Wailea Vacation Rentals

Discover Wailea, Maui’s ultimate coastal escape. This luxurious, 1,500-acre resort community boasts pristine crescent beaches, high-end resorts, and premier ocean activities, from snorkeling to paddleboarding. Visitors can explore the scenic Wailea Boardwalk, indulge in upscale shopping at The Shops at Wailea, and savor local flavors at renowned eateries. With year-round sun, championship golf courses, and stunning views of Molokini Crater, Wailea is the perfect blend of relaxation and adventure.

A luxurious resort community spanning over 1,500 acres of Maui's southwestern coast, Wailea is home to some of the most exclusive resorts, spas, golf courses, shopping, and dining the island has to offer. With Kihei at its north and Makena to the south, the upscale beach town sits at the center of all South Maui activity. Average temperatures ranging from 72 to 84 degrees and the least annual rain on the island make this area ideal for year-round beach days and time spent playing in the ocean. While mornings welcome gentle breezes and glassy ocean conditions, trade winds tend to blow strong cooling gusts in the afternoon heat.  

Its five pristine crescent-shaped beaches offer soft sands and calm waters, perfect for ocean activities like snorkeling, paddle boarding, kayaking, surfing lessons, and more. The largest and most recognized of its beaches, Wailea Beach, is fronted by 5-star resorts, including the Grand Wailea and Wailea Four Seasons, as well as luxury rental villages like Wailea Beach Villas. Intimate and private, Wailea exudes a relaxed, often quiet atmosphere compared to other, more crowded areas of the island. 

Spend your days exploring the three miles of stunningly manicured Wailea Boardwalk that hug the coast and soak in views of the turquoise Pacific Ocean, contrasted beautifully by lush, colorful foliage and jagged cliffs carved from lava rock. The gorgeous path conveniently connects each resort to the next, making it easy to access the fine dining, high-end spas, and other lavish amenities they offer. Meaning "Waters of Lea," Wailea is named after the Hawaiian goddess of canoe makers who was said to have transformed into a bird and flown over this very shoreline.

Golfers will enjoy stunning panoramic mountain and ocean views from Wailea's three challenging hillside courses, including the Blue Course, Emerald Course, and Gold Course, as well as a nearby seaside course located to the south in Makena. Wailea's Blue Course delivers wide fairways and stunning ocean views, while the lush, manicured landscaping makes the Emerald Course an enjoyable experience. Known for its challenging natural hazards, doglegs, and narrower fairways, the prestigious Gold Course has even been host to the Senior Skins game televised nationally on Super Bowl Sunday. 

Conveniently located in the heart of Wailea, surrounded by the top resorts in the area, the Shops at Wailea is an open-air outdoor mall boasting some of the best shopping and dining on the island. Home to more than 70 boutiques, shops, restaurants, and galleries, it is Maui's premier shopping destination and the only center to offer luxury brands like Gucci, Louis Vuitton, Bottega Veneta, Coach, and more. The shops also offer daily entertainment and events ranging from coconut husking demonstrations and live music to Polynesian dance performances.

Wailea is also host to events such as the Maui Film Festival, February’s Whale Week, and award-winning restaurants serving the best of Hawaii’s cuisine. From fine dining to casual cafes, this area has it all. Indulge in exceptional upscale dining choices with breathtaking ocean views and modern poolside seating at Wailea resorts like the Four Seasons, Fairmont Kea Lani Maui, Wailea Beach Mariott, and Grand Wailea. Venture north to Kihei and explore delicious smaller eateries, lively bars, food trucks, and shave ice stands. 

To the south, Makena is a small serene community occupying a stretch of terrain that reaches as far south as one can go by car before the road ends. Adventurous travelers will enjoy the numerous hikes along lava beds that formed in this area two centuries ago after Haleakala's last eruption, including the King's Highways and La Perouse Bay. But perhaps the most popular of its attractions is Makena Beach State Park, one of the largest and most breathtaking beaches on Maui. Prior to the 1980s when resort infrastructure began, this area of the island was only accessible by 4-wheel drive vehicles and continues today to feel like slightly untouched terrain compared to other areas of the island. Nestled between two clusters of black-lava rock, the beach offers protection from the trade winds and provides great views of Molokini Crater and Maui's neighbor island Kahoʻolawe.

Bursting with lively volcanic reefs full of brightly colored coral and beautiful tropical fish, snorkelers and deep-sea adventurers can observe spectacular marine life right off nearly all of Wailea’s beaches. Arguably Maui's most popular excursion and one of the best locations to experience the underwater world, though, is by booking a snorkel tour of Molokini Crater. Nearly half a mile wide and reaching 160 feet above sea level, the crescent-shaped crater that sits just off Wailea's shores is Hawaii's only island marine sanctuary. Its crystal clear water and abundant marine life make it a premier snorkeling destination. Those staying in Wailea have the advantage of being just five minutes from a snorkel catamaran that leaves Maluaka Beach in Makena daily. 

At sunset, Wailea travelers will have a front-row seat to the vibrant torch-lit pathways and changing pastel hues that fill the landscape. Drums and live music can be heard nightly from luxury Luaus at the Andaz, Grand Wailea, and Marriott Wailea Beach Resort. Each offers a uniquely curated cultural and culinary experience set against stunning views of the Pacific Ocean. 

Although our Wailea accommodations offer everything you will need for a terrific Hawaiian vacation, many of the incredible shops, restaurants, beaches, and activities are within a short drive. Should you choose to venture to other parts of the island, like Haleakala National Park or want to travel the road to Hana, we recommend booking a rental vehicle or tour to reach these areas. 

Experience the space and comfort of home coupled with the luxurious services and high-end amenities of resort living in a Wailea vacation rental. Browse our full selection of Wailea vacation rental listings below to find out which destination is best for your travel needs, and please do not hesitate to contact one of our Reservation Liaisons with any questions you may have.

Wailea Highlights

• An exclusive resort community located in the heart of South Maui.
• Year-round warm sunny weather with average temperatures ranging from 72-85 degrees. 
• A short 25 minute drive from Kahului Airport. 
• Five pristine crescent shaped beaches, including the world-famous Wailea Beach. 
• Three championship golf courses, with a nearby seaside course located five minutes south in Makena. 
• Home to the upscale Shops at Wailea, an open-air luxury outdoor shopping and dining center.