Search Kailua Guest Houses

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Featured Guest Houses in Kailua

Lovely Private Kailua Cottage
9.8 out of 10, Exceptional, (20)
"Gracious host. Very welcoming. Very comfortable lodging in a central location convenient to the beach and vibrant town of Kailua. "
Lovely Private Kailua Cottage
This property is no longer available
9.8 out of 10, Exceptional, (23)
"Great location right near diamond head! There were several restaurants within walking distance. Host was responsive. We would definitely stay here again on our next visit. "
This property is no longer available
Beautiful Kailua Hale Studio
10.0 out of 10, Exceptional, (51)
"Great apartment and location. The owner provided everything necessary for a great stay: fully functional kitchen and living areas, beach chairs and umbrella, boogie boards, free washer and dryer, TV. Owner was very communicative and pleasant to work with. Will definitely stay again when in Kailua. "
Beautiful Kailua Hale Studio
Cozy Kaaawa Studio with Mountain Views - 30 Day Min
9.8 out of 10, Exceptional, (25)
"The studio looks just like the pictures. Very comfortable and clean. Nicely maintained landscaping, well equipped, outdoor shower to rinse off the beach sand. Friendly and helpful onsite host. Beautiful view of the Koolau mountains. We will definitely stay here again! Thank you Angelo and Micah. 🏝️"
Cozy Kaaawa Studio with Mountain Views - 30 Day Min
Home of Aloha, 5 Bedrooms / 4 Baths, Sleeps 14
9.6 out of 10, Exceptional, (4)
"The home was beautiful. Very comfortable. Biggest drawback was the proximity to a very busy highway. Lots of highway noise, including many sirens day and night."
Home of Aloha, 5 Bedrooms / 4 Baths, Sleeps 14
Kaaawa Home With Mountain View’s - 30 Day Min
9.8 out of 10, Exceptional, (32)
"I wanted to thank you for the opportunity to stay in your place. I love this home, location and time that we spend there It is amazing place, amazing hosts. You can not wish for anything more."
Kaaawa Home With Mountain View’s - 30 Day Min
Walking Distance for 2Br X 2Bath Near Waikiki Beach Resort Area.
9.8 out of 10, Exceptional, (10)
"This was a great place to stay. Easy parking and location was good for us. Away from hustle and crowds of downtown! But easy to get around."
Walking Distance for 2Br X 2Bath Near Waikiki Beach Resort Area.
Island Paradise home 5 min from the beach
Island Paradise home 5 min from the beach
A lovely ohana with ocean view
10.0 out of 10, Exceptional, (1)
"we had a great time and the hosts were great. could not have asked for such a perfect vacation!"
A lovely ohana with ocean view
DaLight - A beautiful home in a quiet neighborhood
9.0 out of 10, Wonderful, (2)
"The house is one of the nicest I have stayed in in Kailua. The room was a little warm at night when I was trying to sleep but Adrien (the home owner) told me they have a plan to fix that."
DaLight - A beautiful home in a quiet neighborhood
This property is no longer available.
This property is no longer available.
Honolulu for Spring Break 2023
Honolulu for Spring Break 2023
Room in Holiday House - Hgvc Hawaiian Village Resort & Spa, Hot Tub, Pool!
2.0 star property
Room in Holiday House - Hgvc Hawaiian Village Resort & Spa, Hot Tub, Pool!
Newly renovated guest house with lush landscaping & gazebo
2.0 star property
Newly renovated guest house with lush landscaping & gazebo
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Kailua

Private Beachfront Rental
9.8 out of 10, Exceptional, (210)
"Shari was a warm and responsive host and her accommodation was right on the beach!"
Private Beachfront Rental
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
9.0 out of 10, Wonderful, (123)
"Wonderful location. Steps to the beach to watch the morning sunrise. "
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
Aston Waikiki Sunset
4.0 star property
7.8 out of 10, Good, (2826)
"Everything from checkin to checkout was amazing 👌"
The price is AU$387
includes taxes & fees
22 Nov - 23 Nov
Aston Waikiki Sunset
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.