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 Hauula
4.87 out of 5 average rating, 87 reviewsOhana Country Cottage
3 – 10 July
Guesthouse in Waimanalo
4.83 out of 5 average rating, 36 reviewsAll Inclusive that has it all, Sleeps 8, Hot Tub
13 – 20 Apr
Guesthouse in Haleiwa
4.67 out of 5 average rating, 517 reviews1 block to beach 3 Beds!
25 Nov – 2 Dec
Guesthouse in Honolulu
4.93 out of 5 average rating, 137 reviewsHale Wa’a - 2 bed/2 bath - 5 minute walk to beach!
26 Mar – 2 Apr
Guesthouse in Kailua
4.78 out of 5 average rating, 135 reviewsKailua Beach Cottage - 90/TVU-0287
26 Apr – 3 May
Guesthouse in Haleiwa
4.83 out of 5 average rating, 59 reviewsApril & May special ! Hula House Sunset Pt. bikes
30 May – 6 June
Guesthouses with a patio
Guesthouse in Hauula
Mai Tide: New N. Shore Oceanfront, 30 Day, AC
16 – 23 Jan
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
24 – 31 Oct
Guesthouse in Laie
New place to stayClose 2 Beach Entire Guest Suite
14 – 21 Jan
Guesthouse in Honolulu
Honolulu Paradise Vacation, free parking, WiFi A/C
18 – 25 Sept
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
16 – 23 Apr
Guesthouse in Kailua
5.0 out of 5 average rating, 7 reviewsThe Banyan Beach Bungalow
2 – 9 Apr
Guest house rentals with a washing machine and dryer
Guesthouse in Waianae
5.0 out of 5 average rating, 15 reviewsBeautiful Mountain Studio Retreat
17 – 24 Dec
Guesthouse in Kahuku
5.0 out of 5 average rating, 5 reviewsSpacious King bed studio
20 – 27 Apr
Guesthouse in Haleiwa
4.87 out of 5 average rating, 31 reviewsTropical Acreage + Fruit Trees + Beach ~5m drive!
14 – 21 Aug
Guesthouse in Honolulu
4.6 out of 5 average rating, 60 reviewsManoa Valley B - Lush with Diamond Head Views
21 – 28 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
$138 AUD before taxes and fees
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