Search Guest Houses in Kailua

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Kailua Guest Houses

Steps to the Beach Guesthouse

9.8 out of 10, Exceptional, (85)
"Great location, close to wonderful Kailua beach. Beautiful house very quiet and safe neighborhood "
Steps to the Beach Guesthouse

Private space in paradise

9.6 out of 10, Exceptional, (99)
"Great spot, clean, quiet, friendly, relaxing, helpful, picturesque."
Private space in paradise

Kaaawa Home With Mountain View’s - 30 Day Min

9.8 out of 10, Exceptional, (33)
"This place is great, the house was perfect and neighbohood is chill. Thank you Angelo, we had a great time."
Kaaawa Home With Mountain View’s - 30 Day Min

A Hidden Jewel, ideal for a family or Corporate Retreat

9.0 out of 10, Wonderful, (108)
"Great place to stay! Host is very helpful and is always ready to assist when issues or questions arise. We had a blast! "
A Hidden Jewel, ideal for a family or Corporate Retreat

Newly renovated guest house with lush landscaping & gazebo

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a work trip so it worked out really nice and centrally located. "
Newly renovated guest house with lush landscaping & gazebo

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

Lovely Private Kailua Cottage

10.0 out of 10, Exceptional, (21)
"We enjoyed our stay immensely."
Lovely Private Kailua Cottage

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

Beautiful Kailua Hale Studio

10.0 out of 10, Exceptional, (56)
"This property provided everything we needed. The location was great as it was just a short walk or bike ride to either the beach or town. The bikes were provided by the owners as well as beach chairs, coolers etc. The owners were awesome and communicated check in, amenities, nearby restaurants, beaches, stores and everything we needed clearly and made for an easy, enjoyable stay. We will be back and we highly recommend."
Beautiful Kailua Hale Studio

Hawaiian plantation-style home, perfect for families.

10.0 out of 10, Exceptional, (16)
"Close to beach and mountains, a country vacation, yet close to any needs. Loved it"
Hawaiian plantation-style home, perfect for families.

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

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!
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

What are the most popular guest houses in Kailua according to reviews?
Beautiful Kailua Hale Studio is an outstanding choice for travellers seeking an exceptional stay in Kailua, boasting a superb 10.0 rating. Guests rave about the fantastic location and the warm hospitality of the host, making it an ideal spot for couples or solo adventurers eager to soak in the serene surroundings. The historic charm of the property adds a unique touch, inviting guests to unwind in comfort.

For families or groups, the Quiet, Private, Beachy 2-bedroom guesthouse is a stellar option, also rated 10.0. This spacious haven is just a short walk from Kailua Beach, allowing for easy beach days filled with sun and sand. Equipped with a full kitchen, including modern appliances like a dishwasher and oven, family mealtimes become a breeze. The cozy deck is superb for evening gatherings, giving everyone a chance to relax and enjoy the beautiful Hawaiian evenings.

Steps to the Beach Guesthouse, with an impressive 9.8 rating, is another gem that caters to both couples and families. This property is designed to provide convenience with its well-appointed kitchen, making meal preparation simple after a day of exploring. The inviting deck and patio areas are superb for enjoying breakfast in the morning sun or unwinding under the stars in the evening.
What is the nightly rate for a guest house in Kailua?
Rates for Kailua guest houses vary, but travelers can find great-value prices with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Kailua guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
Are there any family-friendly guest houses in Kailua?
The Beautiful Kailua Hale Studio is a fantastic choice for families visiting Kailua. This cozy and well-equipped guesthouse features essential amenities like a TravelCrib and dinnerware designed specifically for children, making it easy for parents to settle in with their little ones. With a fully stocked kitchen and a collection of books to enjoy, families can create a home-away-from-home atmosphere while relishing quality time together.

Another excellent option is the Quiet, Private, Beachy 2-bedroom guesthouse, just a short stroll from Kailua Beach. This property is great for families, offering not only a TravelCrib but also toys for children and a stair gate to ensure safety for younger kids. The spacious layout includes a fully functional kitchen, a patio for outdoor relaxation, and modern conveniences like a dishwasher and microwave, which add to the convenience of family meals after a day of adventures.

For those who prioritize proximity to the beach, the Steps to the Beach Guesthouse is an ideal pick. It boasts a inviting space and practical amenities such as a kitchen and patio, allowing families to enjoy meals al fresco. With easy access to the beautiful Kailua Beach, this guesthouse provides the great launching point for family-friendly activities like swimming, building sandcastles, and enjoying sunset picnics.
What's the difference between a Kailua guest house and a B&B?
A guest house in Kailua is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.