Guest house holiday rentals in Kailua
Find and book unique guest house rentals on Airbnb
Top-rated guest house rentals in Kailua
Guests agree: these guest house rentals 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 guest house rentals in Kailua
Family-friendly guest house rentals
Guest house in Hauula
4.87 out of 5 average rating, 87 reviewsOhana Country Cottage
3–10 Jul
Guest house in Waimanalo
4.83 out of 5 average rating, 36 reviewsAll Inclusive that has it all, Sleeps 8, Hot Tub
12–19 Apr
Guest house in Haleiwa
4.67 out of 5 average rating, 517 reviews1 block to beach 3 Beds!
30 Nov – 7 Dec
Guest house in Honolulu
4.93 out of 5 average rating, 137 reviewsHale Wa’a - 2 bed/2 bath - 5 minute walk to beach!
25 Mar – 1 Apr
Guest house in Haleiwa
4.92 out of 5 average rating, 281 reviewsTop Beachfront Guest House/2 Pax
6–13 Aug
Guest house in Kailua
4.78 out of 5 average rating, 135 reviewsKailua Beach Cottage - 90/TVU-0287
26 Apr – 3 May
Guest house in Haleiwa
4.83 out of 5 average rating, 59 reviewsApril & May special ! Hula House Sunset Pt. bikes
30 May – 6 Jun
Guest house rentals with a patio
Guest house in Hauula
Mai Tide: New N. Shore Oceanfront, 30 Day, AC
16–23 Jan
Guest house in Honolulu
4.53 out of 5 average rating, 17 reviewsLife on the Water Hawaii
16–23 Apr
Guest house in Kailua
Lovely Private Kailua Cottage
2–9 Apr
Guest house in Honolulu
Honolulu Paradise Vacation, free parking, WiFi A/C
18–25 Sep
Guest house in Laie
New place to stayClose 2 Beach Entire Guest Suite
17–24 Sep
Guest house in Waianae
4.93 out of 5 average rating, 44 reviewsMakaha - Ocean View Hideaway
14–21 Nov
Guest house in Kailua
4.87 out of 5 average rating, 15 reviewsKailua's Premier Private Luxury Lofty Bungalow
21–28 Sep
Guest house in Kailua
5.0 out of 5 average rating, 7 reviewsThe Banyan Beach Bungalow
2–9 Apr
Guest house rentals with a washing machine and dryer
Guest house in Waianae
5.0 out of 5 average rating, 15 reviewsBeautiful Mountain Studio Retreat
16–23 Dec
Guest house in Kahuku
5.0 out of 5 average rating, 5 reviewsSpacious King bed studio
20–27 Apr
Guest house in Haleiwa
4.87 out of 5 average rating, 31 reviewsTropical Acreage + Fruit Trees + Beach ~5m drive!
24–31 Jan
Guest house in Honolulu
4.52 out of 5 average rating, 29 reviewsHawaii guesthouse with garden (30 days)
4–11 Sep
Guest house in Honolulu
4.6 out of 5 average rating, 60 reviewsManoa Valley B - Lush with Diamond Head Views
26 Feb – 5 Mar
Guest house in Honolulu
4.82 out of 5 average rating, 200 reviewsCozy Hawaii-Kai, KokoHead, free parking, Wi-fi A/C
15–22 Dec
Quick stats about guest house 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
€ 84 before taxes and fees
Destinations to explore
- Guest house rentals United States
- House rentals United States
- Guest house rentals Hawaii
- House rentals Hawaii
- House rentals Honolulu
- House rentals Maui
- Guest house rentals Maui
- House rentals O‘ahu
- Guest house rentals O‘ahu
- House rentals Kailua
- Beachfront rentals Kailua
- Flat rentals Kailua
- Rentals with beach access Kailua
- Cottage rentals Kailua
- Fitness-friendly rentals Kailua
- Private suite rentals Kailua
- Rentals with a hot tub Kailua
- Family-friendly rentals Kailua
- Apartment rentals Kailua
- Waterfront rentals Kailua
- Beach house rentals Kailua
- Rentals with pools Kailua
- Monthly Rentals Kailua
- Beach apartment rentals Kailua
- Rentals with a patio Kailua
- Rentals with a washing machine and dryer Kailua
- Family-friendly rentals Kailua
- Rentals with outdoor seating Kailua
- Bungalow rentals Kailua
- Pet-friendly rentals Kailua
- House rentals Honolulu County
- Guest house 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