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 Hauula
4.87 out of 5 average rating, 87 reviewsOhana Country Cottage
Jul 3 – 10
Guesthouse in Waimanalo
4.83 out of 5 average rating, 36 reviewsAll Inclusive that has it all, Sleeps 8, Hot Tub
Apr 12 – 19
Guesthouse in Haleiwa
4.67 out of 5 average rating, 517 reviews1 block to beach 3 Beds!
Nov 30 – Dec 7
Guesthouse in Honolulu
4.93 out of 5 average rating, 137 reviewsHale Wa’a - 2 bed/2 bath - 5 minute walk to beach!
Mar 25 – Apr 1
Guesthouse in Haleiwa
4.92 out of 5 average rating, 281 reviewsTop Beachfront Guest House/2 Pax
Aug 6 – 13
Guesthouse in Kailua
4.78 out of 5 average rating, 135 reviewsKailua Beach Cottage - 90/TVU-0287
Apr 26 – May 3
Guesthouse in Haleiwa
4.83 out of 5 average rating, 59 reviewsApril & May special ! Hula House Sunset Pt. bikes
May 30 – Jun 6
Guest house rentals with a patio
Guesthouse in Hauula
Mai Tide: New N. Shore Oceanfront, 30 Day, AC
Jan 16 – 23
Guesthouse in Honolulu
4.53 out of 5 average rating, 17 reviewsLife on the Water Hawaii
Apr 16 – 23
Guesthouse in Kailua
Lovely Private Kailua Cottage
Apr 2 – 9
Guesthouse in Honolulu
Honolulu Paradise Vacation, free parking, WiFi A/C
Sep 18 – 25
Guesthouse in Laie
New place to stayClose 2 Beach Entire Guest Suite
Sep 17 – 24
Guesthouse in Waianae
4.93 out of 5 average rating, 44 reviewsMakaha - Ocean View Hideaway
Nov 14 – 21
Guesthouse in Kailua
4.87 out of 5 average rating, 15 reviewsKailua's Premier Private Luxury Lofty Bungalow
Sep 21 – 28
Guesthouse in Kailua
5.0 out of 5 average rating, 7 reviewsThe Banyan Beach Bungalow
Apr 2 – 9
Guest house rentals with a washer and dryer
Guesthouse in Waianae
5.0 out of 5 average rating, 15 reviewsBeautiful Mountain Studio Retreat
Dec 16 – 23
Guesthouse in Kahuku
5.0 out of 5 average rating, 5 reviewsSpacious King bed studio
Apr 20 – 27
Guesthouse in Haleiwa
4.87 out of 5 average rating, 31 reviewsTropical Acreage + Fruit Trees + Beach ~5m drive!
Jan 24 – 31
Guesthouse in Honolulu
4.52 out of 5 average rating, 29 reviewsHawaii guesthouse with garden (30 days)
Sep 4 – 11
Guesthouse in Honolulu
4.6 out of 5 average rating, 60 reviewsManoa Valley B - Lush with Diamond Head Views
Feb 26 – Mar 5
Guesthouse in Honolulu
4.82 out of 5 average rating, 200 reviewsCozy Hawaii-Kai, KokoHead, free parking, Wi-fi A/C
Dec 15 – 22
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$18,817 GYD before taxes and fees
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