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 3300 Wailea Alanui Dr 40e 1 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 2 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 3 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 4 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 5 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 6 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 7 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 8 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 9 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 10 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 11 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 12 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 13 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 14 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 15 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 16 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 17 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 18 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 19 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 20 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 21 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 22 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 23 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 24 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 25 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 26 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 27 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 28 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 29 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 30 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 31 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 32 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 33 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 34 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 35 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 36 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 37 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 38 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 39 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 40 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 41 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 42 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 43 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 44 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 45 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 46 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 47 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 48 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 49 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 50 of 50

$1,399,000

Wailea Ekahi 40E

3300 Wailea Alanui Dr 40e, Wailea/Makena

1 Bed 2 Baths 952 SqFt Residential MLS® # 410343

Days on Market: 52

Romvari Realty Ltd

Listing Image for 3100 Wailea Alanui Dr 17 1 of 49 Listing Image for 3100 Wailea Alanui Dr 17 2 of 49 Listing Image for 3100 Wailea Alanui Dr 17 3 of 49 Listing Image for 3100 Wailea Alanui Dr 17 4 of 49 Listing Image for 3100 Wailea Alanui Dr 17 5 of 49 Listing Image for 3100 Wailea Alanui Dr 17 6 of 49 Listing Image for 3100 Wailea Alanui Dr 17 7 of 49 Listing Image for 3100 Wailea Alanui Dr 17 8 of 49 Listing Image for 3100 Wailea Alanui Dr 17 9 of 49 Listing Image for 3100 Wailea Alanui Dr 17 10 of 49 Listing Image for 3100 Wailea Alanui Dr 17 11 of 49 Listing Image for 3100 Wailea Alanui Dr 17 12 of 49 Listing Image for 3100 Wailea Alanui Dr 17 13 of 49 Listing Image for 3100 Wailea Alanui Dr 17 14 of 49 Listing Image for 3100 Wailea Alanui Dr 17 15 of 49 Listing Image for 3100 Wailea Alanui Dr 17 16 of 49 Listing Image for 3100 Wailea Alanui Dr 17 17 of 49 Listing Image for 3100 Wailea Alanui Dr 17 18 of 49 Listing Image for 3100 Wailea Alanui Dr 17 19 of 49 Listing Image for 3100 Wailea Alanui Dr 17 20 of 49 Listing Image for 3100 Wailea Alanui Dr 17 21 of 49 Listing Image for 3100 Wailea Alanui Dr 17 22 of 49 Listing Image for 3100 Wailea Alanui Dr 17 23 of 49 Listing Image for 3100 Wailea Alanui Dr 17 24 of 49 Listing Image for 3100 Wailea Alanui Dr 17 25 of 49 Listing Image for 3100 Wailea Alanui Dr 17 26 of 49 Listing Image for 3100 Wailea Alanui Dr 17 27 of 49 Listing Image for 3100 Wailea Alanui Dr 17 28 of 49 Listing Image for 3100 Wailea Alanui Dr 17 29 of 49 Listing Image for 3100 Wailea Alanui Dr 17 30 of 49 Listing Image for 3100 Wailea Alanui Dr 17 31 of 49 Listing Image for 3100 Wailea Alanui Dr 17 32 of 49 Listing Image for 3100 Wailea Alanui Dr 17 33 of 49 Listing Image for 3100 Wailea Alanui Dr 17 34 of 49 Listing Image for 3100 Wailea Alanui Dr 17 35 of 49 Listing Image for 3100 Wailea Alanui Dr 17 36 of 49 Listing Image for 3100 Wailea Alanui Dr 17 37 of 49 Listing Image for 3100 Wailea Alanui Dr 17 38 of 49 Listing Image for 3100 Wailea Alanui Dr 17 39 of 49 Listing Image for 3100 Wailea Alanui Dr 17 40 of 49 Listing Image for 3100 Wailea Alanui Dr 17 41 of 49 Listing Image for 3100 Wailea Alanui Dr 17 42 of 49 Listing Image for 3100 Wailea Alanui Dr 17 43 of 49 Listing Image for 3100 Wailea Alanui Dr 17 44 of 49 Listing Image for 3100 Wailea Alanui Dr 17 45 of 49 Listing Image for 3100 Wailea Alanui Dr 17 46 of 49 Listing Image for 3100 Wailea Alanui Dr 17 47 of 49 Listing Image for 3100 Wailea Alanui Dr 17 48 of 49 Listing Image for 3100 Wailea Alanui Dr 17 49 of 49

$4,795,000

Papali Wailea 17

3100 Wailea Alanui Dr 17, Wailea/Makena

3 Beds 3.5 Baths 2,386 SqFt Residential MLS® # 410334

Days on Market: 53

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

Listing Image for 5412 Makena Alanui Rd 102/kv-3b 1 of 2 Listing Image for 5412 Makena Alanui Rd 102/kv-3b 2 of 2

$12,500,000

Makena Beach Club & Residences 102/KV-3B

5412 Makena Alanui Rd 102/kv-3b, Wailea/Makena

4 Beds 4.5 Baths 3,834 SqFt Residential MLS® # 407694

Days on Market: 307

Discovery Makena Realty LLC

Listing Image for 5050 Makena Rd 1 of 19 Listing Image for 5050 Makena Rd 2 of 19 Listing Image for 5050 Makena Rd 3 of 19 Listing Image for 5050 Makena Rd 4 of 19 Listing Image for 5050 Makena Rd 5 of 19 Listing Image for 5050 Makena Rd 6 of 19 Listing Image for 5050 Makena Rd 7 of 19 Listing Image for 5050 Makena Rd 8 of 19 Listing Image for 5050 Makena Rd 9 of 19 Listing Image for 5050 Makena Rd 10 of 19 Listing Image for 5050 Makena Rd 11 of 19 Listing Image for 5050 Makena Rd 12 of 19 Listing Image for 5050 Makena Rd 13 of 19 Listing Image for 5050 Makena Rd 14 of 19 Listing Image for 5050 Makena Rd 15 of 19 Listing Image for 5050 Makena Rd 16 of 19 Listing Image for 5050 Makena Rd 17 of 19 Listing Image for 5050 Makena Rd 18 of 19 Listing Image for 5050 Makena Rd 19 of 19

$29,900,000

Wailea/Makena

5050 Makena Rd, Wailea/Makena

5 Beds 5.5 Baths 9,176 SqFt Residential MLS® # 407766

Days on Market: 303

Discovery Makena Realty LLC Cell: 808-870-8000

Listing Image for 208 Holomoana Way 14b 1 of 50 Listing Image for 208 Holomoana Way 14b 2 of 50 Listing Image for 208 Holomoana Way 14b 3 of 50 Listing Image for 208 Holomoana Way 14b 4 of 50 Listing Image for 208 Holomoana Way 14b 5 of 50 Listing Image for 208 Holomoana Way 14b 6 of 50 Listing Image for 208 Holomoana Way 14b 7 of 50 Listing Image for 208 Holomoana Way 14b 8 of 50 Listing Image for 208 Holomoana Way 14b 9 of 50 Listing Image for 208 Holomoana Way 14b 10 of 50 Listing Image for 208 Holomoana Way 14b 11 of 50 Listing Image for 208 Holomoana Way 14b 12 of 50 Listing Image for 208 Holomoana Way 14b 13 of 50 Listing Image for 208 Holomoana Way 14b 14 of 50 Listing Image for 208 Holomoana Way 14b 15 of 50 Listing Image for 208 Holomoana Way 14b 16 of 50 Listing Image for 208 Holomoana Way 14b 17 of 50 Listing Image for 208 Holomoana Way 14b 18 of 50 Listing Image for 208 Holomoana Way 14b 19 of 50 Listing Image for 208 Holomoana Way 14b 20 of 50 Listing Image for 208 Holomoana Way 14b 21 of 50 Listing Image for 208 Holomoana Way 14b 22 of 50 Listing Image for 208 Holomoana Way 14b 23 of 50 Listing Image for 208 Holomoana Way 14b 24 of 50 Listing Image for 208 Holomoana Way 14b 25 of 50 Listing Image for 208 Holomoana Way 14b 26 of 50 Listing Image for 208 Holomoana Way 14b 27 of 50 Listing Image for 208 Holomoana Way 14b 28 of 50 Listing Image for 208 Holomoana Way 14b 29 of 50 Listing Image for 208 Holomoana Way 14b 30 of 50 Listing Image for 208 Holomoana Way 14b 31 of 50 Listing Image for 208 Holomoana Way 14b 32 of 50 Listing Image for 208 Holomoana Way 14b 33 of 50 Listing Image for 208 Holomoana Way 14b 34 of 50 Listing Image for 208 Holomoana Way 14b 35 of 50 Listing Image for 208 Holomoana Way 14b 36 of 50 Listing Image for 208 Holomoana Way 14b 37 of 50 Listing Image for 208 Holomoana Way 14b 38 of 50 Listing Image for 208 Holomoana Way 14b 39 of 50 Listing Image for 208 Holomoana Way 14b 40 of 50 Listing Image for 208 Holomoana Way 14b 41 of 50 Listing Image for 208 Holomoana Way 14b 42 of 50 Listing Image for 208 Holomoana Way 14b 43 of 50 Listing Image for 208 Holomoana Way 14b 44 of 50 Listing Image for 208 Holomoana Way 14b 45 of 50 Listing Image for 208 Holomoana Way 14b 46 of 50 Listing Image for 208 Holomoana Way 14b 47 of 50 Listing Image for 208 Holomoana Way 14b 48 of 50 Listing Image for 208 Holomoana Way 14b 49 of 50 Listing Image for 208 Holomoana Way 14b 50 of 50

$3,695,000

Makalii at Wailea 14B

208 Holomoana Way 14b, Wailea/Makena

3 Beds 3 Baths 1,802 SqFt Residential MLS® # 410261

Days on Market: 60

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

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

$1,079,000

Wailea Fairway Villas S-202

3950 Kalai Waa St S-202, Wailea/Makena

2 Beds 2 Baths 949 SqFt Residential MLS® # 410253

Days on Market: 61

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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