Kailua Homes with Guest Parking Features

Welcome to Kailua, a picturesque gem nestled on the eastern coast of Oahu, Hawaii. Known for its stunning beaches, lush landscapes, and vibrant community, Kailua offers a unique blend of island charm and modern conveniences. With its turquoise waters and soft sandy shores, beaches like Lanikai and Kailua Beach Park are perfect for sunbathing, kayaking, and paddleboarding, making it a haven for outdoor enthusiasts.

Kailua is not just about breathtaking views; it’s a community that fosters a relaxed lifestyle while being just a short drive from the bustling city of Honolulu. The town boasts an array of local shops, delightful eateries, and cultural experiences, ensuring that residents enjoy a well-rounded lifestyle. The warm, welcoming atmosphere of Kailua makes it an ideal place for families, retirees, and anyone looking to embrace the beauty of island living.

For those considering a home in this idyllic location, many properties come with guest parking features, making entertaining family and friends a breeze. Imagine hosting a sunset barbecue or a cozy gathering after a day at the beach, knowing that your guests have a convenient place to park. Homes with this feature not only enhance your hosting capabilities but also add an element of comfort and convenience to your daily life.

Whether you’re seeking a serene retreat or an active lifestyle, Kailua offers a perfect balance. Explore the beautiful homes available, complete with guest parking, and discover how this enchanting island town can be the backdrop to your next chapter. Welcome home to Kailua, where paradise awaits!

Newest Kailua Homes with Guest Parking Features

$550,000

2 Beds ⋅ 2 Baths ⋅ 202615437 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM ⋅ Poinciana Manor BLDG.

Best value in Poinciana Manor! Bright and breezy top-floor end unit featuring peaceful garden views, cathedral ceiling, and two private lanais. This unit includes two covered parking stalls and a remodeled kitchen, while offering the opportunity to customize the rest to your personal style. Conveniently located in the heart of Kailua, close to shopping, dining, schools, and beaches. Poinciana Manor offers beautifully maintained grounds with a pond, water features, swimming pool, recreation and BBQ areas, plus guest parking. Property is being sold AS-IS. Unit is currently unstaged and includes no appliances except for a dishwasher. Photos shown are from the prior listing.

1015 Aoloa Place Unit 437, Kailua

$1,495,000

3 Beds ⋅ 3 Baths ⋅ 202614708 MLS ⋅ FS - Fee Simple Tenure ⋅ 11 DOM ⋅ Bluestone BLDG.

Bluestone's Kamahele Townhome - under $1.5M! Welcome to Bluestone, one of Kailua’s most private and prestigious gated communities. Set on nearly 50 acres of lush grounds fronting Mid-Pacific Country Club and surrounded by preservation land, this 3-bedroom, 2.5-bath townhome offers rare privacy, sweeping golf course, Ko‘olau mountain, and sunset views, plus an attached full-size garage and driveway parking for two additional vehicles. Three covered lanais capture cooling trade winds and provide seamless indoor-outdoor living. Bluestone residents enjoy resort-style amenities including a pool, whirlpool, BBQ areas, recreation spaces, tennis/pickleball courts, sauna, and gated security with patrol. Ideally located in the hills of Kailua, just minutes from Lanikai Beach and the Pillbox hike, this is a rare opportunity to own a townhome style with attached garage in the prestigious community of Bluestone at $1,495,000 — one of the few under $1.5M. Come and see what the Bluestone community has to offer! Sold As-Is. Furniture is negotiable.

1150B Kamahele Street Unit #3002, Kailua

$990,000

2 Beds ⋅ 2 Baths ⋅ 202614646 MLS ⋅ FS - Fee Simple Tenure ⋅ 12 DOM ⋅ Windward Passage BLDG.

Experience the best of the Kailua lifestyle in this upgraded + rarely available Windward Passage residence with endless ocean views and the most desirable floor plan. Located in the heart of Kailua, this home is moments away from the most iconic destinations—from the clear blue waters of Kailua + Lanikai beaches to the scenic Pillbox hike and golf courses. Plus the convenience of having Whole Foods, Target, Down to Earth, and endless dining options and boutiques just a short walk away. Originally a three-bedroom layout, one wall was removed to create more living area but is easily converted back if preferred. Enjoy endless views of the coastline from floor to ceiling windows perfectly framing the ocean views in every room, and start your mornings on the private lanai watching the sunrise over the Pacific. Well-maintained, pet-friendly community that feels like a private resort, featuring a full suite of amenities including a refreshing pool, fitness center, tennis + pickleball courts, racquetball courts, and dedicated racks for your bikes + surfboards. With an on-site manager and 24-hour security, enjoy luxury and peace of mind in one of Oahu’s most sought-after beach towns.

322 Aoloa Street Unit 1201, Kailua

$690,000

2 Beds ⋅ 2 Baths ⋅ 202614286 MLS ⋅ FS - Fee Simple Tenure ⋅ 15 DOM ⋅ Poinciana Manor BLDG.

Experience the best of Kailua living! This beautifully updated 959 sq ft unit offers a modern kitchen with updated cabinets & countertops, updated bathroom vanities, and stainless steel appliances. Enjoy the convenience of a full-size washer and dryer, fresh paint throughout, newly installed luxury vinyl plank flooring, contemporary light fixtures, and a brand-new ceiling fan. The unit also includes two side-by-side covered parking stalls and a spacious 266 sq ft lanai, providing added privacy with an exterior-facing view. Located in the heart of Kailua, you're just steps away from boutique shops, local restaurants, cafes, bookstores, grocery stores, and the world-renowned Kailua Beach. The complex boasts fantastic amenities such as a saltwater pool, BBQ areas, gazebos, a kids’ playground, a koi pond, bike/surfboard storage, guest parking, on-site security, and a resident manager. The complex is fully insured and pet-friendly making it an excellent place to call home!

1015 Aoloa Place Unit 247, Kailua

$645,000

1 Beds ⋅ 1 Baths ⋅ 202614387 MLS ⋅ FS - Fee Simple Tenure ⋅ 15 DOM ⋅ Windward Passage BLDG.

Rarely available prestigious penthouse unit at the top of Windward Passage! Floor to ceiling windows open to a panoramic view out over Enchanted Lake & down the majestic Koolau Mountain range. You can even enjoy the colors of the sunset as the sun sinks below the mountains in the evenings. The whole apartment opens to the view, and all that window space gives you a bright airy open feel that makes the unit seem even larger than it is. The kitchen & bathroom have been upgraded. The bathroom renovation included replacing the tub with a full-size shower & brand-new vinyl plank flooring was just installed throughout. Everything is ready for you to move in & enjoy! Add to this the resort style amenities that Windward Passage has to offer including tennis courts, pickleball, a racquetball court, swimming pool, whirlpool, BBQ areas, dog park, fitness center with saunas, storage areas for surfboards & bicycles & additional storage for each unit. Plus, a can't beat location right in Kailua Town with easy access to shopping, restaurants, the open markets and so much more with Kailua Beach just moments away. What more could you ask for? This is just what you've been waiting for!

322 Aoloa Street Unit PH8, Kailua

$1,650,000

2 Beds ⋅ 3 Baths ⋅ 202612833 MLS ⋅ FS - Fee Simple Tenure ⋅ 30 DOM ⋅ Bluestone BLDG.

Welcome to Bluestone – where island living meets everyday luxury! Picture yourself sipping your morning coffee or dining in the evening on your lanai while looking across acres of green and sunsets dipping behind the Ko'olau Mountain Range. Or waking up to catch a rainbow over the golf course from the comfort of bed. Maybe join a friend for a meal or round of golf at near-by Mid-Pacific Country Club. Or take advantage of the resort-like amenities that Bluestone has to offer such as tennis courts, pickle ball, salt-water pool, hot tub, sauna, or one of many other activities available to you nearby. It’s the Kailua lifestyle, beautiful Lanikai Beach, the open spaces and the scenic beauty that makes Bluestone such a fabulous place to live. Add to that list a lovely townhome in a gated community with stunning views and cooling breezes. Spacious, scenic, and serene, it’s a truly special place to call home.

1302 Kamahele Street Unit 2402, Kailua

$925,000

3 Beds ⋅ 2 Baths ⋅ 202608120 MLS ⋅ FS - Fee Simple Tenure ⋅ 72 DOM ⋅ Windward Harbour BLDG.

Wake up to breathtaking mountain views and end your day on your own private rooftop lanai. This rare, 3-bedroom 2-bathroom gem at Windward Harbor blends modern Kailua elegance with resort-style amenities. This is island living at its finest. From the floor-to-ceiling windows that bathe the open-concept of indoor and outdoor living space with a screened in lanai to enjoy the tropical water features and landscapes. The Primary Suite is located downstairs with a large walk in closet and shower and two bedrooms plus full bathroom upstairs. Enjoy two covered side by side parking right at the walk way for easy entry. Conveniently located in the heart of Kailua Beach Town, Whether you're strolling to Kailua Town for your morning coffee or hitting the sands of world-famous Kailua Beach, this isn't just a condo—it’s your personal sanctuary. Gated Community with amenities including an on-site manager, pool, jacuzzi, sauna, BBQ, car wash, Pickleball and Tennis courts. This is a pet-friendly building!

1030 Aoloa Place Unit 2/302B, Kailua

$619,000

2 Beds ⋅ 2 Baths ⋅ 202609776 MLS ⋅ FS - Fee Simple Tenure ⋅ 49 DOM ⋅ Poinciana Manor BLDG.

This Poinciana Manor unit is a spacious blank slate awaiting your personally chosen upgrades, on your timeline. Excellent location in the building, with views of the open courtyard, garden, and koi pond. Enjoy peace and quiet, the faint sound of birds, and a trickling fountain. The open, flowing layout has tropical terracotta tile from kitchen to dining to living to covered lanai to open lanai; the hallway and baths have same tile as well. Two covered parking stalls, storage closet in parking area, easy entry and elevator access, bike and surfboard storage, security, plenty guest parking, car wash area... all features of great convenience that enhance your everyday living! Lovely walking pathways, lush lawn courtyard, picnic areas, and nice pool round out the features to enjoy. Cabinets are original, offering more than adequate storage. The full-size washer/dryer and dishwasher are newer. This is a home to enjoy, experience, and feel everything out while you decide if you want to just decorate or remodel. Enjoy the beach-town lifestyle Kailua offers, a few blocks from beaches, dining, shopping, for an affordable price in a well-managed development. Seller is offering credits.

1015 Aoloa Place Unit 219, Kailua

$674,000

2 Beds ⋅ 2 Baths ⋅ 202611825 MLS ⋅ FS - Fee Simple Tenure ⋅ 53 DOM ⋅ Poinciana Manor BLDG.

New Price & Now Available with a 3.125% VA Assumable Interest Rate! – Incredible Value in the Heart of Kailua! Move-in ready and priced to sell, this 2-bedroom, 2-bath condo in Poinciana Manor offers the perfect blend of comfort, convenience, and island living. Enjoy luxury vinyl plank flooring throughout the main living areas, updated bathroom vanities and countertops, AC throughout, and a kitchen with stainless steel appliances. Relax on your private, covered lanai surrounded by bamboo landscaping with beautiful Ko'olau mountain views. Additional highlights include two side-by-side covered parking stalls, a dedicated storage locker, and in-unit washer/dryer. Just minutes from world-famous Kailua Beach, shopping, dining, and everything Kailua has to offer. Don't miss this opportunity to own one of Kailua's best values! (As of 8/5/26: 3.125% interest rate, $461,303.51 remaining balance, P&I: $2,491.42/month)

1015 Aoloa Place Unit 335, Kailua

$640,000

1 Beds ⋅ 1 Baths ⋅ 202611276 MLS ⋅ FS - Fee Simple Tenure ⋅ 54 DOM ⋅ Windward Passage BLDG.

Rare high-floor one-bedroom unit with breathtaking views of Enchanted Lake, the Ko'olau Mountains and Kailua Town. Remodeled in 2025 with vinyl luxury flooring throughout, along with updated appliances, cabinets, countertops, lighting, and fixtures. Light and bright, the unit features floor to-ceiling windows that showcase the expansive views. Evening views are spectacular with gorgeous colorful skies as the sun sets behind the mountains. No popcorn ceilings, two window A/C units, an in-unit washer and dryer, and one covered assigned parking stall. Amenities include a heated saltwater pool, spa, sauna, BBQ area, dog park, tennis and pickleball courts, guest parking, 24-hr. security, fitness center, EV charger on property, kayak and surfboard racks, plus storage. Conveniently located in the heart of Kailua, the building is close to Kailua Beach, Whole Foods, Target, restaurants, and shops. Pet-friendly and ideally situated to enjoy everything Kailua has to offer!

322 Aoloa Street Unit 1708, Kailua

$739,000

2 Beds ⋅ 2 Baths ⋅ 202611566 MLS ⋅ FS - Fee Simple Tenure ⋅ 56 DOM ⋅ Aikahi Gardens BLDG.

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 upgrades include finnished stairway to 2nd floor and wood flooring in living room. Unit is well maintained, light and airy. Close to KMCAS, Aikahi Elementary School and shopping center. Great access to H-3, Kailua Beach and all the stores and restaurantss in the Kailua area.

134 Noke Street Unit 602, Kailua

$1,450,000

3 Beds ⋅ 3 Baths ⋅ 202607704 MLS ⋅ FS - Fee Simple Tenure ⋅ 75 DOM ⋅ Windsurfer BLDG.

Experience the quintessential Kailua LIFESTYLE at The WINDSURFER, a boutique 10-unit townhome community situated directly across from Kailua Beach. LOCATION. This part of Kailua Beach has Oahu's BEST KITESURFING; it's heaven! The Windsurfers Unit #4 Is the Special Unit that sits right on the lily pond, a happy and serene spot to reflect the days activities. This RARELY AVAILABLE residence features a freshly painted interior, loft, new washer and dryer, and updated kitchen and bathrooms from a 2018 renovation. The versatile layout can accommodate either three bedrooms, or two bedrooms with a flex space and a half bath. The large tiled private patio offers many opportunities, entertaining, dining, outdoor living room and is has a lighted walk in storage closet for bikes, tools, and equipment. 2 reserved and excellent parking spaces right outside your door and guest parking is available for your friends. Most importantly ... Yes, PET FRIENDLY! Located just steps from world-class windsurfing, Kalapawai Market, and BUZZ'S Steakhouse, this serene retreat offers a welcome escape from the bustle of Honolulu. CALL today to learn all about the outstanding lifestyle at the Windsurfer!

445 Kawailoa Road Unit 4, Kailua

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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.