Christmas in Maui is a magical time. Here, instead of bundling up in winter jackets, you’re donning your beach apparel. In place of shivering snowmen, you’re crafting glowing sand sculptures. And where your evergreens typically stand, adorned with baubles of red and green, you’ll find a wonderland of lighted palm fronds glowing against a Hawaiian sunset. Doesn’t spending the holidays in Maui sound enchanting?
Beyond the general atmosphere, there are plenty of holiday events in Maui that will help usher in the season. From turkey trots to meeting Santa, there’s an itinerary full of holiday cheer waiting for you.
When it comes to finding the perfect vacation home for these events, Maui Condo has you covered with excellent options that put you close to all the action!
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In this blog:
- Thanksgiving Turkey Trot and Kauhale Makai 512
- Vacation Close to Santa at Grand Champions 033
- Holiday Entertainment Near Leinaala 410
- A Calendar of Fun at Grand Wailea
- Whale Watching in West Maui
- Book Your Maui Holiday Vacation Directly With Maui Condo
Thanksgiving Turkey Trot and Kauhale Makai 512
Is running a holiday tradition in your family? Don’t worry, you don’t have to skip it this year! You can still stay active this holiday season, even on vacation. Every Thanksgiving, runners gather at Keokea Park for the Turkey Trot. This beloved family-friendly event invites participants to join together for a fun run-walk to kick off the holiday season.
This year, awards will be given to the runner in the best Thanksgiving-themed costume, so put that creative spirit to work and get ready to trot to the finish line. Awards are handed out to the top three silliest costumes! The race takes place from 7:00 am to 11:30 am, and runners are encouraged to bring a canned good donation for the Maui Food Bank.
Just a short, scenic drive away from Keokea Park is Kauhale Makai 512, your idyllic holiday retreat.
With a queen bed in the master, two twin beds in the second bedroom, and a sofa bed in the living room, there’s plenty of space for up to six guests in this gorgeous two-bedroom condo. Recent updates and thoughtful touches throughout will make itfeel like your home away from home!
With a fully equipped kitchen, this condo is perfect for your holiday feast preparation, or you can take advantage of one of the many Maui restaurants that will be serving Thanksgiving dinner.
Featured Amenities:
- Sparkling pool + separate kids’ pool
- Hot tub for evening relaxation
- BBQ grills for easy cookouts
- Convenient coin laundry on-site
- Putting green & shuffleboard for fun downtime
Vacation Close to Santa at Grand Champions 033
Christmas officially comes to Maui on November 28th! After a day of turkey and family togetherness comes the full seasonal transition, starting with Santa’s arrival at the Shops at Wailea.
While the full dates and information have not yet been released for 2025, the event repeats the same traditions year after year, so we have a good idea of what it will look like.
The celebration typically begins with a parade from 9 to 10 am, where Maui Classic Cruisers and Street Bikers United Hawaii escort Santa from Kalama Park to the Shops. Following the parade, you can enjoy a traditional Holiday Polynesian Show at the Lower Valley Performance Area from 11 am to noon. Then, wear your Christmas best and get ready for pictures with Santa from noon to 2 pm.
After you’ve shopped ‘til you drop, head home to Grand Champions 033.
Recently remodeled, this two-bedroom, two-bath garden-view condo features brand new furniture throughout, including Jefferson Plush Cal-King mattresses for an unparalleled rest. The primary and guest bedrooms, each with a Cal-King bed, along with a queen sofa sleeper in the living room, allow up to six guests to stay comfortably. This ground-floor unit, with tile in the common areas and carpet in the bedrooms, is perfect for relaxing and entertaining. A new mini-fridge and microwave in the primary bedroom add an extra touch of convenience.
The condo's lanai has been updated with a new table and four chairs, expanding outdoor seating to seven, ideal for enjoying Wailea's peaceful evenings.
Featured Amenities:
- Two pools and two hot tubs
- In-unit laundry
- Close to Wailea’s renowned golf courses
Holiday Entertainment Near Leinaala 410
If you’re visiting in early December, you must go see a show at Maui's ProArts Playhouse. Every year, they put on several Christmas and holiday-themed shows that are sure to get you in the festive spirit! While their shows for 2025 aren’t out just yet, we can assure you that their lineup is always impressive. Keep an eye on their site and make sure to snag tickets when they become available!
Not far from the ProArts Playhouse, you’ll find Leinaala 410.
This one-bedroom unit combines comfort and scenic beauty, featuring a queen bed and a sofa bed in the living room, allowing you to comfortably host up to four guests. The fully equipped kitchen and expansive lanai are ideal for unwinding and enjoying ocean views, while the grounds feature a green belt that leads to a beautiful walking beach perfect for leisurely strolls.
Featured Amenities:
- Modern appliances
- Oceanfront views
- Easy beach access
A Calendar of Fun at Grand Wailea
The Grand Wailea turns into a festive paradise throughout December, hosting a series of events that bring the holiday spirit to life in Maui. Here are the highlights:
- Tree Lighting Ceremony | December 15th, 6 PM– Join locals and fellow visitors in the lobby for live entertainment that culminates with a countdown to the spectacular tree lighting.
- Holiday Marketplace | December 15th, 4 PM to 8 PM – Find last-minute gifts or unique Hawaiian-made souvenirs.
- Santa’s Arrival on Outrigger | December 24th, 9 AM – Head to Wailea Beach to witness a unique Maui-style Christmas Eve as Santa and Mrs. Claus trade the sleigh for a traditional outrigger canoe for their grand arrival.
- Christmas Day Brunch | December 25th, 11 AM to 2 PM – Don’t feel like cooking on Christmas? No problem! This delicious brunch menu includes a seafood bar, Christmas classics, and other holiday staples.
After all the holiday fun, it’s time to tuck in and await Christmas morning at Kihei Surfside 307.
This oceanfront one-bedroom condo offers breathtaking views of the Pacific, the West Maui Mountains, and the island of Lanai. The balcony, furnished for optimal relaxation, is the perfect spot to enjoy the cool ocean breeze and Maui's stunning sunsets. Inside, the natural light enhances the newly installed tile floors and the recently remodeled kitchen, complete with cherry wood cabinets, granite countertops, and new appliances.
Featured Amenities:
- Queen-sized bed
- On-site shuffleboard and putting green
- Glass door walk-in shower
Whale Watching in Maui
No trip to Maui during the holiday season is complete without booking a whale-watching tour so you can marvel at the majestic humpback whales who’ve made the long trek back to our warm Pacific waters. For an educational and enjoyable experience, check out PacWhale Eco-Adventures. Their skilled marine naturalists lead you on an exciting tour, bringing you face-to-face with nature’s giants.
Learn More About Whale Watching in Maui
For a convenient home base in West Maui, book your vacation at Aston Maui Kaanapali Villas 148.
This newly remodeled ground-floor studio at Maui Ka’anapali Villas makes island living simple and carefree. Just steps from the pool and a short stroll to the beach, it’s a perfect spot for couples or small families. Inside, you’ll find a king bed, queen sofa bed, and a cozy kitchenette with everything you need for a holiday meal or festive morning coffee. Sliding doors open to a private garden-view lanai, where you can relax with Maui breezes and tropical surroundings, even in the winter time! With easy access to the resort’s pools, beach, and dining, this studio serves as the perfect holiday getaway.
Featured Amenities:
- 11 acres of tropical gardens
- Fitness center
- Resort WiFi
Book Your Maui Holiday Vacation Directly With Maui Condo
This holiday season, give the gift of a unique experience and book a trip to beautiful Maui. With unbeatable weather, picture-perfect beaches, and a range of holiday events, it’s guaranteed to be a trip you’ll remember forever. When choosing your Maui vacation rental, be sure to book directly with us for the best prices and unbeatable service. We can’t wait to welcome you (vacation) home for the holidays!