Holiday Homes in Kailua

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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Holiday Homes in Kailua and around

Makana Dream - Beachfront
Experience the serene coastal town with a long stretch of sandy beach and breathtaking ocean views.

Makana Dream - Beachfront

9.0 out of 10, Wonderful, (17)
"The best part of our stay was that the location was close to everything that we had planned to do. There was a hiccup with check in as they had changed the codes on the doors and didn't let us know about it a head of time. We didn't have to wait long and we were able to get the correct codes. We loved our stay at this property."
Makana Dream - Beachfront
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
Enjoy serene beach views and scenic islands from this tranquil beachside location.

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

9.2 out of 10, Wonderful, (136)
"Our family enjoyed our stay at this lovely home. The location was perfect and the beach was fantastic. So nice to spend some time relaxing here. "
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
Manoa Valley A 2BR with ocean and mountain views
Kitchen with central island, sink, and ample countertop space, featuring a refrigerator, oven, and glass-fronted cabinetry.

Manoa Valley A 2BR with ocean and mountain views

9.8 out of 10, Exceptional, (52)
"Visited with a group of 4 adults and we each had our own space which was lovely. House is very conveniently located to easily access everywhere we wanted to visit on the island. The house is charming and has a stunning view of the Waikiki shore. Would absolutely stay here again for a future visit!"
Manoa Valley A 2BR with ocean and mountain views
Garden Hotel in Central Waikiki
Enjoy the tropical view from your balcony, featuring a pool table and comfortable seating for two.

Garden Hotel in Central Waikiki

2.0 out of 10, (2)
"When I booked the room it said there were 2 beds and two baths. Upon arrival the units are all 1 bed 1 bath. This caused a problem. I have a text message showing 2 bed 2 bath."
Garden Hotel in Central Waikiki
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!
Enjoy stunning ocean views from the comfort of this beachfront resort, featuring a pool area with umbrellas and sun loungers.

Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!

9.8 out of 10, Exceptional, (116)
"Great location. Awesome place!"
The price is €696
includes taxes & fees
16 Aug - 17 Aug
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!
Enjoy panoramic ocean and mountain views from this beachfront hotel's high-rise buildings.

Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!

9.6 out of 10, Exceptional, (59)
"My family enjoyed the impressive spot on Waikiki. Comfortable accommodations and great food options nearby. Thanks for the wonderful stay."
The price is €1,045
includes taxes & fees
20 Jul - 21 Jul
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
Enjoy meals in the spacious kitchen with a large island and sink, and dine with a scenic view of the mountains.

Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range

10.0 out of 10, Exceptional, (47)
"Great proximity to Waikiki beach and beautiful views. "
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
New Aloha Waikiki Ilikai Hotel Condo Free Parking
Beach nearby

New Aloha Waikiki Ilikai Hotel Condo Free Parking

10.0 out of 10, Exceptional, (32)
"Our stay was great. The location and parking spot was perfect for us to be able to rent a car and get around all of Oahu during our stay, but was also walking distance to restaurants and shopping in Waikiki. Everything was well stocked with towels, essentials and beach gear. Thank you for a wonderful stay!"
New Aloha Waikiki Ilikai Hotel Condo Free Parking
Nani Iki - Close to beach!
Relax in this inviting living area with a sofa, armchairs, and dining space.

Nani Iki - Close to beach!

10.0 out of 10, Exceptional, (14)
"Great property, bed was comfy, nice showers and right by the ocean. Family loved it. "
Nani Iki - Close to beach!
Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!
Relax by the serene pool surrounded by lush tropical vegetation and shaded by palm trees.

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

9.6 out of 10, Exceptional, (199)
"Our stay was wonderful. The location was perfect. Nice amenities and kitchen/bathrooms had xtra supplies needed for our stay. Truly a gem in Kailua. Easy access to the beach and stores. The owners were easy to connnect with and a cute folder with instructions and recommendations were provided. We will be back. Thank you "
Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!
Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views
Relax in this stylish living room with a comfortable sofa, flat-screen TV, and a beautiful mountain view.

Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views

10.0 out of 10, Exceptional, (59)
"This property was very close to the beach and walking distance to great restaurants. Plenty of space for everyone to unwind from a day soaking up the sun. And the view of Diamond Head is outstanding!"
Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views
Oceanfront Romantic Couple's Getaway with Private Beach w/ Full Living Amenities
Enjoy breathtaking ocean views from this balcony with a table and two chairs.

Oceanfront Romantic Couple's Getaway with Private Beach w/ Full Living Amenities

9.4 out of 10, Exceptional, (81)
"Listing is accurate. Right on beach, peaceful, simple accommodations. "
Oceanfront Romantic Couple's Getaway with Private Beach w/ Full Living Amenities
Hale Koolau 2-bedroom house with WiFi, W/D and AC in lovely Kaneohe 30days
Walk along the beach, surrounded by lush greenery and palm trees, with the majestic mountain range in the distance.

Hale Koolau 2-bedroom house with WiFi, W/D and AC in lovely Kaneohe 30days

Hale Koolau 2-bedroom house with WiFi, W/D and AC in lovely Kaneohe 30days
Oahu Paradise - AC, 1 block to beach!
Enjoy a serene beach experience with turquoise waters gently lapping onto the sandy shore, surrounded by lush green trees.

Oahu Paradise - AC, 1 block to beach!

8.4 out of 10, Very good, (13)
"We were very glad that the property was close to things we wanted to participate in. The property was very clean. Thanks"
Oahu Paradise - AC, 1 block to beach!
Pono Pearl Villa | Beach Access + AC In Every Room
Enjoy a serene beach experience with gentle waves lapping onto the shore.

Pono Pearl Villa | Beach Access + AC In Every Room

10.0 out of 10, Exceptional, (30)
"Just spent a week, and it was AMAZING… ocean was literally across the street! Would highly recommend!"
Pono Pearl Villa | Beach Access + AC In Every Room
LUANA WAIKIKI HOTEL 502 🏝 2 Queen Bed CityViewStudio,WiFi,AC,GYM,POOL & Kitchen
Relax on the balcony with a view of the city's diverse skyline.

LUANA WAIKIKI HOTEL 502 🏝 2 Queen Bed CityViewStudio,WiFi,AC,GYM,POOL & Kitchen

LUANA WAIKIKI HOTEL 502 🏝 2 Queen Bed CityViewStudio,WiFi,AC,GYM,POOL & Kitchen
Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach
Overlooking the ocean, this beachfront neighborhood offers stunning views of the coastline and lush greenery.

Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach

10.0 out of 10, Exceptional, (32)
"We LOVED"
Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach
Mea Kanu Paradise, Beach Access, A/C, Sleeps 6
Enjoy stunning ocean views from this beachfront property surrounded by lush greenery and palm trees.

Mea Kanu Paradise, Beach Access, A/C, Sleeps 6

9.8 out of 10, Exceptional, (38)
"Clean and nicely updated beach rental. Nicely located on north shore. Close to lots of beautiful beaches and fun attractions. Mahalo "
Mea Kanu Paradise, Beach Access, A/C, Sleeps 6
Marina front, private pool AND A/C! Available for Spring Break!
Enjoy cooking in this well-equipped kitchen with a stainless steel sink, microwave, and coffee maker.

Marina front, private pool AND A/C! Available for Spring Break!

8.8 out of 10, Excellent, (64)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: House had plenty of room and was well equipped. Amanda was an excellent host that took care of everything super quickly when something came up. Location is wonderful and close to grocery stores and dining. A few things need updating but we...
Marina front, private pool AND A/C! Available for Spring Break!
Kailua Oceanfront Villa with Heated Pool & Spa
Relax in a spacious room with a panoramic ocean view, featuring a comfortable seating area with a sofa, coffee table, and chairs.

Kailua Oceanfront Villa with Heated Pool & Spa

10.0 out of 10, Exceptional, (110)
"Richard’s home is an amazing retreat to paradise. Our family could not have enjoyed the experience more.The home is laid out spaciously with many areas to spread out and enjoy the sights and sounds of the surf and ocean.The support once on site was immediate and gracious.The pictures are beautiful but the in person experience is far better.We hope to return again soon."
Kailua Oceanfront Villa with Heated Pool & 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.
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Top Kailua Hotel Reviews

Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

10/10 Excellent
"Very open and close to all stores and restaurants. It’s a beautiful hotel . Also close by the beach . Nice pools "
Monica 4-night trip
Posted 13 hours ago
Sheraton Waikiki Beach Resort