Wailea Vacation Packages 2026

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.

Jul 26 - Aug 2
Maui Beach Vacation Club + Flight
North Kihei
7 nights
2.5 star property
8.4/10 - Very Good (881 reviews)
"Beautiful area and lodgings, the lack of AC and the bugs in the kitchen/restroom detracted from the experience."
Reviewed June 4, 2026
Roundtrip • Burbank (BUR) - Maui (OGG)
BUR - OGG • 1 stop OGG - BUR • 1 stop
Save 100% on your flight
~~$1,725~~
$1,117
per traveler
found 23 hours ago
Maui Beach Vacation Club
Aug 5 - Aug 10
Hotel Wailea, Relais & Chateaux - Adults Only + Flight
Wailea
5 nights
5.0 star property
9.4/10 - Exceptional (1,000 reviews)
Roundtrip • Burbank (BUR) - Maui (OGG)
BUR - OGG • 1 stop OGG - BUR • 1 stop
Save 100% on your flight
~~$3,276~~
$1,853
per traveler
found 2 days ago
Hotel Wailea, Relais & Chateaux - Adults Only
Aug 19 - Aug 31
Ho‘olei Villas at Grand Wailea + Flight
Wailea
12 nights
5.0 star property
9.6/10 - Exceptional (47 reviews)
"Overall almost perfect. Some small issues but otherwise would have been a 5/5. Gave it overall a 4 but wish i had a choice for 4.5"
Reviewed May 25, 2026
Roundtrip • Los Angeles (LAX) - Maui (OGG)
LAX - OGG • Nonstop OGG - LAX • Nonstop
Save 100% on your flight
~~$14,863~~
$9,917
per traveler
found 2 days ago
Ho‘olei Villas at Grand Wailea
Aug 8 - Aug 22
Elegant Oceanfront Vistas + Flight
Central Kihei
14 nights
4.5 star property
10/10 - Exceptional (3 reviews)
"Wonderful Place to stay in Kihei. Communicative host. Everything you need for your stay. Great staff and parking. Very clean. Right on the beach, which is fantastic!! As for the Air conditioner; it is not an A/C, its more of an air handler, it does not blow cold air. A bit of a disappointment but everything else made up for that. I would recommend staying here for sure. 4 out of 5 starts jus due to the lack of A/C"
Reviewed March 19, 2026
Roundtrip • Los Angeles (LAX) - Maui (OGG)
LAX - OGG • Nonstop OGG - LAX • Nonstop
Save 100% on your flight
~~$3,108~~
$2,108
per traveler
found 2 days ago
Elegant Oceanfront Vistas
Aug 20 - Aug 26
The Residences at Kamaole Sands Resort + Flight
South Kihei
6 nights
4.5 star property
10/10 - Exceptional (2 reviews)
"The place was very clean. The staff was very communicative and accommodating. I stayed Wednesday-Sunday and I extended my stay 1 night which was very fast and easy. They left us chairs and towels which was very nice for the beach. The place was very spacious for 2 people. If you want to cook this has plenty of counter space. The balcony had a partial ocean view which was very nice. Great value for your money. Check in/out was very easy. You can walk right to the best beaches around. Only Cons..."
Reviewed February 24, 2026
Roundtrip • Los Angeles (LAX) - Maui (OGG)
LAX - OGG • Nonstop OGG - LAX • Nonstop
Save 100% on your flight
~~$1,714~~
$1,169
per traveler
found 1 day ago
The Residences at Kamaole Sands Resort

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.

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 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.

Wailea Hotel Deals

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$945 nightly

$1,122 total

Jun 26 - Jun 27

Total with taxes and fees

9.6/10 Exceptional! (1,001 reviews)

"Absolutely beautiful! Staff were all friendly and attentive. We really appreciated the cleanliness, amenities, and high level of service."

Reviewed on May 25, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$795 nightly

$943 total

Jun 19 - Jun 20

Total with taxes and fees

8.8/10 Excellent! (1,010 reviews)

"The grounds are stunning, the valet staff were amazing! The rooms are about average, the staff working the resort pool and beach were hit or miss. Cleaning staff was kind and thorough as were the staff at the desk at check in. The $55 resort charge, additional taxes and fees added up quickly. The ..."

Reviewed on Jun 4, 2026

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$1,159 nightly

$1,376 total

Jun 16 - Jun 17

Total with taxes and fees

9.4/10 Exceptional! (1,002 reviews)

"The resort was excellent and made for a great trip!"

Reviewed on May 31, 2026

See all 1,226 properties in 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.