Kailua Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Kailua Vacation Homes

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

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

9.6 out of 10, Exceptional, (202)
"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!
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
Interior

Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.

10.0 out of 10, Exceptional, (72)
"The house, location, amenities made this home a home away from home. The backyard is a family oasis for all ages and enough space to have some quiet time if needed. We hope to visit again soon!"
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
Garden Hotel in Central Waikiki
Interior

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!
On the beach

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 CA $412
CA $1,080 total
includes taxes & fees
Aug 16 - Aug 17
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
Fridge, microwave, oven, stovetop

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
The Best View in Waikiki, only steps away from the best beach in the world
On the beach, sun loungers, beach towels

The Best View in Waikiki, only steps away from the best beach in the world

9.8 out of 10, Exceptional, (136)
"Great location to walk around the waikiki area"
The Best View in Waikiki, only steps away from the best beach in the world
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
On the beach, beach towels

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
Pono Pearl Villa | Beach Access + AC In Every Room
Beach nearby

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
Viewhouse in Lanikai BEST LOCATION , LANIKAI NUC 90/BB -0108
Interior

Viewhouse in Lanikai BEST LOCATION , LANIKAI NUC 90/BB -0108

9.6 out of 10, Exceptional, (73)
"Would definitely stay here again. Mahalo to owners."
Viewhouse in Lanikai BEST LOCATION , LANIKAI NUC 90/BB -0108
Oceanfront Romantic Couple's Getaway with Private Beach w/ Full Living Amenities
Property grounds

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
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!
On the beach, sun loungers, beach towels

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 CA $274
CA $899 total
includes taxes & fees
Aug 14 - Aug 15
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!
LUANA WAIKIKI HOTEL 502 🏝 2 Queen Bed CityViewStudio,WiFi,AC,GYM,POOL & Kitchen
Property grounds

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
Beach nearby, sun loungers

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
Marina front, private pool AND A/C! Available for Spring Break!
Fridge, microwave, oven, stovetop

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!
Impeccable Penthouse - Ocean & Diamondhead Views
Property grounds

Impeccable Penthouse - Ocean & Diamondhead Views

9.8 out of 10, Exceptional, (172)
"We loved staying at this beautiful property. Jan is a fantastic communicator. Everything was as discribed. Room was clean, and came equipped with everything you need for a stay on Oahu. Views were fantastic. Great location, easy access to many great beaches, activities, and shopping. Would definitely stay here again."
Impeccable Penthouse - Ocean & Diamondhead Views
Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views
Smart TV

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
Kailua Oceanfront Villa with Heated Pool & Spa - SEPTEMBER now available!
Interior

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

☀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
Absolutely Oceanfront - 60' Waterfall Lap Pool
Exterior

Absolutely Oceanfront - 60' Waterfall Lap Pool

9.4 out of 10, Exceptional, (161)
"We wanted an Oahu vacation without Waikiki craziness, and found it here. Great neighborhood, easy in and out to see the sights. "
Absolutely Oceanfront - 60' Waterfall Lap Pool
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kailua Hotel Reviews

Prince Waikiki

Prince Waikiki

10/10 Excellent
"Amazing stay! I will be back for sure!"
Jamal 5-night trip
Posted 5 hours ago
Prince Waikiki