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Search results; Over 1,000 homes in Kailua

Top guest favorite
This beachfront Lanikai treehouse puts you 100 yards from the ocean
1 bedroom, 1 bed, 1 private bath
Sep 4 – 11
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5.0 out of 5 average rating, 29 reviews
Guest favorite
This Lanikai house puts you across the street from the beach with a tiki bar backyard
4.9 out of 5 average rating, 50 reviews, 4 bedrooms, 5 beds, 3 baths
Sep 2 – 7
Top guest favorite
This Kailua guesthouse puts you an 8-minute walk from the beach, with a private lanai
4.87 out of 5 average rating, 459 reviews, 1 bedroom, 2 beds, 1 bath
Sep 16 – 21
Top guest favorite
This Kailua retreat gives you kayaks, paddleboards, and a 6-minute walk to the beach
4.96 out of 5 average rating, 131 reviews, 1 bedroom, 2 beds, 1 bath
Aug 24 – 29
Top guest favorite
This Lanikai studio puts you 100 yards from the beach through a private garden gate
5.0 out of 5 average rating, 28 reviews, 1 bed, 1 bath
Sep 10 – 15
Guest favorite
This renovated beachfront Kailua estate gives you a private lawn and separate cottage
5.0 out of 5 average rating, 10 reviews, 6 bedrooms, 7 beds, 4 baths
Sep 2 – 7
Superhost
This Kailua tiny house gives you a camping experience on Oahu
1 bedroom, 1 bed, Half-bath
Aug 28 – Sep 2
Guest favorite
Soak in the lagoon-style pool at this gated Kailua home near the beach
5.0 out of 5 average rating, 13 reviews, 6 bedrooms, 12 beds, 5.5 baths
Nov 28 – Dec 5
Guest favorite
Wake to turquoise waters at this beachfront Kailua house with a sprawling deck
4.92 out of 5 average rating, 13 reviews, 5 bedrooms, 7 beds, 5.5 baths
Aug 28 – Sep 2
Superhost
This beachfront Kailua estate gives you nearly an acre on the sand
5.0 out of 5 average rating, 4 reviews, 5 bedrooms, 6 beds, 3 baths
Aug 16 – 22
Superhost
This off-grid Kailua tiny house gives you a private camping experience
1 bedroom, 1 bed, No bathroom
Aug 19 – 24
Top guest favorite
Private room
This Kailua private suite puts you a 5-minute walk from the beach
4.91 out of 5 average rating, 110 reviews, 1 bedroom, 1 bed, 1 bath
Oct 13 – 18
Top guest favorite
This renovated North Shore estate puts you 30 feet from the beach, with a hot tub
5.0 out of 5 average rating, 8 reviews, 6 bedrooms, 8 beds, 4.5 baths
Aug 27 – Sep 1
Guest favorite
Private room
This Kailua garden suite puts you 1000 feet from the beach with a private patio
4.79 out of 5 average rating, 38 reviews, 2 beds, 1 bath
Aug 22 – 28
Superhost
Take in Mokulua Island views from the wrap-around lanais of this Lanikai home
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 4 baths
Aug 14 – 19
Top guest favorite
Ocean and mountain views greet you at this Makaha Valley home with a shared pool
4.92 out of 5 average rating, 48 reviews, 4 bedrooms, 5 beds, 2.5 baths
Sep 25 – 30
Top guest favorite
This Makaha Valley cottage gives you 14ft ceilings and mountain views from a tropical yard
4.97 out of 5 average rating, 117 reviews, 3 bedrooms, 4 beds, 2.5 baths
Oct 23 – 28
Top guest favorite
Hear the waves from every room of this beachfront East Shore Oahu home
5.0 out of 5 average rating, 200 reviews, 4 bedrooms, 5 beds, 2.5 baths
Sep 18 – 23
Guest favorite
Wake to ocean views from the lanai at this oceanfront Oahu condo
4.92 out of 5 average rating, 12 reviews, 1 bedroom, 2 beds, 1 bath
Aug 19 – 24