Wailea-Makena Vacations from $1,189

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Your Wailea-Makena Vacation

Make organizing your next adventure a breeze with a Wailea-Makena vacation package. Whether it's the cuisine, nature or something else that draws you here, our packages will help you discover it all. Can't decide what should come first? Makena is one of the most popular cities to explore during your trip to Wailea-Makena. If you're ready to stop daydreaming and start doing, Expedia will help turn your Wailea-Makena vacation into a reality.

The Latest Wailea-Makena vacation packages

Price found within the past 48 hours. Click for updated prices.
Maui Banyan Vacation Club
Maui Beach Vacation Club
Lumeria Maui Educational Retreat Center
Hotel Wailea Maui
Kihei Surfside - Maui Condo & Home
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Stay near popular Wailea-Makena attractions

Wailea-Makena Hotel Deals

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$742 nightly
The price is $881 total per night from Nov 20 to Nov 21
$881 total
Nov 20 - Nov 21
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
"Ha sido la mejor experiencia"

Reviewed on Oct 28, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
$1,058 nightly
The price is $1,256 total per night from Nov 28 to Nov 29
$1,256 total
Nov 28 - Nov 29
Total with taxes and fees
9.6/10 Exceptional! (1,006 reviews)
"Great stay. The beach was damaged from hurricane but we still enjoyed it and had a great time."

Reviewed on Oct 27, 2026

Fairmont Kea Lani Maui
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
$1,030 nightly
The price is $1,223 total per night from Nov 28 to Nov 29
$1,223 total
Nov 28 - Nov 29
Total with taxes and fees
Four Seasons Resort Maui at Wailea
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Wailea-Makena Vacation Packages

Wailea-Makena Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Kahului Airport (OGG)

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Frequently asked questions

How much does a Wailea-Makena vacation package cost?
A Wailea-Makena vacation package typically costs around $2,800 per adult for a week-long trip. Lower-priced options start around $1,250 per adult, while premium resort packages can reach up to $5,650.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How can I save money on a Wailea-Makena vacation package?
When you bundle, you can save up to 30%*. To save money on a Wailea-Makena package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's included in a Wailea-Makena vacation package?
A Wailea-Makena vacation package lets you combine flights, hotel stays, and rental cars. As a beach destination, Wailea-Makena offers direct beach access at many hotels. Over half of hotels here include free breakfast, and some also offer airport shuttle service to and from Kahului (OGG) airport.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How do I find cheap Wailea-Makena vacation package deals?
The cheapest Wailea-Makena vacation package deals start around $610 per adult for weekend trips. Separately, October typically has the lowest average monthly prices, around $2,170 per adult, for a 6-day trip, and May follows closely at around $2,340 per adult, also for a 6-day trip.

Bundling your flight and hotel can also help reduce the total compared with booking separately. For week-long trips, most Wailea-Makena packages include some savings versus booking separately, typically around $455 per adult. Longer, two-week trips can save even more, often around $595 per adult. Over half of hotels in Wailea-Makena also include free breakfast, which can help stretch your budget further.

Browse cheap vacation packages in Wailea-Makena on Expedia to compare current deals for your preferred dates.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
What is the best time to visit Wailea-Makena?
The best time to visit Wailea-Makena for a vacation package is January through March, which is its most popular period for travelers. January is the peak month for demand, offering a lively atmosphere.

During this time, you can also find events such as the Burn and Wound Care Symposium in January and AHA Instructor Courses In Maui, HI in February, which may add to the local vibrancy. Event dates can change, so confirm the schedule before booking your Wailea-Makena vacation.
What types of vacation packages are available in Wailea-Makena?
Wailea-Makena, known for its beautiful beaches, outdoor activities, and scenic views, offers several types of vacation packages:
  • Beach: Wailea Beach Resort - Marriott, Maui, a 5-star property rated 8.7 out of 10 by travelers, provides direct access to the ocean with an outdoor pool and on-site dining.
  • Family: Four Seasons Resort Maui at Wailea, a 5-star resort rated 8.7 out of 10 by travelers, is a strong choice for families with its kids club, babysitting services, and outdoor pool.
  • Luxury: Grand Wailea Maui, A Waldorf Astoria Resort, a 5-star property rated 8 out of 10 by travelers, offers upscale amenities like a game room, hot tub, and kitchen facilities.
  • Couples: Hotel Wailea, Relais & Chateaux - Adults Only, a 5-star property rated 9.3 out of 10 by travelers, provides a serene adults-only experience with a kitchenette, outdoor pool, and spa.
  • Budget: Aston at the Maui Banyan, rated 7.9 out of 10 by travelers, offers a more economical stay with amenities like a kitchen, kitchenette, and outdoor pool.
Is Wailea-Makena better suited for a beach vacation or a cultural trip?
Wailea-Makena is primarily a beach destination, making it an ideal choice for a beach vacation. The area is known for its beautiful beaches, with most package hotels offering ocean views. Travelers can enjoy stunning stretches of sand like Wailea Beach and Polo Beach, perfect for relaxation and water activities.

A Wailea-Makena vacation package is best suited for those seeking sun, sand, and resort amenities.
Which airport should I use for a Wailea-Makena vacation?
For a Wailea-Makena vacation, the primary gateway is Kahului, HI (OGG), which serves the area and is located on Maui. Travelers can also consider Kailua-Kona, HI (KOA-Kona Intl.) as an alternative, though it is located on a different island and may require additional travel arrangements to reach Wailea-Makena.
What are the top things to do in Wailea-Makena?
A Wailea-Makena vacation offers plenty of opportunities to enjoy the beautiful coastline and outdoor activities:

Browse and book things to do in Wailea-Makena on Expedia.
Are there family vacation packages in Wailea-Makena with kid-friendly amenities?
Wailea-Makena offers family vacation packages with a range of kid-friendly amenities:
  • Four Seasons Resort Maui at Wailea: This 5-star resort, rated 8.7 out of 10 by travelers, features a kids club and babysitting services, making it easy for parents to relax while children are entertained. Travelers often praise the attentive staff and beautiful pool.
  • Fairmont Kea Lani Maui: Rated 9.2 out of 10 by travelers, this 5-star property provides spacious family rooms and both indoor and outdoor pools, with travelers highlighting the well-maintained rooms.
  • Ho'olei Villas at Grand Wailea: With a perfect 10 out of 10 rating by travelers, these 5-star villas offer family rooms and a game room, providing ample space and entertainment for all ages.
  • Aston at the Maui Banyan: Rated 7.9 out of 10 by travelers, this property includes family rooms, kitchens, and kitchenettes, which are convenient for preparing meals, and travelers frequently mention the fantastic staff.
What luxury vacation packages are available in Wailea-Makena?
Wailea-Makena offers a selection of luxury vacation packages centered around high-end resorts:

Browse luxury vacation packages in Wailea-Makena on Expedia for current choices.
What's included in a Wailea-Makena beach vacation package?
Wailea-Makena beach vacation packages typically bundle flights with a stay at a beachfront or beach-adjacent hotel, allowing for easy access to the area's renowned coastline. Hotels like the 5-star Fairmont Kea Lani Maui, rated 9.2 out of 10 by travelers, and the 5-star Wailea Beach Resort - Marriott, Maui, rated 8.7 out of 10 by travelers, often feature outdoor pools and on-site dining options. While the package itself includes flights and accommodation, specific beach activities or water sports are usually arranged separately, though many resorts provide direct beach access for guests to enjoy the ocean.
What is the best time to book a Wailea-Makena vacation package?
Book your Wailea-Makena vacation package around 9 weeks in advance. This gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 4 and 16 weeks out.

from June to August is the most popular months for Wailea-Makena packages, so booking earlier is advisable if you're traveling during these times. If you're planning a spontaneous getaway, Expedia also offers last-minute Wailea-Makena vacation packages.
How many days do you need for a Wailea-Makena vacation?
Most Wailea-Makena vacation packages last around 6 days. This allows ample time to enjoy the area's beautiful beaches, such as Wailea Beach, and explore the scenic surroundings. Week-long stays are the most popular, though some travelers opt for shorter weekend trips or extended two-week stays to fully immerse themselves in this beach destination.
Which Wailea-Makena vacation packages include an ocean view?
Many Wailea-Makena vacation package hotels offer rooms with ocean views, with most package hotels providing this option. For example, the 5-star Fairmont Kea Lani Maui, rated 9.2 out of 10 by travelers, and the 5-star Hotel Wailea, Relais & Chateaux - Adults Only, rated 9.3 out of 10 by travelers, are both located near the coastline and feature ocean-view room categories. While the specific view depends on the room booked, these properties allow travelers to enjoy the stunning Pacific Ocean scenery.
Which Wailea-Makena vacation packages include a mountain view?
Some Wailea-Makena vacation package hotels offer rooms with mountain views, allowing guests to enjoy the island's volcanic landscapes. The 5-star Fairmont Kea Lani Maui, rated 9.2 out of 10 by travelers, is one such property that may include mountain-view room options. Another choice is Castle at Maui Banyan, a 3.5-star property rated 7.9 out of 10 by travelers, which also provides views of the surrounding terrain. The availability of a mountain view depends on the specific room category and package selected.
Are Wailea-Makena vacation package hotels conveniently located?
Wailea-Makena vacation package hotels are generally well-located, often placing you near the area's famous beaches and attractions. Many properties, such as the 5-star Fairmont Kea Lani Maui, rated 9.2 out of 10 by travelers, and the 5-star Wailea Beach Resort - Marriott, Maui, rated 8.7 out of 10 by travelers, are situated directly on or very close to the coastline. This provides convenient access to popular spots like Wailea Beach and Polo Beach, both about 1 mile from central Wailea-Makena, allowing travelers to easily enjoy the scenic views and outdoor activities.
Can I change or cancel my Wailea-Makena vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Wailea-Makena vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Wailea-Makena vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Wailea-Makena vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Wailea-Makena?
To find last-minute vacation packages to Wailea-Makena, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Wailea-Makena vacation packages?
Free cancellation on a Wailea-Makena vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Wailea-Makena vacation as a package or separately?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Wailea-Makena getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Wailea-Makena vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.