Guesthouse vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Kailua guesthouses
Family-friendly guesthouses
Guesthouse in Haleiwa
4.67 out of 5 average rating, 518 reviews1 block to beach 3 Beds!
Nov. 28 – Dec. 5
Guesthouse in Honolulu
4.92 out of 5 average rating, 139 reviewsHale Wa’a - 2 bed/2 bath - 5 minute walk to beach!
Mar. 27 – Apr. 3
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
Guesthouse in Hauula
4.87 out of 5 average rating, 87 reviewsOhana Country Cottage
Jul. 3 – 10
Guesthouses with a patio
Guesthouse in Honolulu
4.56 out of 5 average rating, 18 reviewsLife on the Water Hawaii
Oct. 16 – 23
Guesthouse in Laie
New place to stayClose 2 Beach Entire Guest Suite
Nov. 12 – 19
Guesthouse in Kailua
Lovely Private Kailua Cottage
Apr. 8 – 15
Guesthouse in Honolulu
Honolulu Paradise Vacation, free parking, WiFi A/C
Aug. 29 – Sep. 5
Guesthouse in Waianae
4.93 out of 5 average rating, 45 reviewsMakaha - Ocean View Hideaway
Dec. 23 – 30
Guesthouse rentals with a washer and dryer
Guesthouse in Kahuku
5.0 out of 5 average rating, 5 reviewsSpacious King bed studio
Aug. 25 – Sep. 1
Guesthouse in Haleiwa
4.88 out of 5 average rating, 32 reviewsTropical Acreage + Fruit Trees + Beach ~5m drive!
Mar. 16 – 23
Guesthouse in Honolulu
4.61 out of 5 average rating, 61 reviewsManoa Valley B - Lush with Diamond Head Views
Aug. 31 – Sep. 7
Guesthouse in Honolulu
4.82 out of 5 average rating, 200 reviewsCozy Hawaii-Kai, KokoHead, free parking, Wi-fi A/C
Oct. 17 – 24
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
$123 CAD before taxes and fees
Destinations to explore
- Kihei Vacation rentals
- Haleiwa Vacation rentals
- Lahaina Vacation rentals
- Kaanapali Vacation rentals
- Kahului Vacation rentals
- Ko Olina Beach Vacation rentals
- Wailea-Makena Vacation rentals
- Moloka‘i Vacation rentals
- Maui Vacation rentals
- O‘ahu Vacation rentals
- Honolulu Vacation rentals
- Waikiki Beach Vacation rentals
- Guesthouse rentals United States
- House rentals United States
- House rentals Hawaii
- Guesthouse rentals Hawaii
- House rentals Honolulu
- House rentals Maui
- Guesthouse rentals Maui
- House rentals O‘ahu
- Guesthouse rentals O‘ahu
- Pet-friendly rentals Kailua
- Rentals with outdoor seating Kailua
- Rentals with beach access Kailua
- Cottage rentals Kailua
- Rentals with a hot tub Kailua
- Monthly Rentals Kailua
- House rentals Kailua
- Beach condo rentals Kailua
- Family-friendly rentals Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Beach house rentals Kailua
- Condo rentals Kailua
- Rentals with pools Kailua
- Kid-friendly rentals Kailua
- Bungalow rentals Kailua
- Private suite rentals Kailua
- Beachfront rentals Kailua
- Apartment rentals Kailua
- Rentals with a washer and dryer Kailua
- Rentals with a patio Kailua
- House rentals Honolulu County
- Guesthouse rentals Honolulu County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom