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Your Wailea Vacation

Lose yourself in the magic of this picturesque neighborhood with a Wailea vacation package. From its surfing and coastal beaches to its views, there's something here for every traveler. Not sure what to do and see during your trip to Wailea? Nearby attractions such as Wailea Beach, Kamaole Beach Park and Keawakapu Beach North are good places to start. Whatever your travel plans or budget, booking your dream Wailea vacation is quick and easy with Expedia.

The Latest Wailea Vacation Packages

Price found within the past 48 hours. Click for updated prices.
AEI at Kaanapali Shores
Hyatt Vacation Club at Ka'anapali Beach, Maui
Maui Banyan Vacation Club
Mana Kai Maui- Official Onsite Rental
Kahana Beach Vacation Club

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
$758 nightly
The price is $894 total per night from Aug 19 to Aug 20
$894 total
Aug 19 - Aug 20
Total includes taxes and fees
8.8/10 Excellent! (1,003 reviews)
"The rooms were comfortable. Shower was great! Kids loved the giant bathtub! Pools were nice. Tarzan swing was fun. Staff was friendly"

Reviewed on Aug 2, 2025

Grand Wailea Maui, A Waldorf Astoria Resort
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
$767 nightly
The price is $904 total per night from Aug 12 to Aug 13
$904 total
Aug 12 - Aug 13
Total includes taxes and fees
9.2/10 Wonderful! (997 reviews)
"I loved everything about the property The ocean view was most beautiful. I can’t wait to return!"

Reviewed on Jul 12, 2025

Andaz Maui at Wailea Resort - a concept by Hyatt
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
$857 nightly
The price is $1,011 total per night from Aug 11 to Aug 12
$1,011 total
Aug 11 - Aug 12
Total includes taxes and fees
9.4/10 Exceptional! (999 reviews)
"Great"

Reviewed on Aug 1, 2025

Fairmont Kea Lani Maui
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 is perfect for a beach vacation, offering stunning scenery and outdoor activities. Enjoy world-class golf courses, explore local shopping centers, and embark on unforgettable day trips. Don't miss nearby attractions and thrilling windsurfing experiences that promise lasting memories. Whether you're relaxing on the beach or seeking adventure, Wailea has something for everyone.

Shopping

In Wailea, visit the Shops at Wailea for a delightful shopping experience with a mix of entertainment and family-friendly vibes. Just 3 miles away, Kihei Kalama Village offers a vibrant atmosphere, while the Haliimaile Farmer's Market, located 14 miles from Wailea, provides a taste of local culture and goods.

Recreation

Experience the Wailea Gold Golf Course, where you can enjoy a round of golf surrounded by stunning landscapes. For relaxation, visit Makena Kai Day Spa, offering rejuvenating body treatments in a tranquil setting. Don’t miss the Maui Fish Pipe for some fun aquatic activities perfect for families.

Adventure

The Makamakaole Trail, located 4 miles from Wailea, offers a thrilling hike with breathtaking scenery. Enjoy the Kealia Coastal Boardwalk, 8 miles away, for a scenic stroll with coastal views. For family fun, visit Science City, 12 miles from Wailea, featuring exciting arcade adventures for all ages.

Nightlife

Wailea's nightlife offers a blend of upscale lounges and vibrant bars. Enjoy cocktails at the elegant Monkeypod Kitchen or unwind with a sunset view at the Four Seasons Resort. For a lively atmosphere, visit the nearby Kihei, where beach bars and live music thrive.

*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 is perfect for a beach and outdoor vacation, offering stunning scenery and a variety of attractions. Explore Wailea Beach and Ulua Beach for warm Hawaiian waters, or enjoy the local resorts and the unique Hawaiian village. Whether you're seeking family-friendly experiences or a relaxing day at a nudist beach, Wailea has something for everyone, making it an ideal destination for your getaway.

  • Wailea Beach: Experience the stunning beauty of Wailea Beach, known for its soft sands and vibrant beach vibes. It's a perfect spot for sunbathing, swimming, and enjoying breathtaking sunsets over the Pacific.
  • Makena State Park Beach: Embrace the romantic atmosphere of Makena State Park Beach, a unique nudist beach that offers a secluded and serene environment, ideal for couples looking to connect and unwind in nature.
  • Kamaole Beach Park 3: Just 2 miles from Wailea, Kamaole Beach Park 3 is a family-friendly urban park featuring picnic areas, lifeguards, and gentle waves, making it perfect for a fun-filled day outdoors with loved ones.

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 during the off-peak season (typically September to November) for more affordable package holidays to Wailea.
  • 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.

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.