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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Listing Image for 100 Poailani Pl 29 1 of 50 Listing Image for 100 Poailani Pl 29 2 of 50 Listing Image for 100 Poailani Pl 29 3 of 50 Listing Image for 100 Poailani Pl 29 4 of 50 Listing Image for 100 Poailani Pl 29 5 of 50 Listing Image for 100 Poailani Pl 29 6 of 50 Listing Image for 100 Poailani Pl 29 7 of 50 Listing Image for 100 Poailani Pl 29 8 of 50 Listing Image for 100 Poailani Pl 29 9 of 50 Listing Image for 100 Poailani Pl 29 10 of 50 Listing Image for 100 Poailani Pl 29 11 of 50 Listing Image for 100 Poailani Pl 29 12 of 50 Listing Image for 100 Poailani Pl 29 13 of 50 Listing Image for 100 Poailani Pl 29 14 of 50 Listing Image for 100 Poailani Pl 29 15 of 50 Listing Image for 100 Poailani Pl 29 16 of 50 Listing Image for 100 Poailani Pl 29 17 of 50 Listing Image for 100 Poailani Pl 29 18 of 50 Listing Image for 100 Poailani Pl 29 19 of 50 Listing Image for 100 Poailani Pl 29 20 of 50 Listing Image for 100 Poailani Pl 29 21 of 50 Listing Image for 100 Poailani Pl 29 22 of 50 Listing Image for 100 Poailani Pl 29 23 of 50 Listing Image for 100 Poailani Pl 29 24 of 50 Listing Image for 100 Poailani Pl 29 25 of 50 Listing Image for 100 Poailani Pl 29 26 of 50 Listing Image for 100 Poailani Pl 29 27 of 50 Listing Image for 100 Poailani Pl 29 28 of 50 Listing Image for 100 Poailani Pl 29 29 of 50 Listing Image for 100 Poailani Pl 29 30 of 50 Listing Image for 100 Poailani Pl 29 31 of 50 Listing Image for 100 Poailani Pl 29 32 of 50 Listing Image for 100 Poailani Pl 29 33 of 50 Listing Image for 100 Poailani Pl 29 34 of 50 Listing Image for 100 Poailani Pl 29 35 of 50 Listing Image for 100 Poailani Pl 29 36 of 50 Listing Image for 100 Poailani Pl 29 37 of 50 Listing Image for 100 Poailani Pl 29 38 of 50 Listing Image for 100 Poailani Pl 29 39 of 50 Listing Image for 100 Poailani Pl 29 40 of 50 Listing Image for 100 Poailani Pl 29 41 of 50 Listing Image for 100 Poailani Pl 29 42 of 50 Listing Image for 100 Poailani Pl 29 43 of 50 Listing Image for 100 Poailani Pl 29 44 of 50 Listing Image for 100 Poailani Pl 29 45 of 50 Listing Image for 100 Poailani Pl 29 46 of 50 Listing Image for 100 Poailani Pl 29 47 of 50 Listing Image for 100 Poailani Pl 29 48 of 50 Listing Image for 100 Poailani Pl 29 49 of 50 Listing Image for 100 Poailani Pl 29 50 of 50

$2,595,000

↓ $100,000

Kanani Wailea

100 Poailani Pl 29, Wailea/Makena

4 Beds 4 Baths 2,129 SqFt Residential MLS® # 409490

Days on Market: 136

McEntire Realty

Short Term Rental
Listing Image for 10 Wailea Ekolu Pl 1206 1 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 2 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 3 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 4 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 5 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 6 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 7 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 8 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 9 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 10 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 11 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 12 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 13 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 14 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 15 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 16 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 17 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 18 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 19 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 20 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 21 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 22 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 23 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 24 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 25 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 26 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 27 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 28 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 29 of 30 Listing Image for 10 Wailea Ekolu Pl 1206 30 of 30

$1,475,000

Wailea Ekolu 1206

10 Wailea Ekolu Pl 1206, Wailea/Makena

2 Beds 2 Baths 1,071 SqFt Residential MLS® # 409483

Days on Market: 135

Coldwell Banker Island Prop-Ku Cell: 808-250-6754

Listing Image for 100 Poailani Pl 29 1 of 50 Listing Image for 100 Poailani Pl 29 2 of 50 Listing Image for 100 Poailani Pl 29 3 of 50 Listing Image for 100 Poailani Pl 29 4 of 50 Listing Image for 100 Poailani Pl 29 5 of 50 Listing Image for 100 Poailani Pl 29 6 of 50 Listing Image for 100 Poailani Pl 29 7 of 50 Listing Image for 100 Poailani Pl 29 8 of 50 Listing Image for 100 Poailani Pl 29 9 of 50 Listing Image for 100 Poailani Pl 29 10 of 50 Listing Image for 100 Poailani Pl 29 11 of 50 Listing Image for 100 Poailani Pl 29 12 of 50 Listing Image for 100 Poailani Pl 29 13 of 50 Listing Image for 100 Poailani Pl 29 14 of 50 Listing Image for 100 Poailani Pl 29 15 of 50 Listing Image for 100 Poailani Pl 29 16 of 50 Listing Image for 100 Poailani Pl 29 17 of 50 Listing Image for 100 Poailani Pl 29 18 of 50 Listing Image for 100 Poailani Pl 29 19 of 50 Listing Image for 100 Poailani Pl 29 20 of 50 Listing Image for 100 Poailani Pl 29 21 of 50 Listing Image for 100 Poailani Pl 29 22 of 50 Listing Image for 100 Poailani Pl 29 23 of 50 Listing Image for 100 Poailani Pl 29 24 of 50 Listing Image for 100 Poailani Pl 29 25 of 50 Listing Image for 100 Poailani Pl 29 26 of 50 Listing Image for 100 Poailani Pl 29 27 of 50 Listing Image for 100 Poailani Pl 29 28 of 50 Listing Image for 100 Poailani Pl 29 29 of 50 Listing Image for 100 Poailani Pl 29 30 of 50 Listing Image for 100 Poailani Pl 29 31 of 50 Listing Image for 100 Poailani Pl 29 32 of 50 Listing Image for 100 Poailani Pl 29 33 of 50 Listing Image for 100 Poailani Pl 29 34 of 50 Listing Image for 100 Poailani Pl 29 35 of 50 Listing Image for 100 Poailani Pl 29 36 of 50 Listing Image for 100 Poailani Pl 29 37 of 50 Listing Image for 100 Poailani Pl 29 38 of 50 Listing Image for 100 Poailani Pl 29 39 of 50 Listing Image for 100 Poailani Pl 29 40 of 50 Listing Image for 100 Poailani Pl 29 41 of 50 Listing Image for 100 Poailani Pl 29 42 of 50 Listing Image for 100 Poailani Pl 29 43 of 50 Listing Image for 100 Poailani Pl 29 44 of 50 Listing Image for 100 Poailani Pl 29 45 of 50 Listing Image for 100 Poailani Pl 29 46 of 50 Listing Image for 100 Poailani Pl 29 47 of 50 Listing Image for 100 Poailani Pl 29 48 of 50 Listing Image for 100 Poailani Pl 29 49 of 50 Listing Image for 100 Poailani Pl 29 50 of 50

$2,595,000

↓ $100,000

Kanani Wailea 29

100 Poailani Pl 29, Wailea/Makena

4 Beds 4 Baths 2,129 SqFt Residential MLS® # 409467

Days on Market: 136

McEntire Realty

Listing Image for 3950 Kalai Waa St U202 1 of 26 Listing Image for 3950 Kalai Waa St U202 2 of 26 Listing Image for 3950 Kalai Waa St U202 3 of 26 Listing Image for 3950 Kalai Waa St U202 4 of 26 Listing Image for 3950 Kalai Waa St U202 5 of 26 Listing Image for 3950 Kalai Waa St U202 6 of 26 Listing Image for 3950 Kalai Waa St U202 7 of 26 Listing Image for 3950 Kalai Waa St U202 8 of 26 Listing Image for 3950 Kalai Waa St U202 9 of 26 Listing Image for 3950 Kalai Waa St U202 10 of 26 Listing Image for 3950 Kalai Waa St U202 11 of 26 Listing Image for 3950 Kalai Waa St U202 12 of 26 Listing Image for 3950 Kalai Waa St U202 13 of 26 Listing Image for 3950 Kalai Waa St U202 14 of 26 Listing Image for 3950 Kalai Waa St U202 15 of 26 Listing Image for 3950 Kalai Waa St U202 16 of 26 Listing Image for 3950 Kalai Waa St U202 17 of 26 Listing Image for 3950 Kalai Waa St U202 18 of 26 Listing Image for 3950 Kalai Waa St U202 19 of 26 Listing Image for 3950 Kalai Waa St U202 20 of 26 Listing Image for 3950 Kalai Waa St U202 21 of 26 Listing Image for 3950 Kalai Waa St U202 22 of 26 Listing Image for 3950 Kalai Waa St U202 23 of 26 Listing Image for 3950 Kalai Waa St U202 24 of 26 Listing Image for 3950 Kalai Waa St U202 25 of 26 Listing Image for 3950 Kalai Waa St U202 26 of 26

$999,500

Wailea Fairway Villas U202

3950 Kalai Waa St U202, Wailea/Makena

2 Beds 2 Baths 949 SqFt Residential MLS® # 409449

Days on Market: 137

Berkshire Hathaway Maui Prop-W

Listing Image for 4000 Wailea Alanui Dr 802 & 804 1 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 2 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 3 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 4 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 5 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 6 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 7 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 8 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 9 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 10 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 11 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 12 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 13 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 14 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 15 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 16 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 17 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 18 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 19 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 20 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 21 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 22 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 23 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 24 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 25 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 26 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 27 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 28 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 29 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 30 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 31 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 32 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 33 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 34 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 35 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 36 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 37 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 38 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 39 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 40 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 41 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 42 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 43 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 44 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 45 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 46 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 47 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 48 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 49 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 50 of 50

$8,740,000

Wailea Point 802 & 804

4000 Wailea Alanui Dr 802 & 804, Wailea/Makena

5 Beds 6 Baths 4,913 SqFt Residential MLS® # 409447

Days on Market: 137

Wailea Point Realty, Inc. realty@waileapoint.com

Listing Image for 17 Maluaka Pl Unit 5 1 of 19 Listing Image for 17 Maluaka Pl Unit 5 2 of 19 Listing Image for 17 Maluaka Pl Unit 5 3 of 19 Listing Image for 17 Maluaka Pl Unit 5 4 of 19 Listing Image for 17 Maluaka Pl Unit 5 5 of 19 Listing Image for 17 Maluaka Pl Unit 5 6 of 19 Listing Image for 17 Maluaka Pl Unit 5 7 of 19 Listing Image for 17 Maluaka Pl Unit 5 8 of 19 Listing Image for 17 Maluaka Pl Unit 5 9 of 19 Listing Image for 17 Maluaka Pl Unit 5 10 of 19 Listing Image for 17 Maluaka Pl Unit 5 11 of 19 Listing Image for 17 Maluaka Pl Unit 5 12 of 19 Listing Image for 17 Maluaka Pl Unit 5 13 of 19 Listing Image for 17 Maluaka Pl Unit 5 14 of 19 Listing Image for 17 Maluaka Pl Unit 5 15 of 19 Listing Image for 17 Maluaka Pl Unit 5 16 of 19 Listing Image for 17 Maluaka Pl Unit 5 17 of 19 Listing Image for 17 Maluaka Pl Unit 5 18 of 19 Listing Image for 17 Maluaka Pl Unit 5 19 of 19

$9,950,000

Wailea/Makena

17 Maluaka Pl Unit 5, Wailea/Makena

0 Beds 0 Baths 0 SqFt Land MLS® # 409403

Days on Market: 142

Island Sotheby's Int'l Rlty(W) Cell: 808-283-7965

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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