here multiple times."
United States
Wendy
The price is CA $248
CA $294 total
includes taxes & fees
May 24 - May 25
Royal Kuhio

Aston Waikiki Sunset

Aston Waikiki Sunset
4.0 star property
Waikiki
7.8 out of 10, Good, (3,198 reviews)
"We would definitely stay here again "
United States
Duane
The price is CA $247
CA $351 total
includes taxes & fees
May 28 - May 29
Aston Waikiki Sunset
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.

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?

BEST LOCATION , LANIKAI registration number W00530010-01 TMK 43005029 Licensed!: This Kailua vacation home rental is located in the mountains and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of books. 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 142 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.