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 59 Wailea Gateway Pl 4-201 1 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 2 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 3 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 4 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 5 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 6 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 7 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 8 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 9 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 10 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 11 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 12 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 13 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 14 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 15 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 16 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 17 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 18 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 19 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 20 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 21 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 22 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 23 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 24 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 25 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 26 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 27 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 28 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 29 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 30 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 31 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 32 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 33 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 34 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 35 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 36 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 37 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 38 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 39 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 40 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 41 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 42 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 43 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 44 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 45 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 46 of 47 Listing Image for 59 Wailea Gateway Pl 4-201 47 of 47

$2,680,000

Keala O Wailea 4-201

59 Wailea Gateway Pl 4-201, Wailea/Makena

3 Beds 2 Baths 1,386 SqFt Residential MLS® # 410656

Days on Market: 15

Hawaii Life (W) Cell: 808-357-5000

In Escrow
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$2,850,000

Wailea Fairway Estates

85 Hale Alii Pl, Wailea/Makena

4 Beds 4 Baths 3,204 SqFt Residential MLS® # 410641

Days on Market: 17

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

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$2,600,000

WAILEA KIALOA

221 E Ikea Kai Pl, Wailea/Makena

4 Beds 4 Baths 2,921 SqFt Residential MLS® # 410606

Days on Market: 18

eXp Realty Cell: 808-280-1333

Short Term Rental
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$3,850,000

Hoolei T-1

24 Hoolei Cir T-1, Wailea/Makena

3 Beds 3.5 Baths 3,076 SqFt Residential MLS® # 410561

Days on Market: 24

Keller Williams Realty Maui-Ka Cell: 808-385-0882

Listing Image for 3376 E Lani Ikena Way Lot 209 1 of 8 Listing Image for 3376 E Lani Ikena Way Lot 209 2 of 8 Listing Image for 3376 E Lani Ikena Way Lot 209 3 of 8 Listing Image for 3376 E Lani Ikena Way Lot 209 4 of 8 Listing Image for 3376 E Lani Ikena Way Lot 209 5 of 8 Listing Image for 3376 E Lani Ikena Way Lot 209 6 of 8 Listing Image for 3376 E Lani Ikena Way Lot 209 7 of 8 Listing Image for 3376 E Lani Ikena Way Lot 209 8 of 8

$975,000

Wailea/Makena

3376 E Lani Ikena Way Lot 209, Wailea/Makena

0 Beds 0 Baths 0 SqFt Land MLS® # 410535

Days on Market: 29

Engel & Volkers Maui

Listing Image for 3111 Waiea Pl 1 of 41 Listing Image for 3111 Waiea Pl 2 of 41 Listing Image for 3111 Waiea Pl 3 of 41 Listing Image for 3111 Waiea Pl 4 of 41 Listing Image for 3111 Waiea Pl 5 of 41 Listing Image for 3111 Waiea Pl 6 of 41 Listing Image for 3111 Waiea Pl 7 of 41 Listing Image for 3111 Waiea Pl 8 of 41 Listing Image for 3111 Waiea Pl 9 of 41 Listing Image for 3111 Waiea Pl 10 of 41 Listing Image for 3111 Waiea Pl 11 of 41 Listing Image for 3111 Waiea Pl 12 of 41 Listing Image for 3111 Waiea Pl 13 of 41 Listing Image for 3111 Waiea Pl 14 of 41 Listing Image for 3111 Waiea Pl 15 of 41 Listing Image for 3111 Waiea Pl 16 of 41 Listing Image for 3111 Waiea Pl 17 of 41 Listing Image for 3111 Waiea Pl 18 of 41 Listing Image for 3111 Waiea Pl 19 of 41 Listing Image for 3111 Waiea Pl 20 of 41 Listing Image for 3111 Waiea Pl 21 of 41 Listing Image for 3111 Waiea Pl 22 of 41 Listing Image for 3111 Waiea Pl 23 of 41 Listing Image for 3111 Waiea Pl 24 of 41 Listing Image for 3111 Waiea Pl 25 of 41 Listing Image for 3111 Waiea Pl 26 of 41 Listing Image for 3111 Waiea Pl 27 of 41 Listing Image for 3111 Waiea Pl 28 of 41 Listing Image for 3111 Waiea Pl 29 of 41 Listing Image for 3111 Waiea Pl 30 of 41 Listing Image for 3111 Waiea Pl 31 of 41 Listing Image for 3111 Waiea Pl 32 of 41 Listing Image for 3111 Waiea Pl 33 of 41 Listing Image for 3111 Waiea Pl 34 of 41 Listing Image for 3111 Waiea Pl 35 of 41 Listing Image for 3111 Waiea Pl 36 of 41 Listing Image for 3111 Waiea Pl 37 of 41 Listing Image for 3111 Waiea Pl 38 of 41 Listing Image for 3111 Waiea Pl 39 of 41 Listing Image for 3111 Waiea Pl 40 of 41 Listing Image for 3111 Waiea Pl 41 of 41

$2,500,000

Wailea Kai

3111 Waiea Pl, Wailea/Makena

3 Beds 3 Baths 1,797 SqFt Residential MLS® # 410525

Days on Market: 29

Maui Luxury Real Estate LLC

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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.

Kaanapali Real Estate For Sale

New Short Term Rental
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$574,000

Kaanapali Shores 615

3445 Lower Honoapiilani Rd 615, Kaanapali

2 Beds 2 Baths 1,004 SqFt Residential MLS® # 410733

Days on Market: 7

Keller Williams Realty Maui-L Cell: 808-870-2525

New Short Term Rental
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$995,000

Whaler 1215

2481 Kaanapali Pkwy 1215, Kaanapali

0 Beds 1 Bath 523 SqFt Residential MLS® # 410730

Days on Market: 7

Keller Williams Realty Maui-L Cell: 808-870-2525

Listing Image for 2481 Kaanapali Pkwy 216 P 1 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 2 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 3 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 4 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 5 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 6 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 7 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 8 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 9 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 10 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 11 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 12 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 13 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 14 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 15 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 16 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 17 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 18 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 19 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 20 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 21 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 22 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 23 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 24 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 25 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 26 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 27 of 28 Listing Image for 2481 Kaanapali Pkwy 216 P 28 of 28

$27,500

Whaler 216 P

2481 Kaanapali Pkwy 216 P, Kaanapali

0 Beds 1 Bath 542 SqFt Residential Income MLS® # 410704

Days on Market: 10

Keller Williams Realty Maui-L Cell: 808-870-2525

Short Term Rental
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$2,400,000

Honua Kai - Konea NR919

130 Kai Malina Pkwy Nr919, Kaanapali

2 Beds 2 Baths 1,280 SqFt Residential MLS® # 410703

Days on Market: 10

Coldwell Banker Island Prop-KP Cell: 808-446-5841

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Nr1026 1 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 2 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 3 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 4 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 5 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 6 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 7 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 8 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 9 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 10 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 11 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 12 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 13 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 14 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 15 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 16 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 17 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 18 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 19 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 20 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 21 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 22 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 23 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 24 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 25 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 26 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 27 of 28 Listing Image for 130 Kai Malina Pkwy Nr1026 28 of 28

$1,899,000

Honua Kai - Konea NR1026

130 Kai Malina Pkwy Nr1026, Kaanapali

2 Beds 2 Baths 1,285 SqFt Residential MLS® # 410685

Days on Market: 11

Maui Westside Properties

Listing Image for 50 Puu Anoano St 4203 1 of 48 Listing Image for 50 Puu Anoano St 4203 2 of 48 Listing Image for 50 Puu Anoano St 4203 3 of 48 Listing Image for 50 Puu Anoano St 4203 4 of 48 Listing Image for 50 Puu Anoano St 4203 5 of 48 Listing Image for 50 Puu Anoano St 4203 6 of 48 Listing Image for 50 Puu Anoano St 4203 7 of 48 Listing Image for 50 Puu Anoano St 4203 8 of 48 Listing Image for 50 Puu Anoano St 4203 9 of 48 Listing Image for 50 Puu Anoano St 4203 10 of 48 Listing Image for 50 Puu Anoano St 4203 11 of 48 Listing Image for 50 Puu Anoano St 4203 12 of 48 Listing Image for 50 Puu Anoano St 4203 13 of 48 Listing Image for 50 Puu Anoano St 4203 14 of 48 Listing Image for 50 Puu Anoano St 4203 15 of 48 Listing Image for 50 Puu Anoano St 4203 16 of 48 Listing Image for 50 Puu Anoano St 4203 17 of 48 Listing Image for 50 Puu Anoano St 4203 18 of 48 Listing Image for 50 Puu Anoano St 4203 19 of 48 Listing Image for 50 Puu Anoano St 4203 20 of 48 Listing Image for 50 Puu Anoano St 4203 21 of 48 Listing Image for 50 Puu Anoano St 4203 22 of 48 Listing Image for 50 Puu Anoano St 4203 23 of 48 Listing Image for 50 Puu Anoano St 4203 24 of 48 Listing Image for 50 Puu Anoano St 4203 25 of 48 Listing Image for 50 Puu Anoano St 4203 26 of 48 Listing Image for 50 Puu Anoano St 4203 27 of 48 Listing Image for 50 Puu Anoano St 4203 28 of 48 Listing Image for 50 Puu Anoano St 4203 29 of 48 Listing Image for 50 Puu Anoano St 4203 30 of 48 Listing Image for 50 Puu Anoano St 4203 31 of 48 Listing Image for 50 Puu Anoano St 4203 32 of 48 Listing Image for 50 Puu Anoano St 4203 33 of 48 Listing Image for 50 Puu Anoano St 4203 34 of 48 Listing Image for 50 Puu Anoano St 4203 35 of 48 Listing Image for 50 Puu Anoano St 4203 36 of 48 Listing Image for 50 Puu Anoano St 4203 37 of 48 Listing Image for 50 Puu Anoano St 4203 38 of 48 Listing Image for 50 Puu Anoano St 4203 39 of 48 Listing Image for 50 Puu Anoano St 4203 40 of 48 Listing Image for 50 Puu Anoano St 4203 41 of 48 Listing Image for 50 Puu Anoano St 4203 42 of 48 Listing Image for 50 Puu Anoano St 4203 43 of 48 Listing Image for 50 Puu Anoano St 4203 44 of 48 Listing Image for 50 Puu Anoano St 4203 45 of 48 Listing Image for 50 Puu Anoano St 4203 46 of 48 Listing Image for 50 Puu Anoano St 4203 47 of 48 Listing Image for 50 Puu Anoano St 4203 48 of 48

$750,000

Masters 4203

50 Puu Anoano St 4203, Kaanapali

1 Bed 1 Bath 901 SqFt Residential MLS® # 410676

Days on Market: 12

Keller Williams Realty Maui-Ki Cell: 808-344-3584

View 6 More Listings

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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