Kailua Holiday Rentals

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Holiday 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!
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
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 NZ$3,852
includes taxes & fees
4 Jun - 5 Jun
Espacio The Jewel Of Waikiki
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View from property
Aloha Suite Near the Sea I, 3 min Walk to Beach! Great Location!
9.8 out of 10, Exceptional, (137)
"Nice clean room, water off one day but not host problem. Nice safe entry with security present. Secure elevator and room. Room very clean and everything we needed to make our stay wonderful."
The price is NZ$473
includes taxes & fees
21 May - 22 May
Aloha Suite Near the Sea I, 3 min Walk to Beach! Great Location!
Beach
Waikiki Beach ocean view studio with pool access right on the white sand beach.
9.8 out of 10, Exceptional, (147)
"We spent nearly a week in Waikiki and were grateful for the location and proximity of this condo to the beach, restaurants, shopping, and much more. The unit itself could use some updating but the views from the balcony were perfect and the in-unit laundry was extremely convenient. There was also minimal noise which was nice given the bustling location. Pros: - Location - Balcony Views - In-Unit Laundry - Kitchen - Comfortable Bed - Owner was extremely responsive Cons: - Unit could use some...
The price is NZ$1,183
includes taxes & fees
19 May - 20 May
Waikiki Beach ocean view studio with pool access right on the white sand beach.
Property grounds
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
9.6 out of 10, Exceptional, (108)
"Mike’s place was perfect! Clean, comfortable, and well appointed. He had starters for coffee, hair dryer, a beach chair and cooler and even an umbrella. Location is great - quick walk to beach, restaurants, shopping. Pool and surrounding deck was clean and very nice. Great host- I hope to stay again during my next visit to Honolulu. Mahalo Mike."
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
Beach nearby, sun-loungers, beach towels
Aloha Suite Near the Sea II, 3 Min Walk to Beach
9.6 out of 10, Exceptional, (108)
"Amazing location to everything! Clean and in safe location "
The price is NZ$568
includes taxes & fees
4 Jun - 5 Jun
Aloha Suite Near the Sea II, 3 Min Walk to Beach
On the beach, beach towels
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
9.2 out of 10, Wonderful, (113)
"Family from New England visiting my family who lives in the north shore of Oahu. Perfect location."
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
View from property
Aston Waikiki Beach Tower
4.0 star property
9.2 out of 10, Wonderful, (1635)
"The front desk is so great!!!!"
The price is NZ$1,338
includes taxes & fees
19 May - 20 May
Aston Waikiki Beach Tower
Interior
Heart of Downtown Honolulu
9.2 out of 10, Wonderful, (41)
"its a great location to stay, reasonable price, and free parking. perfect for a big family."
Heart of Downtown Honolulu
Sun-loungers, beach towels
Ocean view in Waikiki, Free Parking stall. Hawaiian dream vacation Free Wifi &AC
9.2 out of 10, Wonderful, (27)
"This property is ideally located for shopping, eating, and site seeing. We discovered several tourist tour pick up location was a the Ross store across the street. The restaurant downtown is amazingly delicious! The property balconies are wonderful for morning coffee and just relaxing in the Hawaiian air. There was plenty of space for my husband and I to enjoyed being in the space, it is inviting, comfortable, and offers all the amenities we were looking for during our stay Ms. Orly is a...
The price is NZ$800
includes taxes & fees
29 May - 30 May
Ocean view in Waikiki, Free Parking stall. Hawaiian dream vacation Free Wifi &AC
Studio | Pool
Kuhio Village 904a Condo by RedAwning
3.0 star property
9.0 out of 10, Wonderful, (2)
Kuhio Village 904a Condo by RedAwning
Beautiful Pent House, Super nice $60!
8.8 out of 10, Excellent, (32)
"The location was brilliant just around the corner from Star Beachboys surfboard hire and 2 short blocks from the main beach (Canoes- where the Duke Kahanamoku statue is). We had some problems accessing our key from the lockbox- you need to pull out or up on the grey tab- and getting in the apt door- turn the key right and then fully left. But there was a 24 hour security desk to get help. The building and elevator were a bit tired (the apt is 12 stories up on the top floor). The bed was a queen...
Beautiful Pent House, Super nice $60!
Beach nearby
Royal Kuhio
3.5 star property
8.6 out of 10, Excellent, (330)
"I liked pretty much the whole experience of staying at this property."
The price is NZ$443
includes taxes & fees
19 May - 20 May
Royal Kuhio
Front of property - evening/night
Hilton Grand Vacations Club at Hilton Hawaiian Village
4.0 star property
8.6 out of 10, Excellent, (690)
"We had an amazing time. We will book again in the future"
The price is NZ$730
includes taxes & fees
7 Jun - 8 Jun
Hilton Grand Vacations Club at Hilton Hawaiian Village
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!!
Exterior
King Bed Suite at The Waikiki Grand - Just steps away from Waikiki Beach
8.6 out of 10, Excellent, (18)
"This room was nice, and located near the beach, zoo, park, and aquarium. I had a blast and was away from the room most of the time. I slept great and the sun deck is great during sunrise. Thank You!"
King Bed Suite at The Waikiki Grand - Just steps away from Waikiki Beach
Deluxe Suite, 2 Bedrooms, Beach View | Private kitchen
Castle Waikīkī Shores
3.0 star property
8.2 out of 10, Very good, (1104)
"The beach is right outside the back door, with amazing views and friendly employees. Everything is within walking distance from the hotel. "
Castle Waikīkī Shores
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 NZ$428
includes taxes & fees
18 May - 19 May
Tropical Studios at Marine Surf Waikiki
Corner Unit Studio@Waikiki Hotel Building 1 day min
8.2 out of 10, Very good, (63)
"Perfect location! The wind is a little loud in early February but otherwise was perfectly well appointed and comfortable for my husband and I asked our co-sleeping toddler!"
The price is NZ$378
includes taxes & fees
10 Jun - 11 Jun
Corner Unit Studio@Waikiki Hotel Building 1 day min
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!
On the beach, beach towels
Hyatt Regency Waikiki Beach Resort & Spa
4.0 star property
8.6 out of 10, Excellent, (3259)
"Overall was quite nice. The only thing was a lack of dining facilities in the hotel. "
The price is NZ$578
includes taxes & fees
16 Jun - 17 Jun
Hyatt Regency Waikiki Beach Resort & Spa
View from room
Hilton Hawaiian Village Waikiki Beach Resort
4.0 star property
8.2 out of 10, Very good, (6470)
"Property is right on the beach. Multiple restaurants. Shopping right there. Two different Luaus on property and fireworks every Friday night."
The price is NZ$629
includes taxes & fees
1 Jun - 2 Jun
Hilton Hawaiian Village Waikiki Beach Resort
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kailua holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Kailua. 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 Kailua. 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 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 holiday 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 Kailua short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Kailua?

Yes, there are holiday rentals close to the most popular sights in Kailua, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the popular beaches in Kailua.

How many holiday rentals are there in Kailua?

With 184 Expedia holiday rentals, you're guaranteed to find just the right place for your Kailua stay.

What’s there to see and do in Kailua?

Kailua Bay Beach and Kailua Beach are a couple of lovely local spots to get outside and enjoy nature. You’ll find favourite places to visit such as Ala Moana Center and Waikiki Beach Walk in the wider area.

What’s a holiday rental in Kailua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kailua. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.

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