• This field is for validation purposes and should be left unchanged.

Maui Winter Rentals

Escape the cold and spend your winter months in a tropical paradise. With consistently warm temperatures throughout the winter, pristine white sand beaches, and sunny blue skies, the swaying palms are beckoning for a winter getaway to Maui. While elsewhere coats, hats, and mittens are being donned, winter in Maui remains warm and balmy during the day with cool, refreshing breezes at night. Pack your summer gear and head to Maui to bask in the warmth! Be sure to choose one of Quam Properties Hawaii, Inc’s best winter rentals in Maui for your next getaway to make it a vacation to remember.

Book our Maui Winter Rentals Below!

Please click here to disable map search and reload all the units.

Well-Appointed Winter Rentals in Maui

Our winter rentals in Maui offer everything you’ll need for an enjoyable Maui vacation. From cozy one bedrooms perfect for a romantic getaway, to multiple bedrooms and multiple bathrooms ideal for the whole family or for small groups, our Maui winter rentals can accommodate a variety of travelers. Whether you’re hoping to wake and sleep to the sights and sounds of the crashing waves, or to simply find a chic, budget-friendly place to stay, our Maui winter rentals can suit an assortment of preferences and budgets.

Book one of our waterfront Maui winter rentals to enjoy stunning ocean views from the privacy of your home away from home. Especially in winter, there’s a good chance you might catch sight of a whale spout from your lanai as they splash and play in the warm Hawaiian waters. When you’re ready to venture out, you won’t have to go far to find entertainment. Many of our winter rentals offer onsite pools, perfect for lazing in the sunshine. Our oceanfront rentals will put you just steps from postcard perfect white sand beaches!

Special Activities for Your Maui Winter Getaway

If you’re planning a trip to Maui over the holidays, there are plenty of activities available to get the whole family in the holiday spirit. Special holiday pop-up craft fairs are great places to pick up gifts or to treat yourself to something special that was handcrafted on the island. Santa even makes his way to the island, although it’s frequently by outrigger canoe or jet ski rather than by sleigh!

Winter is also a great time to catch sight of the many whales that migrate from Alaska to the warm Maui waters over winter. Whale watching season falls from mid-December to mid-May, making winter an ideal time to visit Maui. Taking one of the many boat tours available allows you to see these gentle giants up close and personal, as well as enjoying views of Maui’s magnificent coastline. Some companies even offer a whale sighting guarantee, or you’ll enjoy an additional boat tour for free! In addition to admiring the beauty of the fascinating humpback whale (and landing some amazing photo opportunities!), you’ll also learn more about their movements and connections with Hawaii from knowledgeable guides. Depending on the tour you choose, opportunities for offshore snorkeling and dolphin sightings may be possible additional perks!

During winter months on Maui, the surf tends to be up on North Shore and calmer on the south shore. Even if you’re not an avid surfer, heading to the North Shore to watch some of the huge swells come in or to observe pro surfers in their element can be an awe-inspiring experience. Honolua Bay and Hookipa Beach are hot spots for big wave surfing in winter. Just east of Hookipa Beach is Peahi, also known as Jaws. Surfers are towed in by jet skis during massive swells on this world-renowned surf break! Of course, while these breaks are reserved for the pros, there are other milder destinations for beginning surfers to try their hand at this favorite local sport. Outfitters such as Maui Wave Rider Lahaina offer surf lessons perfectly suited for all levels, beginners to advanced. After a short 10- to 15-minute lesson on land, the rest of your time will be spent in the water building confidence as your instructor assists you in riding the waves!

Choose one of the many Hawaii winter rentals offered by Quam Properties for your tropical winter getaway!

Contact Us for Stunning Hawaii Winter Rentals

At Quam Properties, we handpick the highest quality vacation rentals on the beautiful island of Maui. Not only are we selective in our process, but we are also highly attentive to detail to ensure that our properties are always maintained to a flawless level. Our vacation rentals are situated across the sunny northwest coast of Maui, including the areas of Wailea, Kihei, Lahaina, Kaanapali, Kahana, Napili, and Kapalua. Staying in one of these rentals will put you in perfect proximity for enjoying some of the island’s best beaches, shopping, restaurants, and world-class golf courses. Many of our rentals offer stunning oceanfront views, full kitchens, resort-like pools, and everything you’ll need for an unforgettable Maui getaway. Make your reservation today by booking online or calling our office at 808-665-1315.