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
4.83 out of 5 average rating, 59 reviewsApril & May special ! Hula House Sunset Pt. bikes
May 30 – Jun 6
Guesthouse in Hauula
4.87 out of 5 average rating, 87 reviewsOhana Country Cottage
Jul 3 – 10
Guesthouse in Haleiwa
4.67 out of 5 average rating, 518 reviews1 block to beach 3 Beds!
Feb 20 – 27
Guesthouse in Haleiwa
4.92 out of 5 average rating, 281 reviewsTop Beachfront Guest House/2 Pax
Aug 7 – 14
Guesthouse in Honolulu
4.92 out of 5 average rating, 139 reviewsHale Wa’a - 2 bed/2 bath - 5 minute walk to beach!
Mar 9 – 16
Guesthouse in Kailua
4.78 out of 5 average rating, 135 reviewsKailua Beach Cottage - 90/TVU-0287
Oct 24 – 31
Guest house rentals with a patio
Guesthouse in Waianae
4.93 out of 5 average rating, 56 reviewsMauna 'Olu Ohana Studio
Mar 1 – 8
Guesthouse in Hauula
Mai Tide: New N. Shore Oceanfront, 30 Day, AC
Dec 30 – Jan 6
Guesthouse in Honolulu
4.56 out of 5 average rating, 18 reviewsLife on the Water Hawaii
Sep 16 – 23
Guesthouse in Kailua
Lovely Private Kailua Cottage
Apr 18 – 25
Guesthouse in Laie
New place to stayClose 2 Beach Entire Guest Suite
Jan 8 – 15
Guesthouse in Honolulu
Honolulu Paradise Vacation, free parking, WiFi A/C
Dec 8 – 15
Guesthouse in Waianae
4.93 out of 5 average rating, 45 reviewsMakaha - Ocean View Hideaway
Sep 28 – Oct 5
Guesthouse in Kailua
4.88 out of 5 average rating, 16 reviewsKailua's Premier Private Luxury Lofty Bungalow
Jul 18 – 25
Guest house rentals with a washer and dryer
Guesthouse in Honolulu
4.6 out of 5 average rating, 5 reviewsAdorable 3 bedroom guesthouse with parking
Guesthouse in Waianae
5.0 out of 5 average rating, 16 reviewsBeautiful Mountain Studio Retreat
Apr 27 – May 4
Guesthouse in Kahuku
5.0 out of 5 average rating, 5 reviewsSpacious King bed studio
Jan 1 – 8
Guesthouse in Hauula
5.0 out of 5 average rating, 16 reviewsModern 1 Bed by the Beach w/Stay Discounts
Apr 16 – 23
Guesthouse in Ewa Beach
4.95 out of 5 average rating, 349 reviewsPlumeria Resurt at the Beach
Nov 12 – 19
Guesthouse in Haleiwa
4.88 out of 5 average rating, 32 reviewsTropical Acreage + Fruit Trees + Beach ~5m drive!
Jan 2 – 9
Guesthouse in Honolulu
4.52 out of 5 average rating, 29 reviewsHawaii guesthouse with garden (30 days)
Sep 11 – 18
Guesthouse in Honolulu
4.61 out of 5 average rating, 61 reviewsManoa Valley B - Lush with Diamond Head Views
Sep 2 – 9
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
$90 before taxes and fees
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