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Compare 362 Vacation Homes in Kailua with updated reviews, rates, and availability.

Aloha Adventure Home - 2 min from beach

9.2 out of 10, Wonderful, (21)
"Good location, n"
Aloha Adventure Home - 2 min from beach

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.

10.0 out of 10, Exceptional, (27)
"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.

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

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

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

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!

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!

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

8.8 out of 10, Excellent, (55)
"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

Impeccable Penthouse - Ocean & Diamondhead Views

9.8 out of 10, Exceptional, (160)
"Cozy and clean, can’t beat the view and location. Jan was a great communicator and her listing is accurate. We’ve stayed in various Waikiki locations and this was ideal for us. If you plan to rent a parking space, a mid-size SUV is the largest you should get. "
Impeccable Penthouse - Ocean & Diamondhead Views

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

9.0 out of 10, Wonderful, (126)
"Host was excellent with responses and clearly conveying expectations. Property was very pretty and along the beach access our daughter normally uses to get to the beach. Kitchen well accessorized with cooking needs, spices, etc. Our space was shared by family of 2 older adults and 2 younger adults. Stayed for a week of enjoyment, both before and after the wedding. "
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

Absolutely Oceanfront - 60' Waterfall Lap Pool

9.4 out of 10, Exceptional, (154)
"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

Ocean View Escape - Gorgeous ocean views, AC

Perfect Location on Kailua Beach - Licensed Short Term Rental

9.6 out of 10, Exceptional, (121)
"The beach home is absolutely lovely and embraces all that is Hawaii - relaxed, soothing, sunshine, fun, and the aloha spirit. Being in Kailua was also great as its close to all the services needed. Kailua also has a great island vibe."
Perfect Location on Kailua Beach - Licensed Short Term Rental

Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale

9.6 out of 10, Exceptional, (38)
"Loved the location. Walk to beach and pull box hike. The pool was lovely! Enjoyed the hammock. It was clean, felt safe and secure. Keyless lock was really covenant. Would book again and highly recommend to others. "
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale

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!

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!

Garden Hotel in Central Waikiki

Garden Hotel in Central Waikiki

Makana Dream - Beachfront

8.8 out of 10, Excellent, (10)
"Upon walking in someone said it’s like being on a boat. The expansive windows make you almost feel you’re in the water. Peaceful and quiet except for the sound of waves. Close to everything you need including the Breath of life show at the PCC across the street. The view of the mountains and sky was magnificent. Crab catching (and releasing) plus turtle watching at night. Loved our time there. "
Makana Dream - Beachfront

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

10.0 out of 10, Exceptional, (32)
"Kameron was such an excellent host! Instructions were clear and everything went so smooth. The unit was clean and had everything we could possibly need for our stay, including boogie boards, umbrellas, and chairs. We were celebrating my birthday and he went out of his way to provide a cake and lei. He allowed us an early check in and late check out. We will definitely choose one of his properties in the future. Also, the views from this unit were incredible! The central air was a very nice touch...
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
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

9.0 out of 10, Wonderful, (126)
"Host was excellent with responses and clearly conveying expectations. Property was very pretty and along the beach access our daughter normally uses to get to the beach. Kitchen well accessorized with cooking needs, spices, etc. Our space was shared by family of 2 older adults and 2 younger adults. Stayed for a week of enjoyment, both before and after the wedding. "
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

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

4.0 star property
7.8 out of 10, Good, (2865)
"Liked the ocean view, kitchen was nice but frying pan was terrible."
The price is SAR 572
SAR 830 total
includes taxes & fees
28 Jan - 29 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.