Wailea Vacations from $725
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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
- Castle at Maui Banyan
Dec 12 - Dec 14Castle at Maui Banyan + Flight
South Kihei2 nights3.5 star property7.8/10 - Good (308 reviews)"Overall we had a wonderful stay as we visited on a family vacation with our 3 children. Staff were very friendly, pool was great, beautiful location! I will say though that the beds were horribly uncomfortable. My husband had to quite literally sleep on the couch cushions placed on the ground as the bed was extremely hard, shook constantly due to any movement. I slept on the bed with our baby and didn’t sleep well the entire week. This is the only issue we had as the matttess topper also was..."Reviewed November 2, 2026Roundtrip • Los Angeles (LAX) - Maui (OGG)LAX - OGG • Nonstop OGG - LAX • Nonstop$1,697$725found 1 day agoper traveler - Hotel Wailea Maui
Jan 6 - Jan 10Hotel Wailea Maui + Flight
Wailea4 nights5.0 star property9.4/10 - Exceptional (1,000 reviews)Roundtrip • Los Angeles (LAX) - Maui (OGG)LAX - OGG • Nonstop OGG - LAX • 2 stops$3,111$1,933found 1 day agoper traveler - Maui Beach Vacation Club
Jan 22 - Jan 25Maui Beach Vacation Club + Flight
North Kihei3 nights2.5 star property8.4/10 - Very good (978 reviews)"It is mainly a time share resort room with kitchen and setting area good for family with kids , no room cleaning , no change towels but you have a washer and dryer. Across the street from small beach , not far from every other needed stores and restaurants, good pool with spa."Reviewed November 4, 2026Roundtrip • Los Angeles (LAX) - Maui (OGG)LAX - OGG • Nonstop OGG - LAX • Nonstop$1,064$728found 1 day agoper traveler - Lahaina Shores Beach Resort By Castle
Jan 22 - Jan 25Lahaina Shores Beach Resort By Castle + Flight
Lahaina3 nights3.5 star property9.4/10 - Exceptional (24 reviews)Roundtrip • Los Angeles (LAX) - Maui (OGG)LAX - OGG • Nonstop OGG - LAX • Nonstop$1,158$798found 1 day agoper traveler - Lumeria Maui Educational Retreat Center
Jan 27 - Jan 31Lumeria Maui Educational Retreat Center + Flight
Makawao4 nights3.5 star property8.6/10 - Excellent (233 reviews)Roundtrip • Los Angeles (LAX) - Maui (OGG)LAX - OGG • Nonstop OGG - LAX • 1 stop
Where to stay in Wailea
South Kihei
While visiting South Kihei, you might make a stop by sights like Kamaole Beach Park 2 and Kamaole Beach Park 3.
Central Kihei
If you're spending some time in Central Kihei, Kihei Regional Park and Kihei Town Center Shopping Center are top sights worth seeing.
North Kihei
If you're spending some time in North Kihei, Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters and Kalepolepo Beach Park are top sights worth seeing.
Makena
A noteworthy feature of Makena is its stunning beaches. While you're in town, be sure to stop and check out Makena State Park Beach and Maluaka Beach.
Halama Street
If you're spending some time in Halama Street, Kihei Town Center Shopping Center and Coast Guard Beach are top sights worth seeing.
Discover the most popular places to visit in Wailea
What to do near Wailea
Akialoa Sunset Sail with Open Bar & Delicious Appetizers from Ma'alaea
Sunset Dinner Cruise aboard Quicksilver: Prime Rib, Fish, Chicken or Pasta
Sunset Dinner Cruise aboard Calypso: Prime Rib, Fish, Chicken or Pasta
Wailea Hotel Deals
"Lovely place."
Grand Wailea Maui, A Waldorf Astoria Resort
Grand Wailea Maui, A Waldorf Astoria Resort
"Nothing"
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Find out more about Wailea
Things to do in and around Wailea
Wailea, Hawaii, offers a perfect blend of beach relaxation and outdoor adventures. Enjoy unforgettable experiences at local golf courses, shop at vibrant malls, or dive into thrilling windsurfing. This scenic paradise is ideal for beach vacations and day trips, with nearby attractions that promise to create lasting memories. Whether you're looking to unwind by the ocean or explore the natural beauty, Wailea has something for everyone.
Shopping
Discover the Shops at Wailea, offering a vibrant mix of entertainment and shopping in a family-friendly atmosphere. For a local touch, visit Kihei Kalama Village, just 3 miles away, or explore the Hali'imaile Farmer's Market, 14 miles distant, for fresh produce and unique finds.
Recreation
The Wailea Gold Golf Course offers a stunning golfing experience surrounded by lush landscapes and ocean views, perfect for sports enthusiasts. For family fun, the Maui Fish Pipe provides exhilarating aquatic activities. The Wailea Blue Golf Course is another great option for outdoor lovers, featuring beautiful fairways and scenic vistas.
Adventure
Embark on the Makamakaole Trail for stunning views, only 4 miles from Wailea. Explore the scenic Kealia Coastal Boardwalk, 8 miles away, perfect for outdoor enthusiasts. For an adrenaline rush, bike down Haleakala with Haleakala Bike Company, located 17 miles away in breathtaking landscapes.
Nightlife
Wailea's nightlife features upscale dining and vibrant bars. Enjoy cocktails at the Monkeypod Kitchen, or unwind at the nearby Andaz Maui's Lehua Lounge for stunning ocean views. For entertainment, check out live music events at the Wailea Beach Resort, offering a perfect blend of relaxation and excitement.
Find the best attractions in and around Wailea
Wailea, Hawaii, is perfect for a beach and outdoor vacation, offering stunning scenery and family-friendly experiences. Explore popular attractions like Wailea Beach and the scenic Wailea Beach Path. Don't miss the nearby resorts and the unique Hawaiian Village for a taste of local culture. Whether you're seeking relaxation on the beach or adventurous outdoor activities, Wailea has something for every traveler.
- Wailea Beach: Experience the stunning beauty of Wailea Beach, known for its soft sands and crystal-clear waters. This beach offers a relaxing atmosphere, perfect for sunbathing, swimming, or taking leisurely strolls along the shore, all while soaking in the tropical vibes of Hawaii.
- Makena State Park Beach: This secluded nudist beach is ideal for couples seeking a romantic escape. Surrounded by lush landscapes and breathtaking ocean views, Makena State Park Beach provides a tranquil setting where you can unwind and connect with nature.
- Kamaole Beach Park 3: Located just 2 miles from Wailea, this urban park is perfect for families. With ample space for picnics, playgrounds for the kids, and easy access to the beach, it offers a lively atmosphere for outdoor fun in the sun.
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.
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.