Wailea vs. Ka'anapali: Which Resort Area is Better?

Wailea vs. Kaanapali

Maui covers more than 727 square miles and is home to more than 164,000 people. The landscape is diverse with stunning beaches, tropical forests, volcanic formations, and numerous towns and small communities. As you plan your upcoming trip or plan for a purchase on Maui, you understandably want to be close to top-rated activities and hot spots.

West and South Maui are both popular destinations for visitors, and Wailea and Kaanapali in these regions are both brimming with things to do when you visit the island. Before choosing a specific Maui resort to stay at, a closer look at the differences between Wailea and Kaanapali can be very helpful.

Wailea: A Premier Maui Resort Community

Wailea Maui

Located on the southern side of the island, Wailea is home to top-rated resorts like Fairmont Kea Lani, Grand Wailea Waldorf Astoria, Four Seasons Maui, Wailea Beach Resort Marriott, and others. There are also numerous condos in Wailea and homes available for sale or rent.

Widely considered to be the most luxurious part of Maui, Wailea is home to several world-class beaches and offers amazing views of Molokini Crater from many vantage points. 

Outdoor Activities

South of Wailea, you can relax under the sun and take advantage of South Maui’s great weather at Makena Beach and Maluaka Beach. Just north of this resort community, you will find Keawakapu Beach. At Wailea beaches, you can enjoy whale watching, snorkeling, kayaking and sunbathing.

In some locations, surfing lessons for beginners and more advanced surfers are available.

Wailea offers you numerous other opportunities for relaxation and fun when you visit Maui. It is home to some of the island’s top golf courses. These include Wailea Golf Club, the Kea Lani Golf Course, and the Makena Golf and Beach Club.

You can admire amazing coastal views on the Wailea Coastal Walkway. This 1.5-mile walking path takes you by hibiscus trees and wildflowers between Polo Beach and Ulua Beach. The King's Highway Trail, which is also called the Hoapili Trail, takes you by impressive lava rock formations and historical sites. 

Is Wailea sunnier than Kaanapali?

Many visitors prefer Wailea over Kaanapali because of its weather. Wailea, located in the south,  experiences less rain than Kaanapali. However, Kaanapali's rainy season is typically from November to April, so during the rest of the year you shouldn't have much of a problem with rain. 

Cultural Experiences

Several luaus are available for an unforgettable cultural experience with dancing and local food, including the famed Grand Luau at Honua’ula.

Other opportunities for enjoying your time in Wailea include indulging in a spa treatment at a local resort, exploring the high-end Shops at Wailea, playing at the Wailea Tennis Club, touring Turtle Town, dining at the area's best restaurants and more.

There are numerous tours departing from Wailea and nearby Kihei. These include snorkeling trips to Molokini, the Road to Hana tour, sunset dinner cruises and whale-watching cruises. While visiting nearby Kihei, you can stroll along the Kealia Coastal Boardwalk at the Kealia Pond National Wildlife Refuge and learn about aquatic life at the Humpback Whale Sanctuary.

The state’s largest and most well-known craft brewery, the Maui Brewing Company, offers tours and a tasting room. There are also several popular beaches in Kihei to enjoy, including the Kamaole Beaches, Keawakapu Beach, and Waipuilani Park.

Whether you choose to stay at a resort, in a Wailea condo or a vacation home, you will appreciate the variety of activities and attractions nearby.

Wailea Real Estate For Sale

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Short Term Rental
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$2,950,000

Wailea Elua 2012

3600 Wailea Alanui Dr 2012, Wailea/Makena

1 Bed 2 Baths 1,031 SqFt Residential MLS® # 409117

Days on Market: 171

Coldwell Banker Island Prop(S) Cell: 808-425-3566

Listing Image for 3950 Kalai Waa St Y-202 1 of 44 Listing Image for 3950 Kalai Waa St Y-202 2 of 44 Listing Image for 3950 Kalai Waa St Y-202 3 of 44 Listing Image for 3950 Kalai Waa St Y-202 4 of 44 Listing Image for 3950 Kalai Waa St Y-202 5 of 44 Listing Image for 3950 Kalai Waa St Y-202 6 of 44 Listing Image for 3950 Kalai Waa St Y-202 7 of 44 Listing Image for 3950 Kalai Waa St Y-202 8 of 44 Listing Image for 3950 Kalai Waa St Y-202 9 of 44 Listing Image for 3950 Kalai Waa St Y-202 10 of 44 Listing Image for 3950 Kalai Waa St Y-202 11 of 44 Listing Image for 3950 Kalai Waa St Y-202 12 of 44 Listing Image for 3950 Kalai Waa St Y-202 13 of 44 Listing Image for 3950 Kalai Waa St Y-202 14 of 44 Listing Image for 3950 Kalai Waa St Y-202 15 of 44 Listing Image for 3950 Kalai Waa St Y-202 16 of 44 Listing Image for 3950 Kalai Waa St Y-202 17 of 44 Listing Image for 3950 Kalai Waa St Y-202 18 of 44 Listing Image for 3950 Kalai Waa St Y-202 19 of 44 Listing Image for 3950 Kalai Waa St Y-202 20 of 44 Listing Image for 3950 Kalai Waa St Y-202 21 of 44 Listing Image for 3950 Kalai Waa St Y-202 22 of 44 Listing Image for 3950 Kalai Waa St Y-202 23 of 44 Listing Image for 3950 Kalai Waa St Y-202 24 of 44 Listing Image for 3950 Kalai Waa St Y-202 25 of 44 Listing Image for 3950 Kalai Waa St Y-202 26 of 44 Listing Image for 3950 Kalai Waa St Y-202 27 of 44 Listing Image for 3950 Kalai Waa St Y-202 28 of 44 Listing Image for 3950 Kalai Waa St Y-202 29 of 44 Listing Image for 3950 Kalai Waa St Y-202 30 of 44 Listing Image for 3950 Kalai Waa St Y-202 31 of 44 Listing Image for 3950 Kalai Waa St Y-202 32 of 44 Listing Image for 3950 Kalai Waa St Y-202 33 of 44 Listing Image for 3950 Kalai Waa St Y-202 34 of 44 Listing Image for 3950 Kalai Waa St Y-202 35 of 44 Listing Image for 3950 Kalai Waa St Y-202 36 of 44 Listing Image for 3950 Kalai Waa St Y-202 37 of 44 Listing Image for 3950 Kalai Waa St Y-202 38 of 44 Listing Image for 3950 Kalai Waa St Y-202 39 of 44 Listing Image for 3950 Kalai Waa St Y-202 40 of 44 Listing Image for 3950 Kalai Waa St Y-202 41 of 44 Listing Image for 3950 Kalai Waa St Y-202 42 of 44 Listing Image for 3950 Kalai Waa St Y-202 43 of 44 Listing Image for 3950 Kalai Waa St Y-202 44 of 44

$1,189,000

Wailea Fairway Villas Y-202

3950 Kalai Waa St Y-202, Wailea/Makena

2 Beds 2 Baths 949 SqFt Residential MLS® # 409105

Days on Market: 173

Hawaii Life (W) Cell: 808-870-8668

Listing Image for 5417 Makena Rd 2 1 of 16 Listing Image for 5417 Makena Rd 2 2 of 16 Listing Image for 5417 Makena Rd 2 3 of 16 Listing Image for 5417 Makena Rd 2 4 of 16 Listing Image for 5417 Makena Rd 2 5 of 16 Listing Image for 5417 Makena Rd 2 6 of 16 Listing Image for 5417 Makena Rd 2 7 of 16 Listing Image for 5417 Makena Rd 2 8 of 16 Listing Image for 5417 Makena Rd 2 9 of 16 Listing Image for 5417 Makena Rd 2 10 of 16 Listing Image for 5417 Makena Rd 2 11 of 16 Listing Image for 5417 Makena Rd 2 12 of 16 Listing Image for 5417 Makena Rd 2 13 of 16 Listing Image for 5417 Makena Rd 2 14 of 16 Listing Image for 5417 Makena Rd 2 15 of 16 Listing Image for 5417 Makena Rd 2 16 of 16

$18,900,000

↓ $1,100,000

Wailea/Makena

5417 Makena Rd 2, Wailea/Makena

4 Beds 5 Baths 3,834 SqFt Residential MLS® # 409020

Days on Market: 185

Discovery Makena Realty LLC Cell: 808-870-8000

Listing Image for 63 Wailea Gateway Pl 5103 1 of 40 Listing Image for 63 Wailea Gateway Pl 5103 2 of 40 Listing Image for 63 Wailea Gateway Pl 5103 3 of 40 Listing Image for 63 Wailea Gateway Pl 5103 4 of 40 Listing Image for 63 Wailea Gateway Pl 5103 5 of 40 Listing Image for 63 Wailea Gateway Pl 5103 6 of 40 Listing Image for 63 Wailea Gateway Pl 5103 7 of 40 Listing Image for 63 Wailea Gateway Pl 5103 8 of 40 Listing Image for 63 Wailea Gateway Pl 5103 9 of 40 Listing Image for 63 Wailea Gateway Pl 5103 10 of 40 Listing Image for 63 Wailea Gateway Pl 5103 11 of 40 Listing Image for 63 Wailea Gateway Pl 5103 12 of 40 Listing Image for 63 Wailea Gateway Pl 5103 13 of 40 Listing Image for 63 Wailea Gateway Pl 5103 14 of 40 Listing Image for 63 Wailea Gateway Pl 5103 15 of 40 Listing Image for 63 Wailea Gateway Pl 5103 16 of 40 Listing Image for 63 Wailea Gateway Pl 5103 17 of 40 Listing Image for 63 Wailea Gateway Pl 5103 18 of 40 Listing Image for 63 Wailea Gateway Pl 5103 19 of 40 Listing Image for 63 Wailea Gateway Pl 5103 20 of 40 Listing Image for 63 Wailea Gateway Pl 5103 21 of 40 Listing Image for 63 Wailea Gateway Pl 5103 22 of 40 Listing Image for 63 Wailea Gateway Pl 5103 23 of 40 Listing Image for 63 Wailea Gateway Pl 5103 24 of 40 Listing Image for 63 Wailea Gateway Pl 5103 25 of 40 Listing Image for 63 Wailea Gateway Pl 5103 26 of 40 Listing Image for 63 Wailea Gateway Pl 5103 27 of 40 Listing Image for 63 Wailea Gateway Pl 5103 28 of 40 Listing Image for 63 Wailea Gateway Pl 5103 29 of 40 Listing Image for 63 Wailea Gateway Pl 5103 30 of 40 Listing Image for 63 Wailea Gateway Pl 5103 31 of 40 Listing Image for 63 Wailea Gateway Pl 5103 32 of 40 Listing Image for 63 Wailea Gateway Pl 5103 33 of 40 Listing Image for 63 Wailea Gateway Pl 5103 34 of 40 Listing Image for 63 Wailea Gateway Pl 5103 35 of 40 Listing Image for 63 Wailea Gateway Pl 5103 36 of 40 Listing Image for 63 Wailea Gateway Pl 5103 37 of 40 Listing Image for 63 Wailea Gateway Pl 5103 38 of 40 Listing Image for 63 Wailea Gateway Pl 5103 39 of 40 Listing Image for 63 Wailea Gateway Pl 5103 40 of 40

$2,100,000

↓ $150,000

Keala O Wailea 5103

63 Wailea Gateway Pl 5103, Wailea/Makena

2 Beds 2 Baths 1,248 SqFt Residential MLS® # 408944

Days on Market: 192

Coldwell Banker Island Prop(S) Cell: 808-298-7910

Buying Real Estate on Maui

Buying Real Estate on Maui

Read Evan's complete guide to buying a home or condo on Maui.

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In Escrow
Listing Image for 4584 Makena Rd 1 of 30 Listing Image for 4584 Makena Rd 2 of 30 Listing Image for 4584 Makena Rd 3 of 30 Listing Image for 4584 Makena Rd 4 of 30 Listing Image for 4584 Makena Rd 5 of 30 Listing Image for 4584 Makena Rd 6 of 30 Listing Image for 4584 Makena Rd 7 of 30 Listing Image for 4584 Makena Rd 8 of 30 Listing Image for 4584 Makena Rd 9 of 30 Listing Image for 4584 Makena Rd 10 of 30 Listing Image for 4584 Makena Rd 11 of 30 Listing Image for 4584 Makena Rd 12 of 30 Listing Image for 4584 Makena Rd 13 of 30 Listing Image for 4584 Makena Rd 14 of 30 Listing Image for 4584 Makena Rd 15 of 30 Listing Image for 4584 Makena Rd 16 of 30 Listing Image for 4584 Makena Rd 17 of 30 Listing Image for 4584 Makena Rd 18 of 30 Listing Image for 4584 Makena Rd 19 of 30 Listing Image for 4584 Makena Rd 20 of 30 Listing Image for 4584 Makena Rd 21 of 30 Listing Image for 4584 Makena Rd 22 of 30 Listing Image for 4584 Makena Rd 23 of 30 Listing Image for 4584 Makena Rd 24 of 30 Listing Image for 4584 Makena Rd 25 of 30 Listing Image for 4584 Makena Rd 26 of 30 Listing Image for 4584 Makena Rd 27 of 30 Listing Image for 4584 Makena Rd 28 of 30 Listing Image for 4584 Makena Rd 29 of 30 Listing Image for 4584 Makena Rd 30 of 30

$9,000,000

Wailea/Makena

4584 Makena Rd, Wailea/Makena

2 Beds 3.5 Baths 2,760 SqFt Residential MLS® # 408876

Days on Market: 199

Island Sotheby's International Realty(W) Cell: 808-283-7965

Short Term Rental
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$1,335,000

↓ $100,000

Wailea Ekolu 203

10 Wailea Ekolu Pl 203, Wailea/Makena

2 Beds 2 Baths 1,071 SqFt Residential MLS® # 408874

Days on Market: 199

Hawaii Life (W) Cell: 808-208-1385

View 6 More Listings

Kaanapali: World-Famous Beaches and Hawaiian Culture

Ka'anapali Maui

Kaanapali is located on Maui’s west coast, only a short drive north of Lahaina. Kaanapali is a planned resort community with a laid-back ambiance

Resort Experiences in Ka'anapali

In addition to the numerous rental condos and homes available in Kaanapali, several resorts are available.

If you choose to stay in Kaanapali, the Royal Lahaina Resort and Bungalows, the Sheraton Maui Resort and Spa and the Honua Kai are great options to consider.

Outdoor Activities

Kaanapali Beach is regarded as one of the top beaches on the island due to its soft sands that extend into the water. The beach spans three miles and boasts crystal-clear water and lifeguard coverage. Several resorts and the Whalers Village retail complex have frontage on the beach.

Whalers Village features a whaling museum, top-rated restaurants, shops, and entertainment. Each day, cliff divers perform at Black Rock on Kaanapali Beach.

This performance pays tribute to a famed Hawaiian king. Other activities near the beach are ziplining, sailing adventures, dinner cruises, and whale watching.

Final Thoughts

With incredible experiences and attractions to enjoy throughout the island, where you stay in Maui is an important consideration when planning your trip. Both Kaanapali and Wailea offer many resorts, condos, and homes to stay at for your upcoming trip.

Get In Touch With Evan!

Evan Harlow Maui

Evan Harlow ranks among the best real estate agents on Maui annually and is in the top 1% of Coldwell Banker agents worldwide in production. Evan has the expertise, experience, and work ethic to help you achieve your real estate buying and selling goals. We promise exceptional service and support from the beginning of the process through closing and beyond. See what Evan's clients are saying on Google.

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