Wailea Vacation Packages

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Top Holiday Package Deals in Wailea

Price found within the past 48 hours. Click for updated prices.
The Gardens at West Maui
Napili Kai Beach Resort
Hono Koa Vacation Club
Sands of Kahana
Royal Lahaina Resort & Bungalows

Wailea 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
The price is CA $945 per night from Sep 12 to Sep 13
CA $945
CA $1,204 total
Sep 12 - Sep 13
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Good food great area"

Reviewed on Aug. 10, 2025

Grand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive, Kihei, HI
The price is CA $971 per night from Sep 5 to Sep 6
CA $971
CA $1,146 total
Sep 5 - Sep 6
includes taxes & fees
9.6/10 Exceptional! (999 reviews)
Best hotel ever…
"Everything was top rate! Can’t wait to go back."

Reviewed on Aug. 3, 2025

Four Seasons Resort Maui at Wailea
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
3550 Wailea Alanui Dr, Kihei, HI
The price is CA $1,079 per night from Sep 11 to Sep 12
CA $1,079
CA $1,353 total
Sep 11 - Sep 12
includes taxes & fees
9.2/10 Wonderful! (997 reviews)
"It was ok"

Reviewed on Aug. 3, 2025

Andaz Maui at Wailea Resort - a concept by Hyatt
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.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January72.7°F (22.6°C)No RainMostly SunnySlightly HighAverage
February72.3°F (22.4°C)No RainMostly SunnyAverageSlightly High
March72.7°F (22.6°C)No RainMostly SunnySlightly HighAverage
April74.1°F (23.4°C)No RainMostly SunnySlightly HighAverage
May75.6°F (24.2°C)No RainMostly SunnyAverageAverage
June76.8°F (24.9°C)No RainMostly SunnyAverageAverage
July77.9°F (25.5°C)No RainMostly SunnyAverageSlightly High
August78.4°F (25.8°C)No RainMostly SunnyAverageAverage
September78.4°F (25.8°C)No RainMostly SunnyAverageSlightly Low
October77.7°F (25.4°C)No RainMostly SunnySlightly LowSlightly Low
November75.7°F (24.3°C)No RainMostly SunnySlightly LowSlightly Low
December73.8°F (23.2°C)Light RainMostly SunnySlightly LowSlightly 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.

Frequently asked questions

How much does a Wailea vacation package cost?
The most affordable Wailea package is CA $1,179, 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.

Discover the most popular places to visit in Wailea

Things to do

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