Wailea
Hotel Wailea Maui
In Wailea. Guests score it 9.2 out of 10 across 122 Booking.com reviews.
- Top rated
★ 9.2 guest score from 122 Booking.com reviews · Many rooms include free cancellation
Last updated: October 2026
Maui — Traveler Guide
The best-rated 4- and 5-star hotels in Maui for a Christmas trip, with this year's festive events, December weather and the best areas to stay.

Quick Answer
Our top pick for Christmas in Maui is Hotel Wailea Maui in Wailea, rated 9.2 from 122 Booking.com reviews. Hyatt Regency Maui Resort & Spa is a strong alternative at 8.5.
7 places · Checked October 2026
Wailea
In Wailea. Guests score it 9.2 out of 10 across 122 Booking.com reviews.
★ 9.2 guest score from 122 Booking.com reviews · Many rooms include free cancellation
Kaanapali Beach Resort
In Kaanapali Beach Resort. Guests score it 8.5 out of 10 across 209 Booking.com reviews.
★ 8.5 guest score from 209 Booking.com reviews · Many rooms include free cancellation
Wailea
In Wailea. Guests score it 9.1 out of 10 across 107 Booking.com reviews.
★ 9.1 guest score from 107 Booking.com reviews · Many rooms include free cancellation
In Wailea. Guests score it 8.7 out of 10 across 260 Booking.com reviews.
★ 8.7 guest score from 260 Booking.com reviews · Many rooms include free cancellation
Kaanapali
In Kaanapali. Guests score it 8.9 out of 10 across 423 Booking.com reviews.
★ 8.9 guest score from 423 Booking.com reviews · Many rooms include free cancellation
Kaanapali Beach Resort
In Kaanapali Beach Resort. Guests score it 8.9 out of 10 across 163 Booking.com reviews.
★ 8.9 guest score from 163 Booking.com reviews · Many rooms include free cancellation
Kaanapali Beach Resort
In Kaanapali Beach Resort. Guests score it 8.8 out of 10 across 164 Booking.com reviews.
★ 8.8 guest score from 164 Booking.com reviews · Many rooms include free cancellation
About This Guide
Christmas on Maui is warm, with Santa arriving by outrigger canoe or catamaran at beach resorts, holiday movie nights and hula and music at shopping centres. December is the start of the humpback whale season, and whales are often seen from shore. West and South Maui (Kaanapali, Kihei, Wailea) are mostly dry and sunny, though showers are brief and can be heavier on the windward side.
Dates and times change from year to year, so check the organiser's listing before you travel.
December highs are around 80 to 85°F (27 to 29°C) with lows around 66 to 69°F (19 to 21°C) in the leeward resort areas, with mostly sunny days and brief showers.
How we picked: the 7 hotels in this guide are 4- and 5-star hotels and resorts in Maui with the strongest Booking.com guest scores, weighted by how many reviews they have. Scores and review counts were checked in October 2026.
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Common Questions
Yes. Humpback whales migrate to Hawaii each winter, with sightings building from late autumn and peaking in the early months of the year. They can often be seen from beaches in Kaanapali, Kihei and Wailea.
Warm, with highs around 80 to 85°F (27 to 29°C) on the leeward coasts. Showers are brief, and the windward side is wetter. The ocean is warm enough to swim, but winter swells can make some beaches rough.
Lahaina town is still recovering from the 2023 fire. Kaanapali and other West Maui resort areas remain open, and some Lahaina shopping centres have reopened. Check current county guidance and road access before planning visits.
Hotel Wailea Maui has the highest score of the places in this guide for Christmas: 9.2 out of 10 from 122 Booking.com reviews (checked October 2026).
Prices and availability change daily. Lock in the best rate by booking early — most of our top picks offer free cancellation.
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