Wailea Vacation Rentals
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Discover Wailea

The word that comes to mind when thinking of Wailea is “serenity.” Located in South Maui, our Wailea vacation rentals are conveniently near beautiful beaches, breathtaking scenery, delicious cuisine, and so much more. It's the perfect area of Maui for those looking to relax surrounded by the calming ocean breeze. Wailea features 1,500 acres of pristine beach. Five public beach access points form beautiful crescent shapes on the shoreline. We have many different vacation rentals in Wailea to choose from. Reserve your stay today and start packing your sunscreen and sunglasses for a one-of-a-kind getaway.

Did you know that you can save up to 30% off when you book vacation rentals directly with us?

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Beachfront Rentals in Wailea

A beachfront vacation rental in Wailea is the perfect headquarters for you to immerse yourself in the ultimate tropical Hawaiian experience. You’re just steps away from beautiful sandy beaches where you can build sandcastles, search for seashells or just relax in your beach chair during the day, and watch the reflection of the moon shimmer on the ocean water at night.

Wailea Rentals with Pools & Hot Tubs
A Wailea vacation is a perfect way to escape for a little while. Put yourself in time out in one of our vacation rentals with a pool or hot tub. Choose one of our vacation rentals with a pool and enjoy fun in the sun surrounded by beautiful, tropical scenery. Or choose a rental with a hot tub and start or end your day with a refreshing, soothing soak.
Plan Your Wailea Vacation

Miles of gorgeous views, exciting adventures, and a lush landscape will greet you when you arrive for your Wailea vacation. Explore pristine beaches, play a round of golf, catch sight of dolphins and whales, find the perfect souvenir, and try delicious local flavors. The possibilities for exploration and fun are endless and our local office, Maui Rental Group, will share even more ideas with you!

Attractions
Wailea Beaches
Wailea Beaches

Wailea’s shoreline of five nature-made, crescent-shaped beaches and coves offers serenity and privacy amid stunning Pacific Ocean views. Wailea Beach, Polo Beach, and Ulua Beach Park are the most popular beaches in Wailea with abundant opportunities for sunbathing and swimming and water activities like snorkeling and kayaking.

Wailea Golf Club
Wailea Golf Club
Fifty-four holes of championship golf await you at Wailea’s verdant award-winning Blue, Gold, and Emerald courses. Amid a backdrop of jaw-dropping ocean views, Wailea Golf Club offers a variety of fun options whether you are a novice or a seasoned player.
Wailea Oceanfront Boardwalk Trail
Wailea Oceanfront Boardwalk Trail

Perfect for birding or simply strolling along the coast, this partially paved path runs through all five beaches and climbs to Wailea Point, a great spot for whale-watching in the winter and spring months.

Water Sports
Water Sports

Jet skiing, boating, surfing, and paddle boarding are just some of the fun experiences you can enjoy. Snorkeling and scuba diving are considered some of the best in the world at Honolua Bay, Ahihi Kinau Reserve, and Kapalua Bay!

Golfing
Golfing
Breathtaking scenery and one-of-a-kind courses attract golfers from around the world. Explore top golf courses like Kapalua Plantation Course, Wailea Golf Club, Maui Nui Golf Club, Kapalua Golf, and Pukalani Country Club.
Hiking & Biking
Hiking & Biking
There are numerous nature trails in Maui for hikers and bikers of all levels. Go on excursions to see waterfalls, rainforests, volcanoes, and coasts.
The Restaurant at Hotel Wailea
The Restaurant at Hotel Wailea

Voted one of the “Top 10 Best Restaurants in Hawaii,” this award-winning restaurant sources ingredients from local farms and fisheries for fresh, seasonal ingredients. Savor alfresco dining with panoramic views of three Hawaiian Islands.

Monkeypod Kitchen
Monkeypod Kitchen
Widely considered one of the island's best restaurants, Monkeypod serves up fresh, locally caught fish and hand-tossed pizzas featuring seasonal and trending flavor profiles. Enjoy ice-cold brews and delicious meals in a relaxed setting.
Morimoto Maui
Morimoto Maui
Connecting guests to the environment with unrivaled 180-degree views of the beach and ocean, Morimoto Maui invites you to experience dining like you never have before. Featuring traditional and trending Japanese cuisine, the menu’s offerings include hand-rolled sushi and a 10-course Omakase dinner.
Humble Market Kitchin
Humble Market Kitchin
Award-winning Chef Roy Yamaguchi cultivates the sweet and savory flavors of his Hawaiian childhood in a menu that features sumptuous dishes full of vibrant local tastes and global influences from countries like Japan, Portugal, and the Philippines.
The Shops at Wailea
The Shops at Wailea

Shop, dine, and unwind at The Shops at Wailea. Enjoy craft and music lessons, a Polynesian show, and live music amid world-class dining and more than 70 retail and lifestyle stores, including globally known luxury brands and distinctive island artisans.

Wailea Village
Wailea Village
The newest shopping and dining experience, Wailea Village brings a fresh and local perspective to South Maui with shops consisting of locally owned small businesses. Grab a slice at Manoli’s, visit Juvenal Salon for a new look or pick up a new hat at Aloha Hat Company. Make sure to check out the farmer’s market on Tuesday mornings.
Keawala’i Congregational Church
Keawala’i Congregational Church

Experience history at this landmark church. Established in 1832, the church was originally built of pili grass and later reconstructed using lava, timber, and coral mortar. Open to the public, this church invites you to attend a service featuring traditional hula and chants.

Te Au Moana: The Ocean Tide Luau
Te Au Moana: The Ocean Tide Luau
Bringing Polynesian ancestral stories of the ocean to life with traditional song and dance, Te Au Moana will fascinate you with an amazing luau experience. Dine on a three-course Hawaiian feast, dance under the moon and stars of the Maui sky, and discover the history and culture of Hawaii.
Wailea Healing Center
Wailea Healing Center

Wailea’s premier destination for health and wellness, the Wailea Healing Center offers complete wellness of body, mind, and spirit using ancient and modern techniques. Decompress with a traditional acupuncture session or an outdoor Hawaiian-technique massage surrounded by lush Pacific views and the sounds of nature. Enjoy a variety of revolving weekly classes, including free-form dance, mantra singing, and yoga.

Maui Surf Lessons
Maui Surf Lessons
Delight in quality private instructions from passionate professional surfers at Maui Surf Lessons. Detailed instruction and individual attention will have you raising your hand in a Shaka greeting in the spirit of Aloha as you learn to ride the breaking waves of the Pacific. Every lesson comes with free digital photography so you can take your best surfing memories home with you.
Maui Film Festival
Maui Film Festival
Each summer you can experience film premieres, special screenings, and festivities in a solar-powered, open-air festival with panoramic island and ocean views. Over five nights, the Maui Film Festival presents global cinema and transformative storytelling under the stars paired with live music, hula, and festival tributes.
Maui Oceanfront Marathon
Maui Oceanfront Marathon
Dubbed “The Run for Everyone,” the annual Maui Oceanfront Marathon allows for all levels of runners and supports local schools and non-profits in the area. Taking place in January, the run features distances of 5K, 10K, 15K, half-marathon, and marathon along the scenic oceanfront route. Fun Fact: The Maui Oceanfront Marathon is a qualifier for the Boston Marathon. 
Maui Whale Festival
Maui Whale Festival
Held every February for more than 30 years in South Maui, the Maui Whale Festival seeks to commemorate, celebrate, and teach about Humpback Whales.
Guest FAQs
What should I pack for my Wailea vacation?
Sunscreen, bug spray, sunglasses, hat, sandals, swimsuit, cooler, backpack, tennis shoes, weather-appropriate clothes, toiletries, medication, electronics/chargers, rain umbrella.
There is truly no bad time to visit Hawaii! The peak tourist seasons however are the summer months and then the winter season. Surfers have the best conditions during the winter months and many flock to the islands.
We supply you with a limited starter kit of toilet paper, soap, paper towels, and dishwasher detergent for your convenience. There are several shops you can visit nearby to purchase supplies for your stay.
We recommend bringing the following to your Maui rental: trash bags, paper towels, laundry detergent, dishwasher packs, and extra toilet paper.
Save up to 30%

From beachfront condos to houses for large groups, find the best Maui vacation rental for your trip among our wide selection of properties. Plus, you can save up to 30% off your rental just by booking directly with us. Lower fees = more fun!

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Save up to 30%