Guesthouse holiday rentals in Kailua
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in Kailua
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Kailua guesthouses
Family-Friendly guesthouses
Guesthouse in Haleiwa
4.92 out of 5 average rating, 281 reviewsTop Beachfront Guest House/2 Pax
6–13 Aug
Guesthouse in Waimanalo
4.83 out of 5 average rating, 36 reviewsAll Inclusive that has it all, Sleeps 8, Hot Tub
17–24 Nov
Guesthouse in Haleiwa
4.67 out of 5 average rating, 517 reviews1 block to beach 3 Beds!
10–17 Jan
Guesthouse in Honolulu
4.93 out of 5 average rating, 137 reviewsHale Wa’a - 2 bed/2 bath - 5 minute walk to beach!
19–26 Mar
Guesthouse in Kailua
4.78 out of 5 average rating, 135 reviewsKailua Beach Cottage - 90/TVU-0287
21–28 Feb
Guesthouse in Hauula
4.87 out of 5 average rating, 87 reviewsOhana Country Cottage
3–10 Jul
Guesthouses with a patio
Guesthouse in Honolulu
4.53 out of 5 average rating, 17 reviewsLife on the Water Hawaii
16–23 Apr
Guesthouse in Kailua
Lovely Private Kailua Cottage
15–22 Mar
Guesthouse in Honolulu
Honolulu Paradise Vacation, free parking, WiFi A/C
19–26 Feb
Guesthouse in Waianae
4.93 out of 5 average rating, 44 reviewsMakaha - Ocean View Hideaway
14–21 Nov
Guesthouse in Kailua
4.87 out of 5 average rating, 15 reviewsKailua's Premier Private Luxury Lofty Bungalow
26 Sep – 3 Oct
Guesthouse in Kailua
5.0 out of 5 average rating, 6 reviewsThe Banyan Beach Bungalow
29 Jun – 6 Jul
Guest house rentals with a washing machine and dryer
Guesthouse in Kapolei
4.93 out of 5 average rating, 91 reviewsAloha Living Near Ko’olina + WiFi/Sleeps 5
31 Aug – 7 Sep
Guesthouse in Haleiwa
4.87 out of 5 average rating, 31 reviewsTropical Acreage + Fruit Trees + Beach ~5m drive!
19–26 Feb
Guesthouse in Honolulu
4.6 out of 5 average rating, 60 reviewsManoa Valley B - Lush with Diamond Head Views
26 Feb – 5 Mar
Guesthouse in Honolulu
4.82 out of 5 average rating, 200 reviewsCozy Hawaii-Kai, KokoHead, free parking, Wi-fi A/C
15–22 Dec
Quick stats about guesthouse rentals in Kailua
Total rentals
30 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
30 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
2.1K reviews
Nightly prices starting at
$152 NZD before taxes and fees
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