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
Guesthouse in Haleiwa
4.92 out of 5 average rating, 286 reviewsTop Beachfront Guest House/2 Pax
Guesthouse in Haleiwa
4.67 out of 5 average rating, 522 reviews1 block to beach 3 Beds!
Guesthouse in Honolulu
4.92 out of 5 average rating, 143 reviewsHale Wa’a - 2 bed/2 bath - 5 minute walk to beach!
Guesthouse in Kailua
4.78 out of 5 average rating, 137 reviewsKailua Beach Cottage - 90/TVU-0287
Guesthouses with a patio
Guesthouse in Kailua
5.0 out of 5 average rating, 4 reviewsLovely Private Kailua Cottage
Guesthouse in Honolulu
4.53 out of 5 average rating, 19 reviewsLife on the Water Hawaii
Guesthouse in Honolulu
Honolulu Paradise Vacation, free parking, WiFi A/C
Guesthouse in Laie
Close 2 Beach Entire Guest Suite
Guesthouse in Kailua
4.89 out of 5 average rating, 18 reviewsKailua's Premier Private Luxury Lofty Bungalow
Guesthouse in Kailua
5.0 out of 5 average rating, 8 reviewsThe Banyan Beach Bungalow
Guest house rentals with a washing machine and dryer
Guesthouse in Waianae
5.0 out of 5 average rating, 17 reviewsBeautiful Mountain Studio Retreat
Guesthouse in Kahuku
4.86 out of 5 average rating, 7 reviewsSpacious King bed studio
Guesthouse in Hauula
5.0 out of 5 average rating, 18 reviewsModern 1 Bed by the Beach w/Stay Discounts
Guesthouse in Kapolei
4.94 out of 5 average rating, 94 reviewsAloha Living Near Ko’olina + WiFi/Sleeps 5
Guesthouse in Haleiwa
4.86 out of 5 average rating, 110 reviewsGarden Studio, walk to Sunset Beach, 30 day rental
Guesthouse in Haleiwa
4.88 out of 5 average rating, 33 reviewsTropical Acreage + Fruit Trees + Beach ~5m drive!
Guesthouse in Pupukea
4.96 out of 5 average rating, 49 reviewsBrand New Studio with Sunset View
Guesthouse in Honolulu
4.61 out of 5 average rating, 62 reviewsManoa Valley B - Lush with Diamond Head Views
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
$146 NZD before taxes and fees
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