Wailea-Makena Ski Holidays 2025

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Top flight + Ski hotel deals in Wailea-Makena

Price found within the past 48 hours. Click for updated prices.

AEI at Kaanapali Shores

AU$1,660

per person

17 Oct - 22 Oct

found 1 day ago

Return direct flight included

Brisbane (BNE) to Kahului (OGG)

8.8/10 Excellent! (436 reviews)

Clean, comfy,friendly staff, close to stores and beaches

Reviewed on 16 Sept 2025

Royal Lahaina Resort & Bungalows

AU$1,784

per person

17 Oct - 22 Oct

found 1 day ago

Return direct flight included

Brisbane (BNE) to Kahului (OGG)

8.4/10 Very Good! (1,425 reviews)

Beautiful view and area - walkable things to do - great valet workers - valet $45 a day / but: Bird poop everywhere at tables and ledge and birds by food on tables at breakfast - unsanitary old food breakfast/ tasteless expensive dinner / Broken umbrellas - very outdated facility - bathroom sink in kitchen - no microwave Only cleaned room once - had to keep calling for things like coffee, towels, toilet paper/ very little supplies -

Reviewed on 16 Sept 2025

The Whaler Resort Kaanapali Beach

Save 100% on your flight

AU$2,074

per person

17 Oct - 22 Oct

found 1 day ago

Return direct flight included

Brisbane (BNE) to Kahului (OGG)

9.6/10 Exceptional! (226 reviews)

Spacious with everything you could possibly need on an extended stay. Couldn’t ask for more. Only negative was having to leave after 5 nights because we had to go home.

Reviewed on 17 Sept 2025

Montage Kapalua Bay

Save 100% on your flight

AU$4,576

per person

17 Oct - 22 Oct

found 1 day ago

Return direct flight included

Brisbane (BNE) to Kahului (OGG)

9.8/10 Exceptional! (201 reviews)

I liked everything except the dining service. The staff was unfriendly and rude. They should not work there.- they kept us in the bar in excess of 15 minutes even after 4 tables had been open We had to walk over to tell them that tables had been open.

Reviewed on 4 Mar 2025

Hyatt Regency Maui Resort & Spa

AU$2,693

per person

17 Oct - 22 Oct

found 1 day ago

Return direct flight included

Brisbane (BNE) to Kahului (OGG)

9.4/10 Exceptional! (1,002 reviews)

A great place to relax and forget about your daily problems.

Reviewed on 13 Sept 2025

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5* Ski holidays in Wailea-Makena

Price found within the past 48 hours. Click for updated prices.

The Ritz-Carlton Maui, Kapalua

AU$3,257

per person

17 Oct - 22 Oct

found 1 day ago

Return direct flight included

Brisbane (BNE) to Kahului (OGG)

9/10 Wonderful! (1,008 reviews)

I really liked the location of the property. However, I didn’t enjoy the beach as it was very windy and not suitable for swimming with my toddler. The windy conditions could be better managed in the pool areas. The jacuzzis tended to get very crowded in the evenings, mostly with solo visitors and intoxicated individuals, making it uncomfortable to enjoy with my wife. Additionally, I felt pressured by the restaurant staff to leave tips. When I didn’t tip, they refused to serve me. One server from the lobby lounge, named Susan, even confronted me demanding at least a 20% tip for bringing only two cocktails, explaining that the hotel doesn’t pay her hourly. This experience really ruined my mood. Lastly, I found the restaurants to be overpriced.

Reviewed on 12 Sept 2025

Montage Kapalua Bay

Save 100% on your flight

AU$4,576

per person

17 Oct - 22 Oct

found 1 day ago

Return direct flight included

Brisbane (BNE) to Kahului (OGG)

9.8/10 Exceptional! (201 reviews)

I liked everything except the dining service. The staff was unfriendly and rude. They should not work there.- they kept us in the bar in excess of 15 minutes even after 4 tables had been open We had to walk over to tell them that tables had been open.

Reviewed on 4 Mar 2025

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What kind of ski holiday packages are available in Wailea-Makena?

Expedia offers a wide variety of ski holiday packages. To find out what packages are currently available, just search Expedia for Wailea-Makena ski packages 2025 and start planning your next ski trip.

How can I book a ski holiday in Wailea-Makena with Expedia?

Go to the search bar and select “Packages”. Then, choose your destination and the dates of your stay, and browse the list of Wailea-Makena ski packages to find your perfect ski holiday.

Are ski holidays in Wailea-Makena suitable for families?

Wailea-Makena ski holidays can be a great option for families. You can enrol your children in skiing lessons if they’re beginners or spend the days on the slopes with them if they’re already experienced skiers. If your children are too young to ski themselves, look for family-friendly accommodation that offers childcare services and activities for non-skiing family members.

What’s the best way to plan a skiing holiday in in Wailea-Makena?

Planning a ski holiday to Wailea-Makena couldn’t be simpler. Just choose your destination and when you want to go, and Expedia will take care of the rest. Once you’ve selected where and when you want to go, Expedia will provide you with several ski packages for that time and place for you to choose from.

What are some tips for choosing a ski package in in Wailea-Makena?

Before searching for ski packages to Wailea-Makena, define your priorities. Are you looking for a family-friendly resort, luxury accommodations, budget-friendly options, or specific ski terrain? Knowing your preferences will help you narrow down your choices.

How can I find excellent deals on ski holidays in in Wailea-Makena?

One of the most reliable ways to get a good deal for 2025 is to book your Wailea-Makena ski holiday well in advance. Resorts often offer early booking discounts, and you’ll have a wider selection of accommodations to choose from.

How can I grab last-minute ski holiday deals in Wailea-Makena?

Just enter your dates and see what’s available. This way you might be able to nab some great last-minute Wailea-Makena ski packages.

Are pet-friendly ski holiday packages available in Wailea-Makena?

To find pet-friendly Wailea-Makena ski packages in 2025, once you’ve entered your dates, use the filters on the left and select “Pet-friendly” under “Amenities” and the pet-friendly ski resort packages will show up.

How can I find great weekend ski holiday packages in Wailea-Makena?

Enter your weekend dates and search Expedia’s Wailea-Makena ski trip packages to find the ones that are available for the weekend of your choice. You can sort by price to find Wailea-Makena ski holidays that suit your wallet.

How can I find the cheapest ski holidays in in Wailea-Makena?

Once you’ve entered your travel dates, use the sort by filter at the top right to sort by price and find Wailea-Makena ski holidays that won’t break the bank. Plus, booking well in advance can help you find cheaper rates. Be sure to check out Expedia’s Wailea-Makena ski packages including flights as you could save money by booking everything together.

Why should I book a ski holiday package in Wailea-Makena with Expedia?

Expedia lets you bundle up your stay, flight, and car rental for some cool discounts on Wailea-Makena ski packages that will have you carving through the powder without burning a hole in your pocket.

Can I cancel my ski holiday booking in Wailea-Makena with Expedia?

Yes, numerous Wailea-Makena ski packages offer free cancellation, giving you the freedom to put the brakes on your trip in the event of unforeseen circumstances.