How much does a Wailea vacation package cost?

The most affordable Wailea package is CA $2,063, 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.

Wailea Vacation Packages & Trips 2026 from CA $2,063

Top Holiday Package Deals in Wailea

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

Kahana Beach Vacation Club

CA $2,063

per person

Apr 2 - Apr 9

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Kahului (OGG)

8.4/10 Very Good! (744 reviews)

The view 😍🌅🐢🐳 incredible is right. We were originally in a partial ocean view (701), it was windy the week we were there, the first night was awful, I thought the sliding glass door was going to shatter and/or the building was going to blow away. I asked to be moved to a lower floor due to the wind, the gal at the front desk was nice and said she could get us a front facing view the next day so we took it. The second night in 701 was not building-blow-away bad but it was still windy, once we moved to the front facing, it took our vacation from good to epic. Oh that view, you literally felt like you were above the water. We watched so many whales jump from our balcony and a few turtles come hang on the beach. The beach was small and always wet but still a great little beach there. Both rooms were clean, the grounds are nothing to speak of but well maintained, the hot tub was a warm tub however they were working on it while we were there and on our last night the Jets were on, the pool was not heated and colder than the ocean. They have great sun loungers that were perfect for relaxing and whale watching. Oh and the BBQ's were great too and a fun hang out/meet other people area while making dinner. All in all it was a great stay for a budget place, I would stay here again. If you are looking for more amenities and nicer grounds with plants, ponds, restaurants and more this wouldn't be your place but if you want a right on the water experience, stay here!

Reviewed on Feb 25, 2026

Sands of Kahana

CA $2,192

per person

Apr 12 - Apr 19

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Kahului (OGG)

8.2/10 Very Good! (453 reviews)

The room was great!! Super spacious, comfortable, and affordable. The staff were nice as well.

Reviewed on Feb 19, 2026

Kahana Villa

CA $2,229

per person

Apr 12 - Apr 19

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Kahului (OGG)

8/10 Very Good! (351 reviews)

Clean, spacious, friendly staff, and amenities

Reviewed on Feb 24, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

CA $4,697

per person

May 3 - May 10

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Kahului (OGG)

9.4/10 Exceptional! (1,001 reviews)

Everything was exceptional! Great property, quiet and peaceful

Reviewed on Jan 6, 2026

Maui Beach Vacation Club

North Kihei

CA $2,226

per person

Apr 8 - Apr 15

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Kahului (OGG)

8.2/10 Very Good! (814 reviews)

Room was sticky had to wipe things down . Shower leaked through the wall and soaked the carpet in the next room. The dish washer was not secured so it tiped over when ever it was opened . The washer and dryer were not level so the load was out of balance andnthe door would not stay open to load the dryer.

Reviewed on Feb 18, 2026

Things to do in and around Wailea

Wailea offers a perfect escape for beach lovers and outdoor enthusiasts alike. Visitors can enjoy a variety of activities, including world-class golf at nearby courses, shopping at local malls, and exciting resort activities. Don't miss the opportunity for a memorable day trip, kayak tours, or the lively Te Au Moana Luau, showcasing Hawaiian culture. Whether you're seeking relaxation or adventure, Wailea has something for everyone.

Shopping

The Shops at Wailea offers a vibrant shopping experience with a mix of entertainment and family-friendly vibes. For a local touch, visit Kihei Kalama Village, just 4.8km away, or explore the Hali'imaile Farmer's Market, located 22.5km from Wailea, for unique souvenirs and treats.

Recreation

At Wailea Gold Golf Course, enjoy a challenging round of golf amidst breathtaking landscapes, perfect for outdoor enthusiasts. For family fun, visit Maui Fish Pipe, an exciting aquatic centre offering thrilling water activities. Lastly, indulge in rejuvenating treatments at Makena Kai Day Spa, where relaxation and wellness await.

Adventure

The Makamakaole Trail, located 6.4km from Wailea, offers breathtaking scenery and an exhilarating hiking experience. For a leisurely stroll with stunning coastal views, explore the Kealia Coastal Boardwalk, situated 12.9km away. Science City, an arcade adventure zone 19.3km from Wailea, is perfect for family fun and excitement.

Nightlife

Wailea’s nightlife offers a blend of elegance and relaxation. Enjoy a cocktail at the upscale Monkeypod Kitchen or unwind with live music at the charming Mulligan's on the Blue. For a more laid-back vibe, visit The Shops at Wailea for boutique bars and casual dining options.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Wailea

Wailea, located on the beautiful island of Maui, is perfect for beach and outdoor enthusiasts seeking stunning scenery. Visitors can explore popular attractions like Wailea Beach, Ulua Beach, and the Wailea Gold golf course. The area also features a welcoming resort community, making it an ideal destination for families looking to enjoy the sun and surf. Whether you're lounging on the beach or discovering the Hawaiian Islands, Wailea promises a memorable vacation experience.

Wailea Beach: Wailea Beach is a stunning, picturesque beach that embodies the quintessential Hawaiian experience. With soft golden sands and crystal-clear waters, it offers a perfect spot for sunbathing, swimming, and enjoying breathtaking sunsets. The relaxed beach vibes create an inviting atmosphere for visitors to unwind and soak in the natural beauty of the area.
Makena State Park Beach: Renowned for its romantic vibes, Makena State Park Beach is a beautiful nudist beach that provides a sense of freedom and tranquility. Surrounded by lush landscapes and pristine waters, this beach is an ideal getaway for couples seeking intimacy and connection with nature.
Kamaole Beach Park 3: Located 3.2km away from Wailea, Kamaole Beach Park 3 is a vibrant urban park perfect for families. With picnic areas, grassy spaces, and easy beach access, it offers a fun, outdoor atmosphere for children and adults alike to enjoy various activities and beach games.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	72.7°F (22.6°C)	No Rain	Mostly Sunny	Slightly High	Average
February	72.3°F (22.4°C)	No Rain	Mostly Sunny	Average	Slightly High
March	72.7°F (22.6°C)	No Rain	Mostly Sunny	Slightly High	Average
April	74.1°F (23.4°C)	No Rain	Mostly Sunny	Slightly High	Average
May	75.6°F (24.2°C)	No Rain	Mostly Sunny	Average	Average
June	76.8°F (24.9°C)	No Rain	Mostly Sunny	Average	Average
July	77.9°F (25.5°C)	No Rain	Mostly Sunny	Average	Slightly High
August	78.4°F (25.8°C)	No Rain	Mostly Sunny	Average	Average
September	78.4°F (25.8°C)	No Rain	Mostly Sunny	Average	Slightly Low
October	77.7°F (25.4°C)	No Rain	Mostly Sunny	Slightly Low	Slightly Low
November	75.7°F (24.3°C)	No Rain	Mostly Sunny	Slightly Low	Slightly Low
December	73.8°F (23.2°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly High

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.

Where to stay in Wailea

Find the best Wailea areas and neighborhoods for the activities you enjoy most. Learn more about Wailea

Wailea Hotel Deals

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

CA $904

CA $1,162 total

Mar 11 - Mar 12

includes taxes & fees

8.8/10 Excellent! (1,007 reviews)

Everything was great especially the grounds absolutely stunning. The only knock i would give it is the outside of the overall hotel needs a bit of paint or some refreshment other than that the rooms were spacious clean and the grounds were gorgeous kids loved the pool and beach very much overall ...

Reviewed on Feb 25, 2026

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

CA $1,226

CA $1,545 total

Mar 21 - Mar 22

includes taxes & fees

9.6/10 Exceptional! (1,000 reviews)

Everything about this hotel is incredible!

Reviewed on Feb 20, 2026

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr Kihei HI

CA $1,057

CA $1,351 total

Mar 8 - Mar 9

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

nice room and location. Love everything here - especially the early yoga/meditation class we took under the big tree.

Reviewed on Feb 17, 2026

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.