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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 340 Vacation Homes in Kailua with updated reviews, rates, and availability.

Viewhouse in Lanikai BEST LOCATION , LANIKAI NUC 90/BB -0108
May photo is from level 2. Level 1 has more foliage but ocean can still be seen

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

9.6 out of 10, Exceptional, (65)
"Perfect location for a great beach trip"
Viewhouse in Lanikai BEST LOCATION , LANIKAI NUC 90/BB -0108
Just a couple houses away from the nicest beach on the island.
Sunrise on the Beach

Just a couple houses away from the nicest beach on the island.

10.0 out of 10, Exceptional, (28)
"I have stayed in this neighborhood before in different rental properties and this was by far the nicest place with the most privacy. Excellent location, quiet neighborhood, proximity to beach is wonderful. House is great, patio was a wonderful bonus with lots of privacy."
Just a couple houses away from the nicest beach on the island.
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
Living area

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

10.0 out of 10, Exceptional, (33)
"The Positives:- Pictures were accurate- Clean Unit- Free Parking is clutch- Excellent location (short walk to international marketplace / target / Beach)- Bed was comfortable- Stocked with Beach equipment! (Lounge Chairs, Beach towels, boogie boards, umbrellasAreas for improvement:- The Unit is located within a very outdated hotel (Aston Waikiki). The Elevators need renovation. Although there are 4 elevators, it often felt like only 1 was in use at a time. People would often crowd into the...
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
Ocean Front Center of Kailua Bay! Best Location!!

Ocean Front Center of Kailua Bay! Best Location!!

10.0 out of 10, Exceptional, (29)
"Best place for families, our whole family enjoyed our time together in this great place!"
Ocean Front Center of Kailua Bay! Best Location!!
House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more
There are 4 houses on this side. Next house not unitl the point in the distance

House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more

9.2 out of 10, Wonderful, (85)
"Convenient location 3 mins walk from the ocean. The house has surfs, kayaks and boogies. "
House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more
Charming Country Hale,ParkingWi-Fi,30 Night Rental
Our favorite beach to swim and boogie board, called Kekela or Kolololio Beach.

Charming Country Hale,ParkingWi-Fi,30 Night Rental

9.8 out of 10, Exceptional, (94)
"Just the perfect little house to get away from the hustle and bustle of the east side of the island. Such a little gem of a place. Excellent hosts!"
Charming Country Hale,ParkingWi-Fi,30 Night Rental
Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach
Terrace/patio

Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach

9.6 out of 10, Exceptional, (187)
"Parking tight, mobility tough for handicapped, second bathroom outside, downstairs. Unit could use some TLC. Nice, comfortable furniture & beds. TV on Roku, remote gave us problems, freezer didn’t make ice cubes."
Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach
Welcome to Ho'onani Pua Hale
Living area

Welcome to Ho'onani Pua Hale

9.8 out of 10, Exceptional, (10)
"Cant say anything but wat a wonderful stay at the house very beautiful clean and very easy to check out will stay again for sure thank u"
Welcome to Ho'onani Pua Hale
Beachfront Private, N. Shore & Legal Vacation!
Beach

Beachfront Private, N. Shore & Legal Vacation!

10.0 out of 10, Exceptional, (2)
"This place is in the most beautiful location. It is right on the beach and most of the time we had that beach to ourselves. The home, as clearly stated in the description, is older and worn but has a lot of charm and plenty of room for our family of eight adults. Since 11 people are actually allowed to stay there it would be handy to have some fold up chairs for the dining room table but for us it was perfect.! Overall it was the most wonderful place to celebrate our 50th wedding anniversary...
Beachfront Private, N. Shore & Legal Vacation!
Garden Hotel in Central Waikiki
Outdoor dining

Garden Hotel in Central Waikiki

Garden Hotel in Central Waikiki
Magic North Shore Beach House 30 day rental PCC BYU
Exterior

Magic North Shore Beach House 30 day rental PCC BYU

9.6 out of 10, Exceptional, (13)
"Great spot in close proximity to everything we wanted to do. "
Magic North Shore Beach House 30 day rental PCC BYU
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
Beach

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

9.0 out of 10, Wonderful, (126)
"We are a family of 6, all adults and loved staying here. Beautiful place with lots of space to relax and enjoy Hawaii life. HIGHLY recommend! Our host, Crystal"
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
Absolutely Oceanfront - 60' Waterfall Lap Pool
Ocean Front Home with Pool

Absolutely Oceanfront - 60' Waterfall Lap Pool

9.4 out of 10, Exceptional, (155)
"We had the most incredible stay at this property! The location is truly unmatched—practically sitting right on the ocean, with the sound of waves crashing against the lava stones as a constant, soothing backdrop. Waking up to the sound of the surf and enjoying our morning coffee while watching the waves was an experience we’ll never forget.The home was clean, comfortable, and well-equipped with everything we needed for a relaxing getaway. If you're looking for a peaceful, oceanfront retreat...
Absolutely Oceanfront - 60' Waterfall Lap Pool
Ocean View Escape - Gorgeous ocean views, AC
Aerial view

Ocean View Escape - Gorgeous ocean views, AC

10.0 out of 10, Exceptional, (1)
Ocean View Escape - Gorgeous ocean views, AC
White Hibiscus B -home on Laie Point, Beach access
White Hibiscus Estate is a 4-bedroom home with incredible views.Views are what capture your eye in this full room view. Doors open to unobstructed views.

White Hibiscus B -home on Laie Point, Beach access

10.0 out of 10, Exceptional, (1)
"We traveled as a group of 15, four families, for ten days in Laie point. The house was so great, room for kids to play, adults played cards, and room for large group meals. Each bedroom had a bathroom with shower for each family to retreat to during the day. The view is unbelievable and the semiprivate beach was so special. No one wanted to leave as it was such a special experience."
White Hibiscus B -home on Laie Point, Beach access
Amazing beach house with gorgeous views of the sunrise!
Exterior

Amazing beach house with gorgeous views of the sunrise!

10.0 out of 10, Exceptional, (21)
"This property is beautiful! Shannon the property owner is responsive and kind. The proximity to the beach without the hustle and bustle of the other side of island was our favorite. We stayed 4 adults a toddler and a baby. Would definitely stay again"
Amazing beach house with gorgeous views of the sunrise!
Kailua Beachside, 2 Houses off beach, 2bed/2bath, Sleeps 8, Ocean & Mtn Views
View to the left from the Beach Access

Kailua Beachside, 2 Houses off beach, 2bed/2bath, Sleeps 8, Ocean & Mtn Views

8.8 out of 10, Excellent, (56)
"It was great to get away from the crowd and relax after running the marathon "
Kailua Beachside, 2 Houses off beach, 2bed/2bath, Sleeps 8, Ocean & Mtn Views
30 day Perfect “BEACHFRONT “ Getaway! Steps to the beach through the backyard
Dining

30 day Perfect “BEACHFRONT “ Getaway! Steps to the beach through the backyard

9.6 out of 10, Exceptional, (34)
"My wife and I were just married 11/24/23 and this was our first trip as 1 big family. Combined we had 4 daughters, 1 son, 1 son in law, 3 grandsons and 1 possible daughter in law. The home was big enough for us all comfortably. The beach was amazing. It’s not a private beach but it might as well have been!!! Truly a perfect trip."
30 day Perfect “BEACHFRONT “ Getaway! Steps to the beach through the backyard
Marina front, private pool AND A/C! BOOK NOW!

Marina front, private pool AND A/C! BOOK NOW!

8.8 out of 10, Excellent, (63)
"Super convenient location for our activities. Our family enjoys a slower paced HI vacation visiting family and our usual hot spots. This home has plenty of space and loved sitting outside each day watching the water and drinking our coffee. The home is older, but very comfortable and clean. Thanks to to super responsive hosts who were always quick to reply!!!"
Marina front, private pool AND A/C! BOOK NOW!
Most Contemporary Estate in the heart of Honolulu-Luxury Living .
Exterior

Most Contemporary Estate in the heart of Honolulu-Luxury Living .

10.0 out of 10, Exceptional, (21)
"Great view, large space, awesome place to stay."
The price is AED 6,244
AED 12,153 total
includes taxes & fees
22 Jan - 23 Jan
Most Contemporary Estate in the heart of Honolulu-Luxury Living .
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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Other property types in Kailua

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

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

9.0 out of 10, Wonderful, (126)
"We are a family of 6, all adults and loved staying here. Beautiful place with lots of space to relax and enjoy Hawaii life. HIGHLY recommend! Our host, Crystal"
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
Private Beachfront Rental
Property grounds

Private Beachfront Rental

9.8 out of 10, Exceptional, (218)
"Shari is fantastic and the unit's location was equally fantastic. Will return in the future."
Private Beachfront Rental
Aston Waikiki Sunset
Exterior

Aston Waikiki Sunset

4.0 star property
7.8 out of 10, Good, (2866)
"Liked the ocean view, kitchen was nice but frying pan was terrible."
The price is AED 576
AED 831 total
includes taxes & fees
25 Jan - 26 Jan
Aston Waikiki Sunset
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.