Wailuku Homes with Short Term Rental Allowed

Wailuku Homes with Short Term Rental Allowed

Welcome to Wailuku, a charming town nestled in the heart of Maui County, Hawaii. Known for its rich history and vibrant culture, Wailuku is the perfect blend of old-world charm and modern convenience. As the county seat of Maui, this picturesque town boasts stunning views of the West Maui Mountains and is just a stone's throw away from the beautiful beaches and lush landscapes that make Maui a world-renowned destination.

Wailuku is a hub for local arts and culture, with historical landmarks, galleries, and theaters that reflect the island's unique heritage. Stroll through the quaint streets lined with local shops and eateries, where you can savor the flavors of authentic Hawaiian cuisine or pick up a handcrafted souvenir. The town is also home to the iconic Iao Valley State Park, where you can explore lush hiking trails and witness the majestic Iao Needle, a natural rock formation that stands as a testament to the island's geological beauty.

For those considering a home in this idyllic location, Wailuku offers a fantastic opportunity for short-term rentals. With its appealing climate and proximity to popular tourist attractions, homes in Wailuku are not only a great place to live but also a lucrative investment for short-term rental options. Imagine hosting guests from around the world in a cozy retreat that captures the essence of Hawaiian living.

Whether you're drawn to Wailuku for its vibrant community or its investment potential, this charming town has something for everyone. Embrace the Aloha spirit and discover your dream home in Wailuku today!

Newest Wailuku Homes with Short Term Rental Allowed

$899,000
2 Beds ⋅ 2 Baths ⋅ 410311 MLS ⋅ Leasehold Tenure ⋅ Kanai A Nalu BLDG.
Your front row seat to paradise and oceanfront luxury awaits at Kanai A Nalu #417! This exceptional 4th-floor 2-bedroom, 2-bath residence offers breathtaking panoramic views of the Pacific Ocean, Sugar Beach, Haleakala, and spectacular year-round sunrises. Extensively remodeled with over $200,000 in premium upgrades, this turnkey condominium showcases an open-concept design with a beautifully appointed kitchen, quality cabinetry, stone countertops, stainless steel appliances, luxury flooring, designer lighting, and tastefully remodeled bathrooms. Enjoy year-round comfort with three split-system A/C units serving the living area and both bedrooms. The spacious oceanfront lanai is the perfect place to relax while watching humpback whales (seasonal), sea turtles, and the soothing waves along Maui's shoreline. Kanai A Nalu is a heavily booked short-term vacation rental, making this an outstanding opportunity for both personal enjoyment and investment potential. Ideally located on Maui's longest white sand beach, the complex features a heated oceanfront pool, BBQ area, elevator, lush tropical landscaping, and convenient parking, all just minutes from Ma?alaea Harbor, restaurants, shops, golf, Kahului Airport, Wailea, and West Maui. Offered fully furnished and move-in ready. This is a leasehold property.

250 Hauoli St Unit 417, Wailuku

Listing courtesy of Century 21 Island Homes.

$599,000
1 Beds ⋅ 1 Baths ⋅ 409767 MLS ⋅ Fee Simple Tenure ⋅ Island Sands BLDG.
Rarely does a one bedroom residence on Maui's South Shore offer this kind of presence. Positioned on the third floor of Island Sands, this beautifully appointed oceanfront condominium opens to sweeping Pacific views that stretch from the palms framing the lanai all the way to the neighbor islands on the horizon. The interior is warm and well finished throughout, with wood look flooring, white cabinetry, stainless steel appliances, and coastal themed artwork and decor that give the space a genuine sense of place. The generous lanai is oriented to capture unobstructed ocean and palm tree views and serves as the true heart of the home. Offered turn key and move in ready, this unit is currently active in a successful vacation rental program. In-unit washer and dryer, dishwasher, air conditioning, community pool, elevator access, and one deeded parking stall complete this exceptional offering in one of South Maui's most sought after oceanfront communities.

150 Hauoli St Unit 303, Wailuku

Listing courtesy of Sunny Maui Vacations.

$975,000
2 Beds ⋅ 2 Baths ⋅ 409309 MLS ⋅ Fee Simple Tenure ⋅ Lauloa BLDG.
Lauloa 209 — oceanfront, fully renovated, and ready to go. Step inside to wide-plank floors, solid wood cabinetry, new countertops, and split A/C throughout. The living area opens to a lanai with unobstructed views across Ma'alaea Bay to Haleakala. Primary suite has an ensuite bath and ocean views. The building sits right on the water with a pool, lawn, and easy access to Ma'alaea Harbor, Sugar Beach, and nearby restaurants. Turnkey condition with proven rental history. Second home, investment, or both — this one checks the boxes.

100 Hauoli St Unit 209, Wailuku

Listing courtesy of Luxe Maui Properties LLC.

$999,000
2 Beds ⋅ 2 Baths ⋅ 409251 MLS ⋅ Fee Simple Tenure ⋅ Maalaea Banyans BLDG.
Welcome to Unit 412 at Maalea Banyans—an inviting 2 Bedroom 2 Bathroom oceanfront retreat nestled in the heart of Maalaea. This well-positioned condo offers breathtaking views of the Pacific, where you can enjoy stunning sunrises, seasonal whale watching, and the soothing sound of waves right from your private lanai. Inside, the unit features a bright and airy layout designed to maximize natural light and coastal breezes. The open-concept living and dining area flows seamlessly, creating a relaxed island atmosphere perfect for both everyday living and entertaining. Large windows and sliding glass doors bring the outdoors in, enhancing the tranquil beachfront experience. Convenience is a standout feature of this location. Maalaea Harbor is just moments away, offering easy access to world-class snorkeling, boating excursions, and waterfront dining. You’re centrally located between Lahaina and Kihei, making it simple to explore all that Maui has to offer—from pristine beaches and golf courses to shopping and local markets. The nearby Maui Ocean Center and quick access to major roadways add to the ease and enjoyment of daily life.Contact us today for your own private tour.

190 Hauoli Rd Unit 412, Wailuku

Listing courtesy of Keller Williams Realty Maui-Ki.

$799,000
2 Beds ⋅ 2 Baths ⋅ 409219 MLS ⋅ Fee Simple Tenure ⋅ Island Sands BLDG.
Highly sought-after oceanfront top-floor condo in one of Maalaea’s most desirable fee simple buildings. Enjoy spectacular ocean and outer island views from your private covered lanai. This upgraded residence features a beautifully remodeled kitchen with granite countertops, an updated bathroom with a modern vanity and walk-in tiled shower, and tile flooring throughout.The spacious primary bedroom has been thoughtfully reconfigured to create an additional flex space - perfect for a dining area, home office, or extra sleeping quarters. Offered fully furnished, this unit includes one assigned parking stall and is ideally located just a short stroll to the beach, Maalaea Harbor, the Maui Ocean Center, shops, and restaurants.Community amenities include an oceanfront swimming pool and barbecue area.

150 Hauoli St Unit 602, Wailuku

Listing courtesy of Hawaii Life (W).

$549,000
1 Beds ⋅ 1 Baths ⋅ 409220 MLS ⋅ Fee Simple Tenure ⋅ Island Sands BLDG.
Located in one of Maalaea’s most desirable fee simple buildings, Island Sands 103 is a wonderful ground-floor unit offering beautiful ocean views and easy access to the oceanfront pool and barbecue area. This updated condo features a remodeled kitchen with granite countertops and a walk-in tiled shower. The living room includes a wall-mounted Murphy bed, providing flexible additional sleeping space. Tile flooring throughout extends seamlessly to the spacious lanai, creating ideal indoor-outdoor living. Offered fully furnished, this unit includes one assigned parking stall and is ideally situated just a short walk to the beach, Maalaea Harbor, the Maui Ocean Center, shops, and restaurants.

150 Hauoli St Unit 103, Wailuku

Listing courtesy of Hawaii Life (W).

$249,900
1 Beds ⋅ 1 Baths ⋅ 408893 MLS ⋅ Leasehold Tenure ⋅ Milowai BLDG.
Rare Ground-Floor Direct Oceanfront! Experience the ultimate Maui lifestyle in Milowai 106. This beautifully remodeled 1BR/1BA unit sits just feet from the water’s edge—walk directly from your private lanai onto the lush lawn to watch whales, sea turtles, and the famous “Freight Trains” surf break. Fully Remodeled: Modern kitchen with granite countertops, stainless appliances, tile flooring, and A/C for maximum comfort. Fully furnished and active as a successful short-term rental. Includes in-unit washer/dryer. The property is leasehold. The Special Assessment for the Sea Wall has been PAID IN FULL by the seller,providing immediate value and lower monthly overhead for the new owner.

50 Hauoli St Unit 106, Wailuku

Listing courtesy of Luxe Maui Properties LLC.

$275,000
1 Beds ⋅ 1 Baths ⋅ 408892 MLS ⋅ Leasehold Tenure ⋅ Hono Kai BLDG.
The lowest-priced oceanfront opportunity in Ma'alaea. Front-row seats to Ma'alaea Bay where humpback whales breach in winter, surfers glide across the waves, and the Pacific becomes part of your everyday view. This second-floor unit at Hono Kai is positioned directly on the shoreline within one of Maui’s most intimate oceanfront communities, just 46 units across a lush one-acre property. Enjoy morning coffee from your private lanai while taking in panoramic ocean views and cooling trade winds. Walk to Ma'alaea Harbor, Maui Ocean Center, waterfront dining, shops, and Haycraft Park. Just outside your door, access miles of sandy shoreline stretching toward Kihei. The unit has been beautifully updated with a remodeled kitchen and bath, quality finishes, and a clean coastal aesthetic. Offered fully furnished vacation rental with excellent guest reviews. Hono Kai is pet friendly, and maintenance fees include water, trash, cable, internet, exterior insurance, landscaping, and pest control. Ideal as a full-time residence, Maui getaway, or income-producing investment. This is a leasehold property.

280 Hauoli St Unit B-17, Wailuku

Listing courtesy of Emerald Club Realty Inc.

$799,000
2 Beds ⋅ 2 Baths ⋅ 408473 MLS ⋅ Fee Simple Tenure ⋅ Hono Kai BLDG.
This beautiful, 2 bedroom, 2 bathroom condo has a bonus loft, suitable as an extra sleeping area or office, and sits directly in front of the longest beach on Maui. Amazing ocean and mountain views from every room. Ideal spot for whale watching, ocean sports, and surfing, as this is right next to the world famous "Freight Train" wave break. Short distance to Maui Ocean Center Aquarium, restaurants, shops, miniature golf, Haycraft Beach Park, and Maalaea Harbor, with Pacific Whale Foundation, activities, snorkel/dive tours to Molokini, the Lanai Ferry, and much more. The unit has many upgrades, including granite counters, travertine floors, and 16 ft high ocean-facing windows, allowing you to enjoy endless views and sunshine. Sold fully furnished and turn-key, this is a successful vacation rental. Visitors give this unit 9.8 stars on VRBO and sellers will transfer any existing reservations to new owner. Easy access to Lahaina, Kihei, and Kahului Airport makes this an excellent full or part-time residence, or investment opportunity. If you are looking for a well-appointed Maalaea condo, this is it!

280 Hauoli St Unit 8B, Wailuku

Listing courtesy of Coldwell Banker Island Prop-Ku.

$798,000
2 Beds ⋅ 2 Baths ⋅ 408450 MLS ⋅ Fee Simple Tenure ⋅ Island Sands BLDG.
Enjoy island living in the heart of Maalaea in this beautifully renovated 2-bedroom, 2-bathroom condo with stunning ocean views. The living room, kitchen, main lanai, and primary bedroom all capture expansive views of the Pacific, with the primary suite also featuring its own private lanai. Located in a direct oceanfront complex, this property offers front-row seats to turtle activity along the shoreline and seasonal whale watching. The unit has been fully remodeled, including a brand-new kitchen and updated bathrooms, fresh interior paint, and tasteful furnishings throughout. The open and functional floor plan is complemented by air conditioning, in-unit washer and dryer, high-speed internet, and smart TVs. One assigned parking stall is included. Conveniently situated within walking distance to Maalaea Harbor, restaurants, and shops, this centrally located condo offers easy access to boating, dining, and island activities. Community amenities include an oceanfront swimming pool and BBQ area, ideal for enjoying Maui’s outdoor lifestyle.

150 Hauoli St Unit 300, Wailuku

Listing courtesy of Whalers Investment Group LLC.

$375,000
1 Beds ⋅ 1 Baths ⋅ 408332 MLS ⋅ Fee Simple Tenure ⋅ Hono Kai BLDG.
Hono Kai B15 is a beautifully furnished and well-appointed second-floor 1-bedroom, 1-bath condo offering tropical views from a private lanai. Recent upgrades include fresh interior paint, new ceiling fans, and custom mahogany shoji doors. Hono Kai is a quaint beachfront property just steps from a six-mile stretch of sandy beach. Enjoy ocean and outer-island views from the oceanfront pool and barbecue area. Located in Maalaea Bay near shops, restaurants, and attractions—walk to the Maui Ocean Center, Maalaea Harbor, and nearby activities including mini golf. Convenient access to Lahaina, Kihei, and Kahului Airport makes this an excellent full-time residence, second home, or investment opportunity.

280 Hauoli St Unit B-15, Wailuku

Listing courtesy of Hawaii Life (W).

$625,000
1 Beds ⋅ 1 Baths ⋅ 408191 MLS ⋅ Fee Simple Tenure ⋅ Island Sands BLDG.
Wake up to front-row ocean views at Island Sands 110, a well-maintained ground-floor condo designed for effortless island living. Take in the scenery from the living room or step out to the lanai - either way, the view is stunning. This 1-bedroom, 1-bath condo has a functional layout with a king-size bed and a queen-size sofa sleeper, ideal for accommodating guests. It includes split A/C, an assigned parking spot, and an in-unit washer and dryer for added convenience. Residents can unwind with resort-style amenities, including a pool and BBQ area. Ideally located in Maalaea, the condo offers convenient access to everything the island has to experience. Spend the day around Maalaea exploring the Maui Ocean Center, or walk to the nearby harbor where you can experience one of the many whale-watching and snorkeling boat tours. World-class golf, hiking trails, and some of Maui's best surf spots are just a short drive away. A variety of nearby restaurants are available to satisfy every craving, making this condo the perfect base for both adventure and relaxation on the island.

150 Hauoli St Unit 110, Wailuku

Listing courtesy of Hawaii Life (W).

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