Holiday Season on Maui: Christmas Events, Things to Do & Real Estate in Kihei, Wailea & Makena

The holiday season on Maui brings warm sunshine, festive island events, and some of the most beautiful weather of the year—especially along the sunny coastline of Kihei, Wailea, and Makena. I was talking to a gentleman from Nevada, he was mentioning how cold it gets this time of year with the wind blowing off the mountains. Coming to Maui has always been his go to getaway for some sunshine and beaches.

December through early March is one of the best times to experience South Maui beaches, winter whale watching, and vibrant holiday celebrations. It’s also a popular season for visitors exploring Kihei homes for sale, Wailea resort condos, and Makena oceanfront luxury real estate. I been hearing that the hotels are looking pretty booked coming into the winter season.

Holiday Getaway in Kihei — Beaches, Events & Local Flavor

Kihei comes alive during the Christmas season. Families enjoy the warm, calm ocean conditions at Kamaole I, II, and III—ideal for swimming, snorkeling, and stand-up paddling. Whale activity peaks this time of year, making it common to see breaching whales from shore or on a Christmas whale-watching cruise departing Maalaea Harbor. I recommend the Trilogy Excursions.

Holiday events in Kihei often include, Christmas craft fairs, outdoor markets, food trucks, and live music at Kalama Park. Visitors can enjoy festive dining at Café O’Lei, Coconut’s Fish Café, or beachside sunset dinners along South Kihei Road. For long-term visitors or future buyers, Kihei offers a variety of affordable Maui condos, oceanfront Kihei properties, and vacation-friendly neighborhoods close to beaches and shopping. If you are looking for something more country, Northshore, tropical, and peaceful. You should check out Pineapple Cottage on Maui’s Northshore.

Wailea Holiday Season — Luxury, Shopping &

Festive Experiences

Wailea is one of the island’s most magical places during the holidays. The Shops at Wailea host a series of seasonal events, including: You can check Shops at Wailea calendar events on my website. 

• Tree lighting ceremonies. The hotels do an amazing job capturing the Christmas spirit. Even if you’re not staying in hotel. They do offer excellent dining, or maybe a glass of wine and a Hawaiian sunset works.

• Live Hawaiian music and hula. Check the Shops at Wailea for musical events. They do bring in top entertainment from around Hawaii.

• Holiday keiki activities- check with the local hotels on schedule events.

• Artisan craft markets. Some of the hotels have Pop-up markets featuring local artisit.

• Photos with Santa in Aloha wear, make sure and visit the Shops at Wailea, always something going on.

Resort hotels like the Grand Wailea, Fairmont Kea Lani, and Wailea Beach Resort offer Christmas brunches, holiday luaus, and elegant New Year’s Eve celebrations. Visitors enjoy walking the Wailea Beach Path, golfing at Wailea Blue or Gold Course, or spending Christmas morning relaxing at Wailea Beach or Polo Beach.

Winter is also prime time for exploring Wailea luxury real estate, including Wailea Ekahi Village, Wailea Elua, Ho‘olei, Papali Wailea, and gated residential communities like Wailea Golf Vistas. Many buyers fall in love with the resort lifestyle and begin searching for Wailea oceanfront condos, second homes, or investment properties with strong vacation-rental demand.

Makena Holiday Peace — Big Beach, Outdoor Adventures & Exclusive Real Estate

For those seeking a quiet, natural holiday experience, Makena Maui delivers unmatched beauty. Christmas morning swims at Big Beach or snorkeling at Ahihi-Kinau Reserve are seasonal favorites. Visitors often take scenic hikes through La Perouse Bay, explore lava fields, or enjoy sunset picnics overlooking the rugged Makena coastline.

Holiday events are more low-key here, but many visitors attend Wailea’s Christmas activities while staying in Makena for privacy. This area attracts buyers looking for unique Makena oceanfront estates, luxury homes, and rare properties at Makena Place or Black Sands—ideal for those who value space, views, and exclusivity.

Enjoy the Season — And Explore South Maui Real Estate

Whether you’re visiting for Christmas or planning a return trip, the holiday season is one of the best times to discover the lifestyle and real estate opportunities in Kihei, Wailea, and Makena. If you’re interested in South Maui homes, condos, or oceanfront properties, I’ve been selling real estate on Maui for over 30 years and would be happy to help you explore your options. View oceanfront condos for sale in Makena and Wailea Maui.

Wailea Makena Homes For Sale