Maui Winter Vacation for Canadians

Heritage Vacation Homes

Vacation Rental Owners Welcome You to Hawaii to Escape Canadian Winters

Your Maui Winter Vacation Awaits

We’ve always loved the beauty and serenity of Maui, Hawaii, and we’re excited to share that experience with our Canadian guests.

Whether you’re dreaming of:

  • Escaping the cold Canadian winter for a tropical getaway
  • Looking for a peaceful retreat to recharge
  • Booking directly with us—the owners of Heritage Vacation Homes—means a personalized, stress-free experience.

No booking agents. No third parties.

Just genuine, heartfelt service directly from our family to yours, making your vacation as seamless as possible.

Book Your Winter Vacation
Warm Beaches While the Snow Falls Back Home

Why Maui Is the Perfect Winter Escape for Our Canadian Guests:

As beautiful as Canadian winters are, the cold sometimes makes you crave a break. For those seeking hot destinations in January, Maui’s 80°F afternoons are a perfect escape from -10°C mornings. Ready to switch from snowshoes to flip-flops?

Here are some top reasons our guests love a winter Maui vacation:

  • Direct Flights: Convenient direct flights from Vancouver and Calgary make it easy to reach Kahului (OGG), Maui without layovers. A nonstop flight from Vancouver takes just about 6 hours! Check out Air Canada’s flight options for the best routes to escape the winter chill. 
  • Warm, Tropical Weather: Whether you’re snorkeling with sea turtles or playing pickleball in the refreshing ocean breeze, you’ll be thinking, “I’m so glad to be in Hawaii,” as the warmth melts away any lingering winter chill.
  • Book Direct, Stay Local: When you book directly with us, you’re not just another guest. We’ll share our favorite local spots and ensure you feel right at home. Lara, your host, is always available—just a quick text or call away if you need anything during your stay.
  • Peak Whale-Watching Season: From January to March, it’s prime time to spot humpback whales—and you can watch them right from the comfort of your rental!
Air Canada plane wing with a red maple leaf logo against a stunning sunset sky, blending deep blue with soft pink hues.
Mom, Dad, and kid snorkeling in crystal clear waters, wearing colorful snorkel gear and smiling.
Ultimate Whale watching zodiak boat keeping it's distance as it views a humpback whale splashing it's tale in the ocean.

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Don’t miss out on exclusive deals and insider tips just for our Canadian visitors. Sign up for our newsletter to save $100 on your next stay and get the latest updates on travel, activities, and promotions.

Why Book Direct With Heritage Vacation Homes

Booking directly with us isn’t just about securing a rental—it’s about peace of mind and a personal touch! We know booking with an owner can feel daunting if it’s your first time, but we make it easy:

  • Personal Touch: No third parties—Lara, your host, is available 24/7 for any questions or assistance.
  • Local Expertise: We provide insider tips on the best snorkeling spots, restaurants, and more.
  • Stress-Free Experience: From booking to check-out, we handle everything, ensuring your trip is seamless.
View Our Maui Guide
Woman holding a pink and purple plumeria flower while she wears a white Hawaiian dress.
Aerial view of Maui coastline in front of the Wailea Makena Surf Resort condo complex. Clear teal waters.

Discover Makena Surf C-107

Nestled in a peaceful resort, Makena Surf C-107 offers everything you need for an unforgettable Maui getaway:

  • Private beach access for tranquil morning walks.
  • Breathtaking sunset views from your lanai.
  • Whale watching right from your rental during peak season.

Ready to escape the cold and experience the magic of Maui?

Learn More About Makena Surf C-107
Planning your trip to the U.S. from Canada?

Canadian Travel Tips:

We’ve gathered some essential information to help make your journey seamless. While we don’t handle the travel requirements directly, you can find everything you need on the official GoHawaii.com.

Travel Requirement

For a smooth entry into Hawaiʻi, remember that Canadian citizens (yes, including the little ones!) need a valid passport or NEXUS card to fly into the islands. It's also a good idea to double-check that your passport hasn’t expired—especially if it’s been tucked away since your last big adventure!
Learn More About Requirements

Flight Tips:

Canadians can hop on direct flights to Kahului (OGG) from Vancouver with Air Canada or WestJet. Plus, WestJet has seasonal direct flights from Calgary on Sundays, Wednesdays, Fridays, and Saturdays during the winter. If you're coming from Toronto, Montreal or other airports just a heads up—you’ll need a connecting flight, so it’s a good idea to book early for the best deals.
View Air Canada Specials

Length of Stay:

Canadians typically enjoy a stay of up to six months in the U.S., making it ideal for a long work-from-home vacation. If you’re looking for the ideal spot, check out Makena Surf C-107! We have high-speed internet and stunning views, allowing you to experience the best places to work remotely for a few weeks or more.
View Makena Surf C-107

Currency Exchange Tip:

If you're looking for better rates, try using local banks or ATMs to swap your CAD for USD. It's also worth checking whether it's cheaper to exchange money in the U.S. or Canada since rates can differ. If you're using cash, be sure to havePlus, using a credit card that doesn't have foreign transaction fees can save you from those pesky extra charges while traveling!
Find More Tips Here
We’ve had the pleasure of welcoming so many wonderful Canadian travelers into our homes.

What Our Canadian Guests Are Saying:

"A beautiful place to stay. Wonderful view. Unit fully appointed with all essentials and extras. Really comfortable. Always a quick and helpful response from owner. Highly recommended!"
Stuart R
Makena Surf C-107
Let’s Plan Your Winter Escape Together

At Heritage Vacation Homes, we’re not just offering a place to stay; we’re here to make your Canadian winter getaway unforgettable. With personalized service, insider tips, and seamless booking, we can’t wait to welcome you!

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