View All Kailua HI Homes with Guest Room Listings
Completed in 2022, this classic beachfront home was redesigned into a spacious, modern property. 21 Kalaka's unique elevation offers commanding views and privacy; feature...
- 5 Beds
- 5 Baths
- 202613970 MLS
- FS - Fee Simple Tenure
- 7 DOM
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
Oceanfront elegance awaits in this exceptional Kaimalino residence, perfectly positioned to capture panoramic views of Kailua Bay, the Mokulua Islands, and the majestic K...
- 4 Beds
- 4 Baths
- 202612440 MLS
- FS - Fee Simple Tenure
- 28 DOM
Tucked onto one of Kalaheo Hillside's most sought-after streets, 445 Iliwahi Loop is a fully reimagined 4-bed, 3-bath retreat blending timeless island architecture with a...
- 4 Beds
- 3 Baths
- 202611972 MLS
- FS - Fee Simple Tenure
- 34 DOM
Welcome to Gardenia Manor! This beautifully maintained 2-bedroom, 1-bath corner end-unit offers the perfect combination of comfort, convenience and indoor-outdoor living....
- 2 Beds
- 1 Baths
- 202610676 MLS
- FS - Fee Simple Tenure
- Gardenia Manor Bldg.
- 34 DOM
Aikahi Gardens spacious 2 bedroom 1.5 bath unit with 2 parking stalls in front of unit, plenty of guest parking and a large beautifully titled courtyard area. Recent upg...
- 2 Beds
- 2 Baths
- 202611566 MLS
- FS - Fee Simple Tenure
- Aikahi Gardens Bldg.
- 41 DOM
This is where your Kailua story begins. Nestled on a quiet street in the heart of sought-after Enchanted Lake, this inviting home blends comfort, style, and island charm....
- 3 Beds
- 2 Baths
- 202601803 MLS
- FS - Fee Simple Tenure
- 41 DOM
This estate offers a rare blend of scale & versatility in one of Oahu’s most coveted enclaves. Lanikai Living- with incredible ocean views, a private pool & spa, flat bac...
- 7 Beds
- 5 Baths
- 202606176 MLS
- FS - Fee Simple Tenure
- 28 DOM
Experience tranquil beachfront living in one of the most pristine areas along Kailua Beach, featuring stunning ocean views from the modern kitchen, spacious living room, ...
- 4 Beds
- 5 Baths
- 202609316 MLS
- FS - Fee Simple Tenure
- 77 DOM
Welcome home! Charming Poinciana Manor two bedroom, two bath condo. This corner unit has easy access to the two covered parking stalls, elevator, and stairs. The spacious...
- 2 Beds
- 2 Baths
- 202606620 MLS
- FS - Fee Simple Tenure
- Poinciana Manor Bldg.
- 40 DOM
Tucked back in the peaceful Keolu Hills neighborhood sits this charming single-story home. Located on a dead-end street, you’ll appreciate the minimal street noise and tr...
- 3 Beds
- 2 Baths
- 202607246 MLS
- FS - Fee Simple Tenure
- 97 DOM
Welcome to Windward Cove, a gated tropical oasis in the heart of Kailua. This beautifully refreshed ground-floor 3-bedroom, 2-bath residence offers the best of beach-town...
- 3 Beds
- 2 Baths
- 202607605 MLS
- FS - Fee Simple Tenure
- Windward Cove Bldg.
- 37 DOM
Exquisite beachfront estate on coveted Dune Circle in Kailua, tucked away on a quiet cul-de-sac. Built in 2006, this sophisticated custom residence seamlessly blends luxu...
- 3 Beds
- 4 Baths
- 202606968 MLS
- FS - Fee Simple Tenure
- 105 DOM
$39k PRICE DROP… COME & GET IT!!! Beautifully renovated in 2022 and tucked into one of Kailua’s most beloved neighborhoods, this single-story home offers the relaxed isla...
- 3 Beds
- 2 Baths
- 202602237 MLS
- FS - Fee Simple Tenure
- 81 DOM
Welcome to your beachside paradise—just one lot from the ocean and directly next to the beach pathway on a quiet cul-de-sac. This lovingly maintained and upgraded 4-bedro...
- 4 Beds
- 2 Baths
- 202600924 MLS
- FS - Fee Simple Tenure
- 138 DOM
Welcome home to this luxurious tri-level 3-bedroom, 2.5-bath corner townhouse in Bluestone, Kailua’s premier gated community. Bordered by preservation land and the Mid Pa...
- 3 Beds
- 3 Baths
- 202601527 MLS
- FS - Fee Simple Tenure
- Bluestone Bldg.
- 31 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
Welcome to Bluestone: Live the ultimate Kailua lifestyle! Discover this exquisite, light-filled 3-bed, 3-bath retreat in one of O'ahu's most desired gated communities....
- 3 Beds
- 3 Baths
- 202527612 MLS
- FS - Fee Simple Tenure
- Bluestone Bldg.
- 69 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
Welcome to your dream home in the highly sought-after Kailua Bluffs neighborhood! This beautifully updated 4-bedroom, 2.5-bath residence offers the perfect blend of comfo...
- 4 Beds
- 3 Baths
- 202523859 MLS
- FS - Fee Simple Tenure
- 31 DOM
PRICE DROP TO $899,000 + BUYER CREDIT OF 40K Experience sophisticated island living in this stunning Windward Passage condo, in the heart of Kailua, just blocks to sho...
- 3 Beds
- 2 Baths
- 202524065 MLS
- FS - Fee Simple Tenure
- Windward Passage Bldg.
- 234 DOM
SELLER MOTIVATED & PRICE REDUCED. Lowest-Priced Residence in Bluestone. Rarely available, generously sized 2-bedroom, 2.5-bath residence offering over 1,500sqft of interi...
- 2 Beds
- 3 Baths
- 202523276 MLS
- FS - Fee Simple Tenure
- Bluestone Bldg.
- 204 DOM
Experience island living with this turn-key 6-bedroom, 4-bath Kailua retreat! Located on a private cul-de-sac, this home offers a resort-style lifestyle with a pool, wat...
- 6 Beds
- 4 Baths
- 202522102 MLS
- FS - Fee Simple Tenure
- 119 DOM
This impeccable Lanikai residence is an architectural gem, crafted with exquisite millwork & detail. Built in 2014, it offers the timeless charm of Hawaii's plantation st...
- 5 Beds
- 4 Baths
- 202517517 MLS
- FS - Fee Simple Tenure
- 41 DOM
Experience Iconic Beachside Living at 28 Pu‘ukani Place, Kailua. Nestled on a private road in one of Hawaii’s most coveted coastal communities, this mid-century modern tw...
- 3 Beds
- 3 Baths
- 202516766 MLS
- FS - Fee Simple Tenure
- 31 DOM
Welcome to this exceptional Kailua beachfront estate. This gated resort-like retreat is situated on nearly an acre of land fronting one of the most beautiful beaches in ...
- 12 Beds
- 16 Baths
- 202520168 MLS
- FS - Fee Simple Tenure
- 318 DOM
Rare 2.75% VA Assumable Opportunity in Kailua! Fall in love w/ this beautifully renovated home featuring a flexible floor plan perfect for multi-generational living or re...
- 5 Beds
- 2 Baths
- 202518717 MLS
- FS - Fee Simple Tenure
- 133 DOM
Completed in 2022, this custom home blends high-end finishes with thoughtful design in a prime Kailua location. The main living area features vaulted ceilings and opens t...
- 4 Beds
- 6 Baths
- 202517832 MLS
- FS - Fee Simple Tenure
- 85 DOM
Ka Malanai at Kailua is a prime location in the heart of vibrant Kailua Town! This 2-bdm, 2-bath residence offers the perfect blend of contemporary style, comfort, and co...
- 2 Beds
- 2 Baths
- 202512372 MLS
- FS - Fee Simple Tenure
- Ka Malanai At Kailua Bldg.
- 40 DOM
Welcome to this beautiful 2 bedroom, 2 bath condo at Poinciana Manor in the heart of Kailua town. This move-in ready unit has been completely remodeled over the years and...
- 2 Beds
- 2 Baths
- 202513972 MLS
- FS - Fee Simple Tenure
- Poinciana Manor Bldg.
- 34 DOM
This newly renovated Bluestone end-unit is located on the Lanikai side, in one of the most private locations in the complex, with open space on one side and preservation ...
- 3 Beds
- 3 Baths
- 202513201 MLS
- FS - Fee Simple Tenure
- Bluestone Bldg.
- 70 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
Experience the Best of Kailua Living! This nicely updated split-level 2-bedroom, 1.5-bath residence is located in the heart of highly desirable Kailua Town—a vibrant and ...
- 2 Beds
- 2 Baths
- 202510062 MLS
- FS - Fee Simple Tenure
- Koolau Vista Bldg.
- 39 DOM
All plumbing work had been completed on this incredible unit!!!!!! Welcome to this beautifully renovated 2 bedroom 2 bath ocean view condo in the desirable Windward Passa...
- 2 Beds
- 2 Baths
- 202510726 MLS
- FS - Fee Simple Tenure
- Windward Passage Bldg.
- 120 DOM
Welcome to this rarely available residence in Gardenia Manor in the heart of desirable Kailua! This 2 bedroom, 2 bath, 2 side-by-side covered parking is located in a priv...
- 2 Beds
- 2 Baths
- 202507248 MLS
- FS - Fee Simple Tenure
- Gardenia Manor Bldg.
- 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
Highly prized and much sought after, a rare spacious home in K.M.; 3-bedroom, 2-bathrooms offer a perfect blend of contemporary comfort & style. 1,811 sf interior living ...
- 3 Beds
- 2 Baths
- 202506077 MLS
- FS - Fee Simple Tenure
- Ka Malanai At Kailua Bldg.
- 37 DOM
Welcome home to beautiful Kukilakila on Enchanted Lake with its meticulously maintained grounds, lakefront views, boat dock, walking paths, exercise room, recreation area...
- 2 Beds
- 2 Baths
- 202504589 MLS
- FS - Fee Simple Tenure
- Kukilakila Bldg.
- 21 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
Kailua Beachside Villa. Step inside the grand entrance with a sweeping Koa staircase, lava rock fountain and panoramic views of Kailua Bay. Awake every day to epic sunris...
- 6 Beds
- 7 Baths
- 202504677 MLS
- FS - Fee Simple Tenure
- 28 DOM
Lowest Priced 3 bed/2 bath in Kailua Beautifully refreshed ground floor 3-bed, 2-bath in highly sought-after Windward Cove, a secure gated community located just 1 mil...
- 3 Beds
- 2 Baths
- 202504776 MLS
- FS - Fee Simple Tenure
- Windward Cove Bldg.
- 230 DOM
Mid-Century Modern luxury seamlessly blends with island living, in Kailua's desirable Kaimalino neighborhood. This beautifully remodeled single-level home, with attached ...
- 4 Beds
- 3 Baths
- 202502693 MLS
- FS - Fee Simple Tenure
- 49 DOM
As soon as you drive up and see the wide, grassy frontage with a charming trellised entrance, you can already imagine calling this "home". This classic Kailua residence e...
- 3 Beds
- 2 Baths
- 202501808 MLS
- FS - Fee Simple Tenure
- 83 DOM
Discover the perfect blend of island elegance and modern updates in this 3-bedroom + den, 2.5 bathroom end unit townhome, located in Kailua's sought after Bluestone commu...
- 3 Beds
- 3 Baths
- 202502414 MLS
- FS - Fee Simple Tenure
- Bluestone Bldg.
- 114 DOM
Seller is motivated to get this SOLD! Bring in an offer! Welcome to this charming single level 3-bed, 2-bath home located in the highly desirable Ka Malanai Community in...
- 3 Beds
- 2 Baths
- 202501471 MLS
- FS - Fee Simple Tenure
- Ka Malanai At Kailua Bldg.
- 134 DOM
Immaculate condition with new kitchen and baths , new interior paint, new laminated wood floor thru-out for easy maintenance. Excellent location with Koolau and Olomana ...
- 2 Beds
- 2 Baths
- 202427844 MLS
- FS - Fee Simple Tenure
- Koolau Vista Bldg.
- 39 DOM
$100,000 Price Improvement! Welcome to the Pinnacle of Island Living! Discover the ultimate retreat in this luxurious Kailua home, fully renovated in 2024 & nestled on an...
- 5 Beds
- 3 Baths
- 202426409 MLS
- FS - Fee Simple Tenure
- 152 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
Nestled in the heart of Kailua Town, Windward Harbour presents an unparalleled opportunity to experience the island lifestyle, marrying comfort, elegance, and convenience...
- 3 Beds
- 2 Baths
- 202316891 MLS
- FS - Fee Simple Tenure
- Windward Harbour Bldg.
- 118 DOM
Large, Efficient Kailua Floor Plan - Your home under a mile of Kailua Beach. Closer yet to shopping, restaurants, school and recreational areas. 3 bedrooms / 2 full baths...
- 3 Beds
- 3 Baths
- 202409334 MLS
- FS - Fee Simple Tenure
- Gardenia Manor Bldg.
- 24 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 Room in Kailua, HI
An editorially curated view of every active homes with guest room listing in Kailua, HI. Updated in real time from the local MLS, presented without the noise.
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