Wailea Vacations

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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.

Price found within the past 48 hours. Click for updated prices.
  • Aug 2 - Aug 7

    Maui Banyan Vacation Club + Flight

    South Kihei
    5 nights
    3.0 star property
    8.0/10 - Very Good (370 reviews)
    "Nice property next to the beach"
    Reviewed May 6, 2026
    Roundtrip Burbank (BUR) - Maui (OGG)
    BUR - OGG1 stop OGG - BUR1 stop
    Save 100% on your flight
    $1,753
    $1,114
    per traveler
    found 16 hours ago
    Maui Banyan Vacation Club
  • Jul 22 - Jul 27

    Hotel Wailea, Relais & Chateaux - Adults Only + Flight

    Wailea
    5 nights
    5.0 star property
    9.4/10 - Exceptional (1,003 reviews)
    "Everything was Amazing!! Will be coming back"
    Reviewed April 18, 2026
    Roundtrip Burbank (BUR) - Maui (OGG)
    BUR - OGG1 stop OGG - BUR1 stop
    Save 100% on your flight
    $4,243
    $2,591
    per traveler
    found 2 days ago
    Hotel Wailea, Relais & Chateaux - Adults Only
  • Jul 1 - Jul 8

    Palms at Wailea Maui + Flight

    Wailea
    7 nights
    3.5 star property
    8.4/10 - Very Good (539 reviews)
    "Twin room had dirty sheets and place was swarmed with mosquitos. "
    Reviewed May 2, 2026
    Roundtrip Burbank (BUR) - Maui (OGG)
    BUR - OGG1 stop OGG - BUR1 stop
    Save 100% on your flight
    $2,936
    $1,861
    per traveler
    found 21 hours ago
    Palms at Wailea Maui
  • Jul 22 - Jul 27

    Hampton Inn & Suites Maui North Shore + Flight

    Kahului
    5 nights
    3.0 star property
    9.2/10 - Wonderful (239 reviews)
    "The staff was very friendly, the rooms were clean with gorgeous views! The connected beach was nice to stroll down as well"
    Reviewed May 12, 2026
    Roundtrip Burbank (BUR) - Maui (OGG)
    BUR - OGG1 stop OGG - BUR1 stop
    Save 100% on your flight
    $1,744
    $1,151
    per traveler
    found 2 days ago
    Hampton Inn & Suites Maui North Shore
  • Aug 5 - Aug 13

    The Ocean View Residence + Flight

    South Kihei
    8 nights
    3.0 star property
    10/10 - Exceptional (1 review)
    "Very nice condo for a longer-term stay. We loved being able to cook. "
    Reviewed October 18, 2025
    Roundtrip Dallas (DFW) - Maui (OGG)
    DFW - OGG1 stop OGG - DAL1 stop
    Save 100% on your flight
    $2,197
    $1,484
    per traveler
    found 1 day ago
    The Ocean View Residence

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.

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

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$903 nightly
The price is $1,072 total per night from May 29 to May 30
$1,072 total
May 29 - May 30
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"The Grand Wailea is more than grand! You will not regret going there, unless you are a constantly angry, miserable soul. Even then, I believe the Grand Wailea can sweep those miseries away. Is it expensive, yes. Is it worth it, absolutely."

Reviewed on May 19, 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
$1,140 nightly
The price is $1,354 total per night from Jun 6 to Jun 7
$1,354 total
Jun 6 - Jun 7
Total with taxes and fees
9.4/10 Exceptional! (1,009 reviews)
"Very happy with our stay and with the staff. All were very friendly."

Reviewed on May 19, 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
$855 nightly
The price is $1,015 total per night from May 26 to May 27
$1,015 total
May 26 - May 27
Total with taxes and fees
9.6/10 Exceptional! (1,000 reviews)
"Great experience"

Reviewed on May 18, 2026

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.

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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.