A beach with clear turquoise water, people sunbathing and swimming, and a mountain in the background.

Wailea Vacation Packages

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The Latest Wailea Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A room with a ceiling fan, a large window with a view of the ocean, a sofa, a table, and a cabinet.
    Jan 29 - Feb 1

    Maui Beach Vacation Club + Flight

    North Kihei
    3 nights
    2.5 star property
    8.4/10 - Very good (986 reviews)
    "It was right across the street from the beach and the ladies at the front desk were amazing. It was a great experience. It doesn’t have a/c but we never needed it at all. It has windows everywhere and it stayed a comfortable temperature in the room the whole stay. It’s an older property but I thought it was kept up very well,theirs an amazing sushi restaurant on site. I would definitely stay here again"
    Reviewed November 13, 2026
    Roundtrip • Edmonton (YEA) - Maui (OGG)
    YEG - OGG • 1 stop OGG - YEG • 1 stop
    CA $1,543
    CA $1,040
    per traveller
    found 1 day ago
    Maui Beach Vacation Club
  • A beach with rocky terrain, palm trees, and a view of the ocean.
    Jan 25 - Jan 30

    The Ocean View Residence + Flight

    South Kihei
    5 nights
    3.0 star property
    9.4/10 - Exceptional (3 reviews)
    "no"
    Reviewed September 28, 2026
    Roundtrip • Edmonton (YEG) - Maui (OGG)
    YEG - OGG • 1 stop OGG - YEG • 1 stop
    CA $3,513
    CA $2,239
    per traveller
    found 1 day ago
    The Ocean View Residence
  • A balcony with a glass table and chairs, overlooking a beach with palm trees and the ocean.
    Jan 29 - Feb 1

    Lahaina Shores Beach Resort By Castle + Flight

    Lahaina
    3 nights
    3.5 star property
    9.4/10 - Exceptional (27 reviews)
    "Love this property! Been coming for the last 30 years"
    Reviewed November 12, 2026
    Roundtrip • Edmonton (YEA) - Maui (OGG)
    YEG - OGG • 1 stop OGG - YEG • 1 stop
    CA $1,766
    CA $1,156
    per traveller
    found 1 day ago
    Lahaina Shores Beach Resort By Castle
  • A staircase leading to a covered area with a view of the sky and clouds.
    Jan 16 - Jan 21

    Hotel Wailea Maui + Flight

    Wailea
    5 nights
    5.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    Roundtrip • Edmonton (YEG) - Maui (OGG)
    YEG - OGG • 2 stops OGG - YEG • 1 stop
    CA $6,028
    CA $4,020
    per traveller
    found 18 hours ago
    Hotel Wailea Maui
  • A hotel room with a large bed, a television, a desk with a chair, a window with a view of palm trees, and a ceiling fan.
    Jan 29 - Feb 1

    Maui Banyan Vacation Club + Flight

    South Kihei
    3 nights
    3.0 star property
    8.0/10 - Very good (406 reviews)
    Roundtrip • Edmonton (YEA) - Maui (OGG)
    YEG - OGG • 1 stop OGG - YEG • 1 stop
    CA $1,695
    CA $1,144
    per traveller
    found 1 day ago
    Maui Banyan Vacation Club

Where to stay in Wailea

Find the best Wailea areas and neighborhoods for the activities you enjoy most. Learn more about Wailea
Learn more about Wailea
A sunset over a beach with palm trees and a few people walking.

South Kihei

While visiting South Kihei, you might make a stop by sights like Kamaole Beach Park 2 and Kamaole Beach Park 3.
A sunset with palm trees silhouetted against a vibrant sky.
Photo by The Camangian's
Open Photo by The Camangian's

Central Kihei

If you're spending some time in Central Kihei, Kihei Regional Park and Kihei Town Center Shopping Center are top sights worth seeing.
A sunset over a calm sea with a distant mountain range and a rocky shoreline.
Photo by Sharen DeGelder
Open Photo by Sharen DeGelder

North Kihei

If you're spending some time in North Kihei, Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters and Kalepolepo Beach Park are top sights worth seeing.
A beach with clear turquoise waters, sandy shores, and lush green hills in the background.

Makena

A noteworthy feature of Makena is its stunning beaches. While you're in town, be sure to stop and check out Makena State Park Beach and Maluaka Beach.

Halama Street

If you're spending some time in Halama Street, Kihei Town Center Shopping Center and Coast Guard Beach are top sights worth seeing.

Discover the most popular places to visit in Wailea

A beach with palm trees, a row of beach umbrellas, and a green boat on the grass.

Wailea Beach

9.4/10 (4,138 reviews)
This stretch of powdery sand is part of an upscale resort community and is an ideal place to sunbathe, snorkel, and dive with Hawaiian green turtles and manta rays.
See properties

What to do near Wailea

Molokini Island

Maui Snorkeling Adventure to Molokini and Turtle Town

CA $226
per adult
90% of travellers recommend
Maui Snorkeling Adventure to Molokini and Turtle Town
See all activities near Wailea

Wailea Hotel Deals

An outdoor lounge area with a thatched roof, fire pit, and multiple seating arrangements.

AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea
4.0 star property
Wailea
9.2 out of 10, Wonderful, (312 reviews)
The price is CA $508
CA $645 total
includes taxes & fees
Nov 22 - Nov 23
AC Hotel by Marriott Maui 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.
See all properties in Wailea

Find out more about Wailea

Things to do in and around Wailea

Wailea, a picturesque destination in Hawaii, is perfect for beach and outdoor enthusiasts. Visitors can enjoy a variety of activities such as golfing at renowned courses, indulging in shopping at local malls, and participating in exciting resort activities. For a unique experience, consider day trips, kayak tours, and the vibrant Te Au Moana Luau, making Wailea an ideal spot for a memorable vacation.

Shopping

For shopping in Wailea, visit Kihei Town Center Shopping Center, 4.8km away, offering a vibrant atmosphere with entertainment and family-friendly options. Whalers Village, 24.8km away, combines shopping and entertainment. Don’t miss One Love Farmers Market, 25.7km away, for local goods and a bustling city vibe.

Recreation

Maui Fish Pipe offers a fun aquatic experience just 4.8km from Wailea, perfect for families. The Wailea Blue Golf Course provides an exhilarating outdoor atmosphere for sports enthusiasts. For ultimate relaxation, Makena Kai Day Spa in Wailea focuses on rejuvenating body treatments in a serene setting.

Adventure

Experience the Makamakaole Trail, a fantastic hiking trail 6.4km from Wailea, offering stunning scenery and outdoor adventure. For a leisurely stroll, head to the Kealia Coastal Boardwalk, located 12.9km away, where you can soak in the beautiful coastal views and enjoy the fresh air.

Nightlife

Wailea boasts a vibrant nightlife with upscale lounges and beachside bars. Enjoy cocktails at the Wailea Beach Resort's pool bar, or dance the night away at the nearby Monkeypod Kitchen, known for its lively atmosphere and local brews. Don't miss the breathtaking sunset views.

Find the best attractions in and around Wailea

Wailea, located in Kihei, Hawaii, is perfect for beach and outdoor vacations, offering stunning scenery and family-friendly experiences. Explore popular attractions like Wailea Beach, Ulua Beach, and the Wailea Resort Community. Don't miss the chance to visit Wailea Gold and enjoy various outdoor activities. Whether you're seeking relaxation or adventure, Wailea has something for every traveller.

  • Wailea Beach: Experience the quintessential Hawaiian beach vibes at Wailea Beach, where soft sands and crystal-clear waters beckon you to unwind. Perfect for sunbathing, swimming, or simply enjoying the stunning sunsets, this beach offers a serene escape amidst lush surroundings.
  • Makena State Park Beach: For a romantic getaway, Makena State Park Beach features picturesque landscapes and a more secluded atmosphere. Known as a nudist beach, it invites you to embrace nature fully, making it an ideal spot for couples seeking privacy and intimacy.
  • Kamaole Beach Park 3: Located two miles from Wailea, Kamaole Beach Park 3 is a vibrant urban park perfect for families. With picnic areas, playgrounds, and a beautiful beach, it offers a delightful mix of outdoor activities and city vibes, ensuring fun for all ages.

Best time to go to Wailea

The best time to visit Wailea can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Wailea falls in August and September. September has average visitor numbers and mostly sunny weather. The coolest average temperature around Wailea falls in February, visitor numbers are average and weather is mostly sunny with no rain.

Tips to save on your trip to Wailea

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Wailea during the low season (September to November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Frequently Asked Questions

How much does a Wailea vacation package cost?

The most affordable Wailea package is CA $1,040, so your dream vacation can become a reality — without it costing a fortune. Combine flights, hotels, car rentals and more to custom build a package that matches your traveling style.

How do I get a cheap travel package to Wailea?

Crafting your own Wailea vacation package with Expedia is the easiest way to save. We have access to more than 550 airlines and 1,000,000 properties across the globe. With such an extensive range to select from, you'll have no trouble pulling together your ideal escape.

Where should I stay in Wailea?

A vacation in Wailea isn't complete without checking out Wailea Beach, Kamaole Beach Park and Makena State Park Beach. Spend your nights close to these top sights and make sightseeing easy.

What are the top hotels in Wailea?

Lock in a room at Ocean And Golf Course View 3 Bed. It's one of this area's most sought-after hotels. Another top-rated option in Wailea is Wailea Ekahi 36b One Of The Best Locations In Wailea.

How far in advance should I book my Wailea vacation?

While prices change from time to time, we generally recommend booking your spot as soon as possible. Most international fares can be compared on Expedia up to a year in advance. If you're booking last minute, you might still be in luck. Discount prices to Wailea occasionally appear in the weeks prior to departure.

What does an Expedia Wailea travel package include?

Car rentals, hotels and flights — we connect you to the very best deals. All you'll have to do is decide on your preferred combination. Once you've made your booking, you can add on the fun stuff like experiences and tours. Our travel packages make it simple to craft an awesome Wailea getaway.

What should I know before booking a Wailea travel package?

You'll pick up amazing savings when you bundle your flights, hotels and rental cars into a package. Plus, booking everything in one spot makes trip planning much easier. So why waste time or money? Whether you're organizing an upscale romantic escape or a budget family adventure, browse our vacation packages today.

If I'm not able to travel, can I cancel my Wailea vacation package?

Yes, you can. We realize life doesn't always go to plan, so we're here to help if you need to make changes to your Wailea vacation package. It may be possible to cancel or change your itinerary for free if you've booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.

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