Your Hawai’i Life Maui Vacation Rental Opportunity Guide: 6 Maui Vacation Rental Complexes to Keep on Your Radar

For millions of visitors each year, Maui is the premier destination for experiencing the extraordinary appeal of Hawaiʻi. With its alluring blend of lively beachside towns and striking natural beauty, the island retains a distinctive character all its own—and repeatedly tops the list when it comes to the best islands in the world.

Second to only the Big Island in area (at 735 square miles), Maui is home to a towering 10,000-foot volcano, verdant valleys, magnificent rainforests, and sun-soaked beaches. These remarkable features, along with world-class golf, shopping, and dining, make it the #1 choice for discerning vacationers and homeowners.

Stretching 48 miles from east to west and 26 miles from north to south, Maui is easily navigated in about 2.5 hours by car. Major roadways like Honoapiʻilani Highway, Piʻilani Highway, and Hāna Highway connect the island, providing convenient access to its most sought-after destinations.

Water sports like surfing, windsurfing, kiting, stand-up paddling, and kayaking are widely popular on Maui, and coral reefs running along many of the island’s southern and western shorelines create protected areas for swimming and snorkeling. Thousands of humpback whales also travel through the channel along Maui’s south and west shores each winter, making it the ultimate whale-watching location in the Hawaiian Islands.

The draw of the Valley Isle is not only in its raw beauty, but in the unparalleled charm of its communities. Two regions in particular offer an impressive variety of real estate opportunities in the form of vacation rental properties.

South Maui includes Kīhei and Wailea. With their agreeable climate, abundant sunshine, stunning beaches, and excellent location, these vibrant and scenic oceanfront towns attract tourists and locals alike.

West Maui includes Kāʻanapali, Lahaina, Kapalua, Nāpili, Kahana, and Honokowai. This region experiences a perfect balance of sun and rainfall, creating lush surroundings and picturesque coastal drives. The area is known for its resort towns, rich history, and the island’s most spectacular sunset and neighbor island views.

Standout South Maui Vacation Rental Complexes

The Hoʻolei condominiums embody refined island living, with rare 3-bedroom/3.5-bath residences directly across Wailea Alanui Drive from the Grand Wailea Resort and Wailea Beach. Immaculately maintained tropical landscaping surrounds private drives and elegant two-story condominiums. The complex is set apart by its sandy-entry lagoon-style pool and close proximity to the Wailea Golf Club’s three renowned courses, as well as fabulous shopping and dining possibilities at the Shops at Wailea.

The Mana Kai likewise impresses with incredible ocean views and direct access to Keawakapu, one of Maui’s most enjoyable options for long beach walks. The upscale complex boasts another rare find: 2-bed/2-bath floor plans with lockout features. This unique design allows owners to rent units out to two separate groups at a time, one side as a hotel room, and one side as a 1-bed/1-bath condo.

Ideally situated between Kamaole Beach Parks I and II in south Kīhei, Royal Mauian consists of 106 condominium homes in a lovely six-story community. Its 2- and 3-bedroom floor plans and rooftop garden with panoramic ocean and mountain views are just the beginning of a long list of advantageous features. Its enviable location provides ready access to every amenity in both Kīhei and Wailea.

Menehune Shores is an oceanfront condominium community with quick access to Maui’s longest stretch of sand, Sugar Beach. This six-story complex wows guests with attractive ocean-facing units, a heated oceanfront pool, and dazzling sunset and outer island views. Just steps away, Kalepolepo Beach Park and fishponds offer a peaceful haven for some of the most enjoyable swimming on the southern shore.

Noteworthy West Maui Vacation Rental Complexes

Shifting the spotlight to West Maui, Honua Kai consists of two ocean-facing towers and neighboring condominium residences on famed Kāʻanapali Beach. Among the newer complexes on the island, the Hokulani and Kunea towers were developed in 2008 and feature first-rate amenities like tropical pools with waterfalls and caves, a fitness center, and an on-site restaurant and general store. The adjacent upscale community of Luana Gardens boast desirable 3-bedroom/3-bathroom villas set within lush landscaping.

Overlooking breathtaking Kapalua Bay, Montage Kapalua Bay is an iconic destination complete with an ocean-view infinity pool, gorgeous grounds, and plentiful onsite amenities. Montage distinguishes itself through carefully crafted cultural, culinary, and recreational experiences tailored to guests. Its proximity to golf courses and ocean activities allows visitors to stay close while fully experiencing Maui’s magic.

Stay Tuned to Our Blog

In upcoming articles, we offer a deep dive into each of these exceptional complexes, providing comprehensive details on their unique vacation rental properties and how they compare to others on the island.

In the meantime, Inquire to learn more about active and potential units for sale in these complexes. At Hawaiʻi Life, we have Realtors who specialize in working with clients focused on second homes and vacation rentals. These agents have decades of experience, in-depth on-island knowledge, and access to critical data points that are necessary to make well-informed choices.

Our in-house vacation rental management division generates nearly $30M in revenue and upwards of 74,000 bookings annually. Together with our Hawaiʻi Life agents, they make us the best-equipped Hawaiʻi real estate firm to assist vacation rental clients.