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 139 Waaula Way 1 of 50 Listing Image for 139 Waaula Way 2 of 50 Listing Image for 139 Waaula Way 3 of 50 Listing Image for 139 Waaula Way 4 of 50 Listing Image for 139 Waaula Way 5 of 50 Listing Image for 139 Waaula Way 6 of 50 Listing Image for 139 Waaula Way 7 of 50 Listing Image for 139 Waaula Way 8 of 50 Listing Image for 139 Waaula Way 9 of 50 Listing Image for 139 Waaula Way 10 of 50 Listing Image for 139 Waaula Way 11 of 50 Listing Image for 139 Waaula Way 12 of 50 Listing Image for 139 Waaula Way 13 of 50 Listing Image for 139 Waaula Way 14 of 50 Listing Image for 139 Waaula Way 15 of 50 Listing Image for 139 Waaula Way 16 of 50 Listing Image for 139 Waaula Way 17 of 50 Listing Image for 139 Waaula Way 18 of 50 Listing Image for 139 Waaula Way 19 of 50 Listing Image for 139 Waaula Way 20 of 50 Listing Image for 139 Waaula Way 21 of 50 Listing Image for 139 Waaula Way 22 of 50 Listing Image for 139 Waaula Way 23 of 50 Listing Image for 139 Waaula Way 24 of 50 Listing Image for 139 Waaula Way 25 of 50 Listing Image for 139 Waaula Way 26 of 50 Listing Image for 139 Waaula Way 27 of 50 Listing Image for 139 Waaula Way 28 of 50 Listing Image for 139 Waaula Way 29 of 50 Listing Image for 139 Waaula Way 30 of 50 Listing Image for 139 Waaula Way 31 of 50 Listing Image for 139 Waaula Way 32 of 50 Listing Image for 139 Waaula Way 33 of 50 Listing Image for 139 Waaula Way 34 of 50 Listing Image for 139 Waaula Way 35 of 50 Listing Image for 139 Waaula Way 36 of 50 Listing Image for 139 Waaula Way 37 of 50 Listing Image for 139 Waaula Way 38 of 50 Listing Image for 139 Waaula Way 39 of 50 Listing Image for 139 Waaula Way 40 of 50 Listing Image for 139 Waaula Way 41 of 50 Listing Image for 139 Waaula Way 42 of 50 Listing Image for 139 Waaula Way 43 of 50 Listing Image for 139 Waaula Way 44 of 50 Listing Image for 139 Waaula Way 45 of 50 Listing Image for 139 Waaula Way 46 of 50 Listing Image for 139 Waaula Way 47 of 50 Listing Image for 139 Waaula Way 48 of 50 Listing Image for 139 Waaula Way 49 of 50 Listing Image for 139 Waaula Way 50 of 50

$2,499,000

Wailea Kai

139 Waaula Way, Wailea/Makena

3 Beds 2.5 Baths 2,788 SqFt Residential MLS® # 410251

Days on Market: 61

Coldwell Banker Island Prop-Ku Cell: 808-757-6161

Listing Image for 3919 Waakaula Pl 1 of 35 Listing Image for 3919 Waakaula Pl 2 of 35 Listing Image for 3919 Waakaula Pl 3 of 35 Listing Image for 3919 Waakaula Pl 4 of 35 Listing Image for 3919 Waakaula Pl 5 of 35 Listing Image for 3919 Waakaula Pl 6 of 35 Listing Image for 3919 Waakaula Pl 7 of 35 Listing Image for 3919 Waakaula Pl 8 of 35 Listing Image for 3919 Waakaula Pl 9 of 35 Listing Image for 3919 Waakaula Pl 10 of 35 Listing Image for 3919 Waakaula Pl 11 of 35 Listing Image for 3919 Waakaula Pl 12 of 35 Listing Image for 3919 Waakaula Pl 13 of 35 Listing Image for 3919 Waakaula Pl 14 of 35 Listing Image for 3919 Waakaula Pl 15 of 35 Listing Image for 3919 Waakaula Pl 16 of 35 Listing Image for 3919 Waakaula Pl 17 of 35 Listing Image for 3919 Waakaula Pl 18 of 35 Listing Image for 3919 Waakaula Pl 19 of 35 Listing Image for 3919 Waakaula Pl 20 of 35 Listing Image for 3919 Waakaula Pl 21 of 35 Listing Image for 3919 Waakaula Pl 22 of 35 Listing Image for 3919 Waakaula Pl 23 of 35 Listing Image for 3919 Waakaula Pl 24 of 35 Listing Image for 3919 Waakaula Pl 25 of 35 Listing Image for 3919 Waakaula Pl 26 of 35 Listing Image for 3919 Waakaula Pl 27 of 35 Listing Image for 3919 Waakaula Pl 28 of 35 Listing Image for 3919 Waakaula Pl 29 of 35 Listing Image for 3919 Waakaula Pl 30 of 35 Listing Image for 3919 Waakaula Pl 31 of 35 Listing Image for 3919 Waakaula Pl 32 of 35 Listing Image for 3919 Waakaula Pl 33 of 35 Listing Image for 3919 Waakaula Pl 34 of 35 Listing Image for 3919 Waakaula Pl 35 of 35

$3,750,000

Wailea Golf Estates

3919 Waakaula Pl, Wailea/Makena

3 Beds 3 Baths 3,839 SqFt Residential MLS® # 410226

Days on Market: 64

Century 21 Island Homes

Short Term Rental
Listing Image for 10 Wailea Ekolu Pl 1706 1 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 2 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 3 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 4 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 5 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 6 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 7 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 8 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 9 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 10 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 11 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 12 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 13 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 14 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 15 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 16 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 17 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 18 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 19 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 20 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 21 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 22 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 23 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 24 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 25 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 26 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 27 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 28 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 29 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 30 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 31 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 32 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 33 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 34 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 35 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 36 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 37 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 38 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 39 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 40 of 40

$1,575,000

Wailea Ekolu 1706

10 Wailea Ekolu Pl 1706, Wailea/Makena

2 Beds 2 Baths 1,071 SqFt Residential MLS® # 410202

Days on Market: 66

Hawaii Life (W) Cell: 808-283-6791

Listing Image for 3200 S Wailea Alanui Dr 1 of 11 Listing Image for 3200 S Wailea Alanui Dr 2 of 11 Listing Image for 3200 S Wailea Alanui Dr 3 of 11 Listing Image for 3200 S Wailea Alanui Dr 4 of 11 Listing Image for 3200 S Wailea Alanui Dr 5 of 11 Listing Image for 3200 S Wailea Alanui Dr 6 of 11 Listing Image for 3200 S Wailea Alanui Dr 7 of 11 Listing Image for 3200 S Wailea Alanui Dr 8 of 11 Listing Image for 3200 S Wailea Alanui Dr 9 of 11 Listing Image for 3200 S Wailea Alanui Dr 10 of 11 Listing Image for 3200 S Wailea Alanui Dr 11 of 11

$4,500

↓ $400

Palms At Wailea

3200 S Wailea Alanui Dr, Wailea/Makena

2 Beds 2 Baths 1,194 SqFt Residential Lease MLS® # 410196

Days on Market: 67

eXp Realty Cell: 808-280-1333

Buying Real Estate on Maui

Buying Real Estate on Maui

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

Read the Guide
Listing Image for 4000 Wailea Alanui Dr 101 1 of 22 Listing Image for 4000 Wailea Alanui Dr 101 2 of 22 Listing Image for 4000 Wailea Alanui Dr 101 3 of 22 Listing Image for 4000 Wailea Alanui Dr 101 4 of 22 Listing Image for 4000 Wailea Alanui Dr 101 5 of 22 Listing Image for 4000 Wailea Alanui Dr 101 6 of 22 Listing Image for 4000 Wailea Alanui Dr 101 7 of 22 Listing Image for 4000 Wailea Alanui Dr 101 8 of 22 Listing Image for 4000 Wailea Alanui Dr 101 9 of 22 Listing Image for 4000 Wailea Alanui Dr 101 10 of 22 Listing Image for 4000 Wailea Alanui Dr 101 11 of 22 Listing Image for 4000 Wailea Alanui Dr 101 12 of 22 Listing Image for 4000 Wailea Alanui Dr 101 13 of 22 Listing Image for 4000 Wailea Alanui Dr 101 14 of 22 Listing Image for 4000 Wailea Alanui Dr 101 15 of 22 Listing Image for 4000 Wailea Alanui Dr 101 16 of 22 Listing Image for 4000 Wailea Alanui Dr 101 17 of 22 Listing Image for 4000 Wailea Alanui Dr 101 18 of 22 Listing Image for 4000 Wailea Alanui Dr 101 19 of 22 Listing Image for 4000 Wailea Alanui Dr 101 20 of 22 Listing Image for 4000 Wailea Alanui Dr 101 21 of 22 Listing Image for 4000 Wailea Alanui Dr 101 22 of 22

$13,900,000

Wailea Point 101

4000 Wailea Alanui Dr 101, Wailea/Makena

4 Beds 4 Baths 3,820 SqFt Residential MLS® # 410182

Days on Market: 68

Engel & Volkers Maui

Listing Image for 30 Kai Malu Dr 201 1 of 50 Listing Image for 30 Kai Malu Dr 201 2 of 50 Listing Image for 30 Kai Malu Dr 201 3 of 50 Listing Image for 30 Kai Malu Dr 201 4 of 50 Listing Image for 30 Kai Malu Dr 201 5 of 50 Listing Image for 30 Kai Malu Dr 201 6 of 50 Listing Image for 30 Kai Malu Dr 201 7 of 50 Listing Image for 30 Kai Malu Dr 201 8 of 50 Listing Image for 30 Kai Malu Dr 201 9 of 50 Listing Image for 30 Kai Malu Dr 201 10 of 50 Listing Image for 30 Kai Malu Dr 201 11 of 50 Listing Image for 30 Kai Malu Dr 201 12 of 50 Listing Image for 30 Kai Malu Dr 201 13 of 50 Listing Image for 30 Kai Malu Dr 201 14 of 50 Listing Image for 30 Kai Malu Dr 201 15 of 50 Listing Image for 30 Kai Malu Dr 201 16 of 50 Listing Image for 30 Kai Malu Dr 201 17 of 50 Listing Image for 30 Kai Malu Dr 201 18 of 50 Listing Image for 30 Kai Malu Dr 201 19 of 50 Listing Image for 30 Kai Malu Dr 201 20 of 50 Listing Image for 30 Kai Malu Dr 201 21 of 50 Listing Image for 30 Kai Malu Dr 201 22 of 50 Listing Image for 30 Kai Malu Dr 201 23 of 50 Listing Image for 30 Kai Malu Dr 201 24 of 50 Listing Image for 30 Kai Malu Dr 201 25 of 50 Listing Image for 30 Kai Malu Dr 201 26 of 50 Listing Image for 30 Kai Malu Dr 201 27 of 50 Listing Image for 30 Kai Malu Dr 201 28 of 50 Listing Image for 30 Kai Malu Dr 201 29 of 50 Listing Image for 30 Kai Malu Dr 201 30 of 50 Listing Image for 30 Kai Malu Dr 201 31 of 50 Listing Image for 30 Kai Malu Dr 201 32 of 50 Listing Image for 30 Kai Malu Dr 201 33 of 50 Listing Image for 30 Kai Malu Dr 201 34 of 50 Listing Image for 30 Kai Malu Dr 201 35 of 50 Listing Image for 30 Kai Malu Dr 201 36 of 50 Listing Image for 30 Kai Malu Dr 201 37 of 50 Listing Image for 30 Kai Malu Dr 201 38 of 50 Listing Image for 30 Kai Malu Dr 201 39 of 50 Listing Image for 30 Kai Malu Dr 201 40 of 50 Listing Image for 30 Kai Malu Dr 201 41 of 50 Listing Image for 30 Kai Malu Dr 201 42 of 50 Listing Image for 30 Kai Malu Dr 201 43 of 50 Listing Image for 30 Kai Malu Dr 201 44 of 50 Listing Image for 30 Kai Malu Dr 201 45 of 50 Listing Image for 30 Kai Malu Dr 201 46 of 50 Listing Image for 30 Kai Malu Dr 201 47 of 50 Listing Image for 30 Kai Malu Dr 201 48 of 50 Listing Image for 30 Kai Malu Dr 201 49 of 50 Listing Image for 30 Kai Malu Dr 201 50 of 50

$3,895,000

La'i Loa 201

30 Kai Malu Dr 201, Wailea/Makena

3 Beds 3 Baths 1,742 SqFt Residential MLS® # 410170

Days on Market: 68

Coldwell Banker Island Prop(S) Cell: 808-870-4899

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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