Holiday Homes in Kailua

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Kailua and around

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, (137)
"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, (54)
"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, (117)
"Beautiful place to stay. As a family of seven it accommodated us comfortably. We also appreciated the little extras like the beach chairs and boogie boards. The view was amazing and we spent a lot of time out on the balcony. "
The price is €693
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 €577
includes taxes & fees
14 Aug - 15 Aug
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, (50)
"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, (33)
"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
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, (200)
"The location was excellent and the unit was comfortable. We were disappointed as five adults to find that there were not really enough beds to accommodate us. One double bed, two singles, and sheets to cover a couch. Enjoyed our stay. "
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)
"Excellent communication, easy check-in, remodeled unit, convenient parking, clean, well furnished condo."
Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views
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
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
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)
"Our stay (6 adults, some working some on vacay) was really nice. Clean and spacious, good location, responsive caretaker. The beach is easy to access. Would choose this stay again."
Pono Pearl Villa | Beach Access + AC In Every Room
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, (15)
"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!
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

6.0 out of 10, (1)
"Great unit, as described…once it was cleaned and ready for check in the day following our scheduled arrival. "
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, (39)
"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 - SEPTEMBER now available!
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 - SEPTEMBER now available!

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 - SEPTEMBER now available!
"Pineapple Perch" | Fully Renovated | A/C in Every Room
Enjoy cooking in this well-lit kitchen with a central island and oven.

"Pineapple Perch" | Fully Renovated | A/C in Every Room

9.6 out of 10, Exceptional, (10)
"We had a great stay on the north shore and the house was a great home base for exploring. Thanks for including things like boogie and paddleboards, coolers, and chairs. it made everything so easy."
"Pineapple Perch" | Fully Renovated | A/C in Every Room
☀Waikiki Grand Hotel® 214-2025 Remodel Energetic Queen Studio w/Lanai sleeps 2
Enjoy the ocean view from this balcony with comfortable seating and a railing overlooking the beach.

☀Waikiki Grand Hotel® 214-2025 Remodel Energetic Queen Studio w/Lanai sleeps 2

6.0 out of 10, (1)
"The room was cleanish, the floors weren't the best. The room definitely showed it's age, except for the kitchenette and fridge. The window a/c was on the floor blowing against the bathroom door and the kitchen cabinet. So you really had to crank it up to get the room to cool down. My main complaint is for the noise. The room is on the second floor, and the doors to the patio are old. So ALL street noise, at all hours comes in. Also, the door to the room that leads to the hotel hallway is 20ft...
☀Waikiki Grand Hotel® 214-2025 Remodel Energetic Queen Studio w/Lanai sleeps 2
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

Ramada Plaza by Wyndham Waikiki

Ramada Plaza by Wyndham Waikiki

10/10 Excellent
"Nice and clean small hotel with friendly staffs. Location is excellent to the beach and shopping. We would stay here again if we travel to Waikiki"
Minh 3-night trip
Posted 7 hours ago
Ramada Plaza by Wyndham Waikiki