Guesthouse vacation rentals in Kailua
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Kailua
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Kailua guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Haleiwa
4.92 out of 5 average rating, 287 reviewsTop Beachfront Guest House/2 Pax
Guesthouse in Haleiwa
4.67 out of 5 average rating, 524 reviews1 block to beach 3 Beds!
Guesthouse in Kahala-Waialae
4.92 out of 5 average rating, 145 reviewsHale Wa’a - 2 bed/2 bath - 5 minute walk to beach!
Guesthouse in Kailua
4.78 out of 5 average rating, 138 reviewsKailua Beach Cottage - 90/TVU-0287
Guesthouse in Hauula
4.87 out of 5 average rating, 87 reviewsOhana Country Cottage
Guest house rentals with a patio
Guesthouse in Hawaii Kai
4.5 out of 5 average rating, 20 reviewsLife on the Water Hawaii
Guesthouse in Kailua
5 out of 5 average rating, 7 reviewsLovely Private Kailua Cottage
Guesthouse in Hawaii Kai
Honolulu Paradise Vacation, free parking, WiFi A/C
Guesthouse in Kailua
4.89 out of 5 average rating, 18 reviewsKailua's Premier Private Luxury Lofty Bungalow
Guesthouse in Kailua
5 out of 5 average rating, 9 reviewsThe Banyan Beach Bungalow
Guest house rentals with a washer and dryer
Guesthouse in Haleiwa
4.89 out of 5 average rating, 36 reviewsTropical Acreage + Fruit Trees + Beach ~5m drive!
Guesthouse in Hauula
5 out of 5 average rating, 6 reviewsShoreside Cottage
Guesthouse in Kaneohe
Ko'olau - Tranquil escape with stunning views
Guesthouse in Upper Manoa
4.62 out of 5 average rating, 63 reviewsManoa Valley B - Lush with Diamond Head Views
Guesthouse in Hawaii Kai
4.82 out of 5 average rating, 200 reviewsCozy Hawaii-Kai, KokoHead, free parking, Wi-fi A/C
Quick stats about guesthouse rentals in Kailua
Total rentals
30 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
2.1K reviews
Nightly prices starting at
G$18,867 GYD before taxes and fees
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