Posted on: September 25, 2025
Thinking of a holiday escape in Maui between October and January? Wonderful idea! But many travelers ask: “What will the weather be like? Will it rain? What should I pack?”
Good news: you’re headed someplace warm, beautiful, and vibrant, even during the “holiday season.” And when you stay at Wailea Ekahi Village, you’ll be well‑placed on Maui’s sunnier south shore for comfort, convenience and unforgettable views.
In this guide you’ll get:
- A month‑by‑month overview of weather from October through January
- Helpful packing and rain‑tips so you’re prepared
- Why staying at Wailea Ekahi Village is a smart choice for the holiday season
- What to do—even if there are a few showers
Maui Holiday Weather at a Glance
Before we dive into each month, here’s a quick snapshot of what to expect:
- Daytime temperatures remain warm (typically mid‑to‑upper 70s to mid‑80s°F) even in fall/winter.
- Rainfall begins to increase after November, but much of the south leeward side of Maui (including Wailea) remains drier than the windward sides.
- Ocean stays warm for swimming and snorkeling.
- Fewer crowds in October and early November.
- Holiday season (mid‑December through New Year’s) sees more visitors and festive energy.
Month‑by‑Month Weather & Travel Tips
October in Maui
Weather:
- Highs around 85°F, lows in the low 70s°F.
- Rainfall is still low (approx. 1‑2″), especially in south Maui.
Why go now:
- Shoulder season: fewer crowds, better rates, pleasant weather.
What to pack:
- Beachwear + one light layer for evenings.
- Reef‑safe sunscreen, sunglasses, swim gear.
Tip:
- A great time for spontaneous bookings and flexible itineraries.
November in Maui
Weather:
- Highs in 80s°F, lows mid‑60s to high‑60s°F.
- Rain begins to creep in, but south‑shore microclimate remains favorable.
Why go now:
- Prime time for early holiday trips, honeymoons, or quiet family stays before peak crowds hit.
What to pack:
- Swimsuit for the day, light jacket for cooler nights.
- Compact umbrella or light rain shell just in case.
Tip:
- Consider booking holiday‑week stays early—good dates go fast.
December in Maui
Weather:
- Highs around 82–83°F, lows near 65°‑68°F.
- Rainfall increases (approx. 3‑4″ or more) but leeward resorts like Wailea still enjoy many sunny days.
Why go now:
- Festive mood, holiday decorations, special dinners, whale‑watching begins (December–April).
What to pack:
- Smart casual attire for a holiday dinner.
- Lightweight sweater or long‑sleeve for evening breezes.
- Quick‑dry items and a rain‑cover for your daypack.
Tip:
- Book accommodations, car rentals and dinner reservations early. Staying at a well‑located condo gives you flexibility and comfort.
January in Maui
Weather:
- Highs near 80°F, lows around 63°‑65°F.
- Rain is still present but mostly short showers; water remains warm for snorkeling.
Why go now:
- Whale‑watching season is ramping up. Quiet days after New Year’s give the island a calm, relaxing vibe.
What to pack:
- Light jacket for early mornings or sail excursions.
- Think swim suit + optional light layer for the summit or sunset strolls.
Tip:
- If you want a mix of adventure + relaxation, January is a sweet spot for value and experience.
Dealing with Rain (Without Letting It Ruin Your Trip)
Even in leeward zones like Wailea, occasional showers happen. Here’s how to stay ahead:
- Pack a compact umbrella or light rain shell—it doesn’t have to be heavy.
- Use rainy moments to switch up activities:
- Visit the Maui Ocean Center in Maʻalaea for indoor marine‑life fun.Enjoy a couples massage or spa treatment.
- Grab lunch at a beach‑side cafe, then relax in your condo’s lanai with a book and ocean breeze.
- Stay on the south shore (Wailea/Kihei) for fewer rainy‑day disruptions; north/windward sides tend to get more rain.
- Book flexible experiences (some tours allow re‑scheduling) and keep a mix of indoor and outdoor options on your itinerary.
Where to Stay & What to Do for the Holidays
Why Choose Wailea Ekahi Village
- Located on Keawakapu Beach and along the scenic Wailea Beach Path—easy access to sand, sea and strolls.
- Spacious condo rentals with full kitchens, private lanais, and resort‑style yet relaxed amenities.
- Four pools, tropical gardens and a calm low‑density layout make it ideal for families, couples, or longer stays.
- Walkable to restaurants, shopping and nature trails—perfect for holiday getaways or winter escapes.
- Holiday stays at a condo give you flexibility: cook your own meal, relax on your lanai during a shower, enjoy firework views and public events with ease.
What to Do During Holiday Season
- Whale‑watching cruises (especially starting December) — a magical experience off South Maui’s coast.
- Sunrise at Haleakalā National Park followed by brunch and chill at your condo.
- Strolls on Wailea Beach Path with sunset views and ocean breeze.
- Beach days, snorkeling (weather permitting) or relaxed pool‑side time when showers roll in.
- Holiday limelight: Special dinners, beachfront luaus, local events and lights.
- “Room day”: On a rainy afternoon, cook together in your kitchen, sip wine on your lanai, and soak in the calm.
Booking Tips for a Smooth Holiday Trip
- Reserve early, especially for December or New Year’s stays.
- Check rates + date flexibility: January and early February may offer better value.
- Choose accommodations with flexibility and comfort, like a condo rental, so rainy days don’t limit your enjoyment.
- Pack smart (see above) and keep a flexible mindset, some rain means more time for connection, less rush.
- Focus on location: Staying in Wailea gives you one of the sunniest, most convenient bases on Maui.
Start Planning Today
Holiday travel to Maui doesn’t mean rain, cold or compromise; it means warm breezes, golden sunsets, festive nights, and a home base that welcomes you every day. At Wailea Ekahi Village, you’re in the perfect spot on the island’s sunny south shore, with all the comforts of home and the magic of Maui built in.
So pack your swimsuit, one light layer, maybe an umbrella just in case, and get ready for an unforgettable holiday escape. Whether you’re here in October, November, December or January, Maui is ready—are you?
Explore rentals at Wailea Ekahi Village now and start planning your holiday getaway.