Surf Bungalows To Beachside Mansions: A Look At 5 Quintessential Hawaii Retreats

Often regarded as a 'paradise,' Hawaii is home to some of the most desirable real estate in the world. (Hawaii Life)

Envision a life in paradise, where every day is a sun-kissed dream. Imagine residing in quaint surf town cottages or luxurious beachfront villas on the Hawaiian Islands, each offering unique charm. Whether you’re seeking a tranquil retreat or a vacation haven, these five enchanting homes in Hawaii are ready to welcome you into a new chapter of serene living.

A wide one story house with fields and a mountain in the background.

Wake up each morning to bi-coastal and neighboring island views. (Hawaii Life)

Custom Maui Home

This three-bedroom, three-bathroom custom Maui home boasts bi-coastal ocean and neighboring island views. It is the first time this nearly 3,000-square-foot home is on the market. Nestled on the slopes of Haleakala in the gorgeous Kula countryside, the estate spans 10 acres of organic property. It is the ideal place for anyone interested in a holistic lifestyle of organic farming and sustainable living. The home features strong concrete walls and a spacious four-car garage. You will find a chef’s kitchen with large pantry, as well as dual primary suites. The home is equipped with massive pocket sliding doors to take in the breathtaking views. Central air conditioning and heat promote comfort, and the fully fenced property is completely private.

The property is co-listed with Josh Jerman and Tim Stice of Hawaii Life.

A one story beach house at dusk behind a patio with a table.

This incredible property is on the market for the first time in 20 years. (Hawaii Life)

Crown Jewel of the North Shore

Available for the first time in over 20 years, this three-bedroom, two-bathroom beachfront home in the Oahu Kawela Bay gated community is a rare opportunity. There are only 11 beachfront homes in the community. The “crown jewel” of the North Shore, this home has an outdoor shower and surfboard storage. It is safe to swim in the bay 365 days a year, making this property ideal for the surf and swim enthusiast. The property is just a short walk to the excellent Palmer Golf Course and also has access to plenty of hiking and biking trails. This private oasis awaits you.

The home is co-listed with Sean F Ginella and John J Climaldi of Hawaii Life.

A Hawaiian 2-story house surrounded by tropical plants.

This stunning home is surrounded by tropical foliage and overlooks the Wailea Golf Course. (Hawaii Life)

Gorgeous Wailea Fairway Villa

Having undergone a full remodel in 2022, this three-bedroom, three-bathroom Maui villa features unobstructed views of the ocean and sunsets. The kitchen and bathrooms feature pristine quartz countertops and custom cabinets. The open kitchen layout is spacious and features a kitchen island with a waterfall edge. Enjoy top-of-the-line kitchen appliances to create your favorite meal and enjoy with a stunning view. The primary bedroom has a huge walk-in closet, and you will find gorgeous ceramic tile flooring throughout the villa. There are four split AC units for optimal comfort. The villa community features amenities such as a pool, spa, clubhouse, fitness area and built-in BBQ grills.

The villa is listed with Leslie Mackenzie Smith of Hawaii Life.

A sitting area with a view to a lush green yard, palm trees, and a blue ocean.

Unobstructed ocean views await you at 4850 Makena Alanui Road. (Hawaii Life)

Makena Surf Condo

Nestled on top of a hill overlooking Po’olenalena Beach in Maui, you will find this elegantly renovated two-bedroom, two-bathroom condo with incredible ocean views. Upon entry, the home impresses with the soaring ceilings, which reach over 10 feet tall. Central air conditioning will make sure you never overheat. The expanded lanai features sliding doors that are flush to the floor, promoting effortless indoor/outdoor living. Enjoy onsite amenities such as two pools, tennis courts, pickleball courts and a fitness center.

The condo is co-listed with Jeff Simon and Josh Jerman of Hawaii Life.

A clean, white house with surfboards and a nice green yard.

This home is a rare opportunity to own property in the iconic surf town of Hanalei. (Hawaii Life)

Surf Town Treasure

In the iconic surfing town of Hanalei is this remarkable four-bedroom, three-and-a-half bathroom home. The beach house comes with a vacant riverfront lot, which is open and ready for your to build your dream guest house. The beach house boasts nearly 3,000 square feet of living space, and is a surfer’s dream with an outdoor shower and garage for storage. Relax on the second-floor decks with a cup of coffee as you watch the sunrise, or enjoy the Seabreeze on the ground floor lanais. The home has refinished hardwood floors and granite countertops and new appliances in the kitchen. Create the estate of your dreams in Hanalei.

The residence is listed with Neal Norman of Hawaii Life.

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Nina Concepción is a Latina actor, writer, and Upright Citizens Brigade performer in Los Angeles. Her UCB credits include being a member of the house team "Elefante," Harold night, and numerous sketch shows. Nina's horror-comedy short film, "No Thank You," was an official selection of the 2021 Los Angeles Latino Film Festival. She is also the co-writer and star of "Schmotts," an indie award-winning comedy series.

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