Kailua Vacation Rentals

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Vacation Rentals in Kailua

Pool
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
10.0 out of 10, Exceptional, (3)
"My husband and I enjoyed six wonderful weeks in this house. From the moment we drove down that palm tree-lined road and stepped into the walled off courtyard, we knew we had picked the right place for our get-away. The house was tastefully and comfortably appointed. The kitchen, laundry room and bathrooms were all fully outfitted. We slept so well in the luxurious bedrooms, lulled by trade winds at night and waking to birds chirping in the morning. The outdoor lanai and backyard furniture made...
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
On the beach, beach towels
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
9.2 out of 10, Wonderful, (114)
"Great location."
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
Suite, 2 Bedrooms, Ocean View | In-room safe, desk, iron/ironing board, free cribs/infant beds
Aston Waikiki Sunset
4.0 star property
7.8 out of 10, Good, (2720)
"Overall everything was great. I gave it a 4 because we paid for the week of parking and 3/5 days they oversold the parking so we had to park and pay at the zoo. Also bigger vehicles not a good idea as we couldn’t park one of our vehicles here at all due to height. We know for next time to get a smaller car too. But we paid for 5 days of parking and 3/5 days ended up paying somewhere else for parking. Property also didn’t fill our soaps and towels fully each time so we had to ask for...
The price is $179
$253 total
includes taxes & fees
Jun 19 - Jun 20
Aston Waikiki Sunset
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Lobby sitting area
Kuhio Banyan Club
2.0 star property
6.8 out of 10, (1671)
"Very clean and quiet. Staff was helpful and great central location. Although an older building, filled with ohana love."
The price is $125
$189 total
includes taxes & fees
May 30 - May 31
Kuhio Banyan Club
Condo, 1 Bedroom, City View (Unit 55 ,1Bath) | Terrace/patio
Regency on Beachwalk Waikiki by OUTRIGGER
3.5 star property
8.0 out of 10, Very Good, (338)
"Jacques was amazing and so helpful!! Everyone who worked there was so friendly and helpful!! The outside of the hotel wasn’t impressive, but the room was really nice and updated. The full kitchen was awesome with so many appliances with the rice cooker and the blender. It was very comfortable and functional. Worked perfectly for me and my kids. "
The price is $195
$640 total
includes taxes & fees
Jun 15 - Jun 16
Regency on Beachwalk Waikiki by OUTRIGGER
Interior entrance
Aston at the Waikiki Banyan
3.0 star property
7.2 out of 10, Good, (2395)
"I had a room with a beautiful view and this place is a close walk to shops, food and beach"
The price is $179
$249 total
includes taxes & fees
May 30 - May 31
Aston at the Waikiki Banyan
View from property
Aston Waikiki Beach Tower
4.0 star property
9.2 out of 10, Wonderful, (1640)
"Amazing customer service and stunning views!! The staff went all out with extra perks for our family. Great location walking distance to everything!"
The price is $729
$914 total
includes taxes & fees
Jun 2 - Jun 3
Aston Waikiki Beach Tower
Beach nearby
Royal Kuhio
3.5 star property
8.6 out of 10, Excellent, (333)
"It was very clean and quiet!"
The price is $230
$271 total
includes taxes & fees
May 30 - May 31
Royal Kuhio
Studio, Ocean View (Unit #1305) | In-room safe, individually decorated, individually furnished
Waikiki Shore by OUTRIGGER
3.0 star property
8.0 out of 10, Very Good, (376)
"I was worried with some of the reviews I read so here’s my honest opinion. We’re a family of 6 (with older kids) staying for a week. It was very spacious, 2 full bathrooms and washer & dryer were a plus, loved the open kitchen and the beach view was the best! The beach was right there with easy access to it. We bought groceries and the fridge/freezer worked great. Appliances worked normal, there were pots & pans, most of what you’d expect in a kitchen. We cooked breakfast & lunches, bought out...
Waikiki Shore by OUTRIGGER
On the beach, sun loungers, beach umbrellas
Castle Waikīkī Shores
3.0 star property
8.2 out of 10, Very Good, (1108)
"The weather was bad most of the time, but it was a great stay!"
Castle Waikīkī Shores
Exterior
Hilton Grand Vacations Club at Hilton Hawaiian Village
4.0 star property
8.6 out of 10, Excellent, (699)
"Great amenities! Great service! Can’t wait to go back!"
The price is $319
$423 total
includes taxes & fees
Jun 2 - Jun 3
Hilton Grand Vacations Club at Hilton Hawaiian Village
Outdoor pool
Espacio The Jewel Of Waikiki
5.0 star property
9.8 out of 10, Exceptional, (14)
"Beautiful property and condo like accommodations with the floor all to ourselves. Highest level concierge services I have experienced with transportation services to and from airport included in stay. Will definitely be back! "
The price is $1,841
$2,171 total
includes taxes & fees
May 30 - May 31
Espacio The Jewel Of Waikiki
Exterior
Aqua Skyline at Island Colony
3.0 star property
7.2 out of 10, Good, (1913)
"Rooms need to be updated. Drapes were extremely past due to be replaced. Can’t beat the view of the ocean, canal & Diamond Head. Pool area and laundry were great. "
The price is $164
$224 total
includes taxes & fees
Jun 9 - Jun 10
Aqua Skyline at Island Colony
Beach nearby, white sand, sun loungers, beach umbrellas
Tropical Studios at Marine Surf Waikiki
3.0 star property
8.2 out of 10, Very Good, (291)
"Good location "
The price is $122
$262 total
includes taxes & fees
Jun 2 - Jun 3
Tropical Studios at Marine Surf Waikiki
Property grounds
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
9.6 out of 10, Exceptional, (109)
"We really enjoyed our visit to Hawaii and Michael’s property was perfect for us there was a strange smell from fridge which did linger on items we chilled so refrained from using but overall good and worked for us and our budget! Would stay again"
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
Pool
Clean studio in the heart of Waikiki!!
8.6 out of 10, Excellent, (22)
"Great spot for the price, perfect walking distance to pretty much everything. A ton of food trucks right across the street and just around the corner from some really cheap (for hawaii) bars. Will definitely be staying here again."
Clean studio in the heart of Waikiki!!
Studio | Pool
Spacious & Sophisticated Palms Studio Condo by RedAwning
3.0 star property
Spacious & Sophisticated Palms Studio Condo by RedAwning
Beach
Oceanside Estate - Spacious home with Pool & AC
10.0 out of 10, Exceptional, (1)
"We all enjoyed the property. It was a ways away from most activities but was quiet and we fit perfectly. The family all travel extensively and use B and B's and other means.. We did enjoy our stay and would recommend it."
Oceanside Estate - Spacious home with Pool & AC
Reception
Ala Moana Condo by Orgoto
3.5 star property
5.8 out of 10, (22)
"Air conditioning wasn’t working for first two days, room was moldy, hit and miss communication "
The price is $131
$383 total
includes taxes & fees
Jun 11 - Jun 12
Ala Moana Condo by Orgoto
View from property
Aloha Suite Near the Sea I, 3 min Walk to Beach! Great Location!
9.8 out of 10, Exceptional, (140)
"Peter was clear and prompt with communication. The location is perfect for the beach and restaurants."
The price is $74
$281 total
includes taxes & fees
Jun 3 - Jun 4
Aloha Suite Near the Sea I, 3 min Walk to Beach! Great Location!
Don't see what you're looking for?
See all available properties in Kailua
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.

Other types of properties in Kailua you may be interested in

Pool
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
10.0 out of 10, Exceptional, (3)
"My husband and I enjoyed six wonderful weeks in this house. From the moment we drove down that palm tree-lined road and stepped into the walled off courtyard, we knew we had picked the right place for our get-away. The house was tastefully and comfortably appointed. The kitchen, laundry room and bathrooms were all fully outfitted. We slept so well in the luxurious bedrooms, lulled by trade winds at night and waking to birds chirping in the morning. The outdoor lanai and backyard furniture made...
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
View from room
Hilton Hawaiian Village Waikiki Beach Resort
4.0 star property
8.2 out of 10, Very Good, (6531)
"Great location "
The price is $294
$406 total
includes taxes & fees
Jun 4 - Jun 5
Hilton Hawaiian Village Waikiki Beach Resort
On the beach, beach towels
Hyatt Regency Waikiki Beach Resort & Spa
4.0 star property
8.6 out of 10, Excellent, (3294)
"The beach is close and good quality The staff is kind and helpful The housekeeper is very good "
The price is $260
$365 total
includes taxes & fees
Jun 18 - Jun 19
Hyatt Regency Waikiki Beach Resort & Spa
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.

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Kailua in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $74 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!: This Kailua vacation home rental is located near the beach and has a balcony, a garden, and a barbecue grill 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. Make the most of the spa tub in this rental home to help you unwind. Another good choice for your trip to Kailua is BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY.

How many vacation rentals are there in Kailua?

With 181 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.

Recent reviews of Kailua properties
Expedia verified reviews

OUTRIGGER Waikiki Beach Resort

OUTRIGGER Waikiki Beach Resort

5/5 Excellent
"We had a perfect stay at Outrigger Waikiki Beach Resort. Very friendly and welcoming staff, clean, super convenient and perfect access to beach ,shops ,and activities.Highly recommended! "
A verified traveler stayed at OUTRIGGER Waikiki Beach Resort
Posted 9 hours ago
OUTRIGGER Waikiki Beach Resort