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.

Superhost
Guesthouse in Haleiwa
Walk to Beach Large Studio
1 Block to Beach, Spacious Studio. *Inquire available dates!!* Comfortable, Safe neighborhood. Has queen bed, Hotel style kitchen with toaster/convection oven, microwave, coffee maker, mini fridge/freezer and Outdoor shower. The toilet is inside unit behind carved bali privacy screen. Private Entrance, & FREE off street parking, which is quite a Privilege! (street parking is also an option, if available). It is a very comfortable, clean, affordable place to stay in Most Desirable Location.
Dec 6 – 13
$169 per night
4.78 out of 5 average rating, 246 reviews
Guest favorite
Guesthouse in Haleiwa
Top Beachfront Guest House/2 Pax
This 1BR beachfront guest house, is right at Banzai beach! This North Shore destination is ideal for an exclusive romantic retreat. Newly built and elegantly designed, this rental has a relaxed, minimalist aesthetic. Take in the sea breeze and beautiful sunsets from the private balcony. Walk to the sandy shore in just a few steps. Not suitable for children. Not suitable for guest with visitors due to limited parking space & trash disposal system. 1 parking space per booking. NO pets allowed.
Jun 27 – Jul 4
$500 per night
4.92 out of 5 average rating, 272 reviews
Guest favorite
Guesthouse in Kailua
Kailua's Premier Private Luxury Beach Bungalow
Kailua's Original Beach Bungalow premier private luxury bungalow getaway ~ Modern design mingles with traditional elegance in this newly renovated bungalow. Beautifully furnished with comfort and ease-open floor plan that features large floor to ceiling windows. Very private - with a large gated spacious patio - hot and cold running outdoor shower, outdoor private dining and just steps from your bungalow down the path to the most beautiful beach in the world.
May 24 – 31
$499 per night
4.86 out of 5 average rating, 139 reviews

Popular amenities for Kailua guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Honolulu
Hale Wa’a - 2 bed/2 bath - 5 minute walk to beach!
Dec 8 – 15
$433 per night
4.93 out of 5 average rating, 131 reviews
Superhost
Guesthouse in Hauula
Ohana Country Cottage
Jul 3 – 10
$395 per night
4.87 out of 5 average rating, 87 reviews
Guest favorite
Guesthouse in Haleiwa
Beach Cottage w bikes/ 1 stay per month
Jun 21 – 28
$250 per night
4.89 out of 5 average rating, 89 reviews
Guesthouse in Kailua
Kailua Beach Cottage - 90/TVU-0287
Nov 4 – 11
$450 per night
4.77 out of 5 average rating, 132 reviews
Guest favorite
Guesthouse in Honolulu
Peace House
$159 per night
4.73 out of 5 average rating, 139 reviews
Superhost
Guesthouse in Haleiwa
1 block to beach 3 Beds!
Nov 25 – Dec 2
$269 per night
4.67 out of 5 average rating, 514 reviews
Superhost
Guesthouse in Haleiwa
Hula House Sunset Pt w bikes/1 stay per month
Nov 12 – 19
$165 per night
4.83 out of 5 average rating, 59 reviews

Guest house rentals with a patio

Guest favorite
Guesthouse in Kailua
Kailua Surf Shack: Your Hawaiian Adventure!
Aug 18 – 25
$294 per night
4.95 out of 5 average rating, 56 reviews
Guest favorite
Guesthouse in Haleiwa
Beachfront *Studio*, North Shore Oahu
May 11 – 18
$399 per night
4.87 out of 5 average rating, 45 reviews
Guest favorite
Guesthouse in North Shore
Serene Mountain Getaway with Ocean Views
Oct 4 – 11
$198 per night
5.0 out of 5 average rating, 63 reviews
Guest favorite
Guesthouse in Waianae
Mauna ‘Olu Ohana House
Mar 27 – Apr 3
$175 per night
4.91 out of 5 average rating, 47 reviews
Superhost
Guesthouse in Honolulu
Honolulu Paradise Vacation, free parking, WiFi A/C
Nov 22 – 29
$195 per night
New place to stay
Guesthouse in Kailua
Kailua cottage
Dec 12 – 19
$198 per night
4.71 out of 5 average rating, 21 reviews
Guesthouse in Kailua
Lovely Private Kailua Cottage
Nov 18 – 25
$353 per night
New place to stay
Guesthouse in Honolulu
Life on the Water Hawaii
Nov 8 – 15
$191 per night
4.42 out of 5 average rating, 12 reviews
Guest favorite
Guesthouse in Waianae
Makaha - Ocean View Hideaway
Aug 12 – 19
$180 per night
4.94 out of 5 average rating, 34 reviews
Superhost
Guesthouse in Kailua
Kailua's Premier Private Luxury Lofty Bungalow
Jun 20 – 27
$426 per night
4.83 out of 5 average rating, 12 reviews
Superhost
Guesthouse in Kailua
The Banyan Beach Bungalow
Aug 26 – Sep 2
$499 per night
5.0 out of 5 average rating, 3 reviews

Guest house rentals with a washer and dryer

Superhost
Guesthouse in Hauula
Brand New, Beach Front, Villa Aloha 30-day min
Nov 21 – 28
$648 per night
4.88 out of 5 average rating, 129 reviews
Guest favorite
Guesthouse in Kailua
Lanikai Oasis, 2 beds, 5 min walk to the beach!
Sep 5 – 12
$495 per night
4.92 out of 5 average rating, 36 reviews
Guest favorite
Guesthouse in Hauula
Dreamy, Beach style w/ gorgeous North Shore beach!
Sep 25 – Oct 2
$383 per night
4.89 out of 5 average rating, 72 reviews
Superhost
Guesthouse in Waimanalo
Palm Tree Studio - Beach, A/C, Clean
Mar 30 – Apr 6
$200 per night
4.75 out of 5 average rating, 4 reviews
Superhost
Guesthouse in Honolulu
Manoa Valley Duplex with Mountain and Ocean Views
Jan 5 – 12
$413 per night
4.9 out of 5 average rating, 67 reviews
Superhost
Guesthouse in Kahuku
Newly Built Beachfront Tiny House on North Shore
Feb 25 – Mar 4
$483 per night
4.75 out of 5 average rating, 4 reviews
Superhost
Guesthouse in Honolulu
Hawaii guesthouse with garden (30 days)
Mar 5 – 12
$247 per night
4.52 out of 5 average rating, 29 reviews
Guest favorite
Guesthouse in Waianae
Beautiful Mountain Studio Retreat
Oct 21 – 28
$225 per night
5.0 out of 5 average rating, 14 reviews
Superhost
Guesthouse in Kahuku
Spacious King bed studio
Aug 22 – 29
$196 per night
5.0 out of 5 average rating, 4 reviews
Guesthouse in Kailua
Lanikai Kailua 1-bedroom apartment
May 31 – Jun 7
$100 per night
4.7 out of 5 average rating, 10 reviews
Guesthouse in Hauula
Modern 1 Bed by the Beach w/Stay Discounts
Aug 22 – 29
$193 per night
5.0 out of 5 average rating, 10 reviews
Guesthouse in Haleiwa
Sunset Beach Studio - Budget/Eco Friendly
May 21 – 28
$135 per night
4.64 out of 5 average rating, 78 reviews

Quick stats about guesthouse rentals in Kailua

Total rentals

40 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

40 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

1.9K reviews

Nightly prices starting at

$90 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Hawaii
  4. Honolulu County
  5. Kailua
  6. Guesthouse rentals