View All Kailua HI Homes with Guest House Listings
Welcome home to this sweet house on a quiet cul-de-sac in Keolu Hills. This charming 4 bedroom 3 bathroom with an open concept floor plan makes for easy island living. N...
- 4 Beds
- 3 Baths
- 202613493 MLS
- FS - Fee Simple Tenure
- 12 DOM
Nestled in the highly desirable Keolu Hills neighborhood, this fully renovated Kailua home offers the perfect blend of comfort, convenience, and island living. Situated o...
- 4 Beds
- 3 Baths
- 202608198 MLS
- FS - Fee Simple Tenure
- 91 DOM
Rarely available: large lot with 2 homes on one of Lanikai’s most coveted beach streets. It's easy to fall in love with this dream property where privacy, luxury, and lif...
- 6 Beds
- 5 Baths
- 202600468 MLS
- FS - Fee Simple Tenure
- 112 DOM
The Mokulua Estate is a breathtaking oceanfront sanctuary set within the prestigious Lanikai neighborhood. This exceptional property offers unobstructed views of the Moku...
- 9 Beds
- 10 Baths
- 202600075 MLS
- FS - Fee Simple Tenure
- 194 DOM
The Windsurfer at Kalilua Beach Park is one of the more exclusive locations in Kailua, as it is across the street from the Kailua Beach Park. This location affords you wa...
- 2 Beds
- 3 Baths
- 202524947 MLS
- FS - Fee Simple Tenure
- Windsurfer Bldg.
- 36 DOM
NEW IMPROVED LIST PRICE! Welcome to House Beautiful in the sought after Kaimalino neighborhood. Located in a great spot just a few doors down from the access point to Tu...
- 4 Beds
- 3 Baths
- 202526138 MLS
- FS - Fee Simple Tenure
- 101 DOM
Enjoy the very best of Kailua living in this charming single-level home (built in 2012) in Coconut Grove, perfectly located near Kailua Beach, shops, and cafes. The main ...
- 2 Beds
- 2 Baths
- 202526097 MLS
- FS - Fee Simple Tenure
- 38 DOM
Open House Sunday, Oct 5, 12–3 PM. Imagine waking up every morning to breathtaking Ko'olau Mountain views in your own Maunawili Estates retreat. This beautifully maintain...
- 4 Beds
- 3 Baths
- 202518270 MLS
- FS - Fee Simple Tenure
- 43 DOM
Half a mile to the beach and 3/4 mile to Kailua Town! Enjoy all Kailua has to offer just moments from this gem of a house. The main living area features 3 bedrooms, 1.5 b...
- 3 Beds
- 2 Baths
- 202511464 MLS
- FS - Fee Simple Tenure
- 86 DOM
Welcome to this single-level home with two attached studio units on a spacious 10,000+ sq ft corner lot in desirable Kalaheo Hillside, Kailua. Just a half mile from the ...
- 3 Beds
- 4 Baths
- 202509923 MLS
- FS - Fee Simple Tenure
- 37 DOM
Welcome to 17 Laiki, now publicly available for the first time. Completed in 2022, it is one of the newest beachfront homes on Kailua Beach. Expansive and private, the ho...
- 7 Beds
- 7 Baths
- 202507302 MLS
- FS - Fee Simple Tenure
- 184 DOM
Rare opportunity to own a 2-acre estate in Norfolk, Kailua—renowned for its privacy, breathtaking views, and country feel with urban convenience. This unique property fea...
- 5 Beds
- 3 Baths
- 202506716 MLS
- FS - Fee Simple Tenure
- 96 DOM
From the peaceful sound of waterfalls to an oasis of koi ponds and lagoons, colorful natural landscaping, and unbelievably striking mountain views, Windward Harbour is a ...
- 3 Beds
- 2 Baths
- 202505003 MLS
- FS - Fee Simple Tenure
- Windward Harbour Bldg.
- 63 DOM
PRICE REDUCTION!! Flexible Home - The main house features 2 bedrooms plus a versatile den that functions beautifully as a 3rd bedroom, along with a full bath. For added f...
- 4 Beds
- 2 Baths
- 202502016 MLS
- FS - Fee Simple Tenure
- 86 DOM
A GREAT HOUSE" Top of the 8th Tee Box at Mid Pac Country Clubs GOLF COURSE with a SWIMMING POOL & Guest Cottage ... it's the trifecta. On the back side of Mid Pac Count...
- 5 Beds
- 4 Baths
- 202404898 MLS
- FS - Fee Simple Tenure
- 55 DOM
A picturesque property idyllically located steps away from Kailua Bay, one of the most beautiful stretches of beach in the world. This expansive estate has 7 bedrooms/6 b...
- 7 Beds
- 6 Baths
- 202319681 MLS
- FS - Fee Simple Tenure
- 61 DOM
Enjoy this beautiful 4 bedroom, 3 bath beach home with breathtaking views located just steps away from Kailua Beach Park. This home offers you a wonderful Kailua lifestyl...
- 4 Beds
- 3 Baths
- 202303341 MLS
- FS - Fee Simple Tenure
- 169 DOM
Welcome Home! This stunning corner unit offers 3 bedrooms, 2 bathrooms, and 1,307 square feet of stylish island living. This turn-key home is ready for you to move in and...
- 3 Beds
- 2 Baths
- 202421701 MLS
- FS - Fee Simple Tenure
- Aikahi Gardens Bldg.
- 45 DOM
HUGE VALUE!!! Welcome Home to this highly sought after Aikahi Gardens 3 bedroom townhouse with 2.5 baths! The kitchen, bathrooms, floors, windows and floors were renovate...
- 3 Beds
- 3 Baths
- 202424439 MLS
- FS - Fee Simple Tenure
- Aikahi Gardens Bldg.
- 66 DOM
Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Kailua, HI · Curated MLS Search
Homes with Guest House in Kailua, HI
An editorially curated view of every active homes with guest house listing in Kailua, HI. Updated in real time from the local MLS, presented without the noise.
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