Kaanapali Luxury Vacation Rentals, Beachfront Homes & Villas

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From $10,000.00 / daily
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Kaanapali_Kahala

Kaanapali Kahala*

Lahaina

Beds: 8   Baths: 9.5   Sleeps: 16
From $4,975.00 / daily
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Hawaiiana_Hale

Hawaiiana Hale*

Lahaina

Beds: 4   Baths: 5   Sleeps: 8
From $2,350.00 / daily
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Sea_Shells_Beach_House

Sea Shells Beach House on Ka`anapali Beach

Kaanapali

Beds: 3   Baths: 3.5   Sleeps: 6
From $1,425.00 / daily
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Rainbow_Hale_Estate

Rainbow Hale Estate*

Lahaina

Beds: 4   Baths: 3.5   Sleeps: 8
From $325.00 / daily
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Kaanapali_Royal_A201_MAUI

Kaanapali Royal #A201 (MAUI)

Lahaina

Beds: 2   Baths: 2   Sleeps: 6

Kaanapali: Maui’s Well-Rounded Resort Community

Former sugar plantation land converted into a resort community in the early 1960s, Kaanapali offers an ideal vacation destination on Maui’s northwest coast. With the West Maui Mountains as a backdrop, the area features panoramic views of the neighbor islands of Lanai and Molokai, along with stunning sunsets year-round. Perhaps no other region in the Hawaiian Islands provides more in the way of beaches, dining, shopping, water sports/adventures, and golf while retaining such a charming old-Hawaii feel.

Visitors seeking long stretches of white sand will find exactly what they hoped for in Kaanapali Beach and Kahekili Beach. Separating the two is Black Rock, known to ancient Hawaiians as Pu’u Keka’a, the sacred location where the souls of the deceased would leap from the physical world into the spirit world. Now known for its exceptional snorkeling, Black Rock also presents an opportunity for daring locals and tourists to try cliff jumping.

 

An oceanfront path spanning the length of Kaanapali Beach creates the perfect setting for a sunset stroll, evening cocktail, or dinner at an open-air restaurant, many of which also have live local music. In particular, Whaler’s Village provides several fantastic options, including Monkeypod Kitchen (home of the best Mai Tai on the island!), Leilani’s on the Beach and Hula Grill. Free hula performances also take place at Whaler’s Village every Wednesday and Saturday at 7 p.m.

Visitors will also find the picturesque port town of Lahaina just 10 minutes south of Kaanapali. Rich in history as the original capital of the Kingdom of Hawaii and the former whaling capital of the Pacific, this bustling area now houses countless restaurants, shops, and art galleries. Paia Fish Market, on Lahaina’s Front Street, has excellent casual cuisine (including fish tacos, salads, and sandwiches), while oceanfront Kimo’s and Koa’s boast fabulous seafood, and Fleetwood’s (owned by Maui resident Mick Fleetwood, of Fleetwood Mac) features fine dining and a rooftop bar with an incredible sunset view. For a truly authentic Hawaiian experience, visitors may also enjoy a trip to the Old Lahaina Luau (at the north end of Front Street) or the Feast at Lele (at the south end).

Numerous snorkeling excursions (often north to Honolua Bay or south to Turtle Town), whale-watching trips, and sunset sails/dinner cruises leave from either Kaanapali or Lahaina. For those feeling adventurous, the area also offers opportunities to take a surfing lesson , rent a jet ski, or book a parasailing excursion. And of course, there are the two breathtaking Kaanapali Golf Courses and, slightly farther north, the two jaw-dropping Kapalua courses (including the Plantation Course, home to the PGA Tour’s Tournament of Champions).

Speaking of local events, following Kapalua’s Tournament of Champions in early January each year, Lahaina hosts a Chinese New Year Celebration each February, and Kaanapali Beach Hotel hosts the Maui Steel Guitar Festival each April. The scenic Maui Marathon’s half-marathon, 10K, and 5K begin and end in Kaanapali every October, the same month of the annual XTERRA World Championship off-road triathlon in Kaanapali. A Halloween parade and celebration in Lahaina have come to be known as the Mardi Gras of the Pacific, and the Maui Invitational college basketball tournament takes place in the Lahaina Civic Center each year in late November. Year-round, Lahaina also holds a town party every Friday, closing Front Street to car traffic to make room for food vendors, live music, arts and crafts, and other local goods.