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Search results; Over 1,000 homes in Kailua

Guest favourite
Guest house in Kailua
Absolutely Oceanfront-60'Waterfall Pool-Legal
1 bedroom, 1 bed, 1 private bathroom
30 Aug – 4 Sept
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4.81 out of 5 average rating, 209 reviews
Guest favourite
Home in Kailua
Lanikai Paradise across the street from the beach!
4 bedrooms, 5 beds, 3 bathrooms
2–7 Sept
4.9 out of 5 average rating, 50 reviews
Top guest favourite
Place to stay in Kailua
Tropical Kailua Retreat | Walk to Beach + Gym
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 131 reviews
Top guest favourite
Guest house in Kailua
Kailua Palm Studio. Walk to Beach! PERMITTED
1 bedroom, 2 beds, 1 bathroom
16–21 Sept
4.87 out of 5 average rating, 459 reviews
Superhost
Tiny home in Kailua
Brilliance In Nature
1 bedroom, 1 bed, WC
11–16 Aug
Top guest favourite
Guest suite in Kailua
Lanikai Garden Studio - Licensed - Since 1985!
1 king bed, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Kailua
Hale Oahu Estate- Kailua BeachFront- Lic. Rental #
6 bedrooms, 7 beds, 4 bathrooms
2–7 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Kailua
Place in Paradise-Kailua Beach Front Lic. Rental:
5 bedrooms, 7 beds, 5.5 bathrooms
28 Aug – 2 Sept
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Kailua
Palione Papalani - Kailua License #1990/NUC-1787
6 bedrooms, 12 beds, 5.5 bathrooms
28 Nov – 5 Dec
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Kaaawa
Newly Renovated Beachfront Estate
6 bedrooms, 8 beds, 4.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest suite in Kailua
Licensed Lanikai Tree House - Since 1985!
1 bedroom, 1 king bed, 1 bathroom
4–11 Sept
5.0 out of 5 average rating, 29 reviews
Superhost
Home in Kailua
Kailuana Beachfront Estate
5 bedrooms, 6 beds, 3 bathrooms
16–22 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Waianae
4 beds, Near Beach, Pool, Spa, Gym, Ocean Views
4 bedrooms, 5 beds, 2.5 bathrooms
25–30 Sept
4.91 out of 5 average rating, 47 reviews
Superhost
Tiny home in Kailua
Disconnect Off Grid
1 bedroom, 1 bed, No bathroom
19–24 Aug
Top guest favourite
Guest suite in Kailua
Aloha suite
1 bedroom, 1 queen bed, 1 bathroom
13–18 Oct
4.91 out of 5 average rating, 110 reviews
Top guest favourite
Home in Hauula
Moeʻuhane Kai Beach Front Home
4 bedrooms, 5 beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 200 reviews
Guest favourite
Home in Makaha Valley
3 BDRM, Near beach, Free Prking, HotTub, Pool, Gym
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.97 out of 5 average rating, 35 reviews
Superhost
Home in Honolulu
Hale Hoomalie- Peaceful Manoa Valley Retreat near
2 bedrooms, 2 queen beds, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Kahuku
Turtle Bay Hale: Renovated 2025, Golf Course Front
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 53 reviews