Skip to content

Luxury rentals in Wailea, Wailea-Makena

Find and book unique accommodation on Airbnb

Top-rated luxury holiday rentals in Wailea, Wailea-Makena

Guests agree: these stays are highly rated for location, cleanliness, and more.

Wailea Beach Villa PH211
Entire villa · 6 guests · 3 beds · 2 baths
Wailea Beach Villa PH211
Wailea Beach Residence B101
Entire villa · 6 guests · 3 beds · 3.5 baths
Wailea Beach Residence B101
Wailea Beach Villa PH112
Entire condominium (condo) · 6 guests · 4 beds · 3 baths
Wailea Beach Villa PH112

Luxury rentals for every style

The right home for your next dream getaway

  • Featured Homes
  • Flexible bookings
  • Ready to book homes

Popular amenities for Wailea, Wailea-Makena luxury holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Air conditioning

Other great luxury holiday rentals in Wailea, Wailea-Makena

LUXEEntire villaRating 5 out of 5; 3 reviews
Wailea Beach Villa PH205
$3,891 / night
LUXEEntire condominium (condo)
Wailea Beach Villa PH411
$3,741 / night
LUXEEntire condominium (condo)
Wailea Beach G302
$5,837 / night
LUXEEntire villa
Wailea Beach Villa PH301
$2,918 / night
LUXEEntire condominium (condo)
Wailea Beach Villa PH504
$3,741 / night
LUXEEntire condominium (condo)
Wailea Beach Villa PH410
$3,741 / night
LUXEEntire condominium (condo)
Wailea Beach Residence E202
$4,490 / night
LUXEEntire condominium (condo)
Wailea Beach Villa PH512
$5,388 / night
LUXEEntire condominium (condo)
Wailea Beach Villa PH502
$3,741 / night
LUXEEntire villa
Wailea Beach C102
$3,711 / night
LUXEEntire condominium (condo)
Wailea Beach Villa PH302
$3,741 / night
LUXEEntire condominium (condo)
Wailea Beach Villa PH306
$3,741 / night

All about Wailea, Wailea-Makena

Planning a vacation in Wailea? We’re here to help!

On the island of Maui, Wailea boasts many acres of sun-kissed golden beaches fringed with lush palm trees. There’s great golfing, restaurants and high-end resorts galore. It’s also easy to get to – just 30 minutes from Kahului Airport, the island’s primary travel hub. Direct flights land here daily from cities including L.A. Las Vegas, San Francisco, Chicago, and more, while one-stop connections can be found from many others.

Maui is a year-round destination, with good weather and warm days at any point in the year. You’ll find the island is at its busiest during the summer months (June-August) and over the winter months, from mid-December to mid-April. A thriving island with a local population of some 150,000 people, attractions, and restaurants are open all year.  

Miles upon miles of beaches

Hawaii is famous for its many beaches, which range from white and golden sands to black, and even green sand! In Wailea, the beaches are blonde and beautiful, lapped by the Pacific Ocean and backed by swaying palms.

Wailea Beach, which has been named “America’s Best Beach” in years past offers a wide expanse of golden sand. The main beach in the area, it is home to several resorts including the Grand Wailea and the Four Seasons, so you’ll be sharing the beach here with parasols and loungers, but you’ll alose have access to plenty of amenities, including beach bars and restaurants.

Slightly further afield, some 5 miles down the road, is Makena Beach, one of the island’s best-loved stretches of sand. For bodyboarding or just simply taking some sun, it’s hard to beat. There’s a lifeguard on duty and basic amenities but none of the resort scene you’ll find at Wailea Beach. If you want to swim, head down to Little Beach at the western end, but be aware, it’s a clothing optional area.

Golf courses galore

For many people, a trip to Maui is not complete without a few rounds of golf, and Wailea is home to some of the island’s top courses. The area has three championship courses – the Wailea Emerald, Wailea Blue and Wailea Gold, which each offer a different experience.

With spectacular ocean views, the Emerald course is a bucket-list item for many golfers, and it has won awards from Golf for Women magazine for being one of the country’s most women-friendly golf courses.

The Gold course has numerous tee boxes for every hole, making it eminently playable for golfers of all abilities. It was designed by the legendary Robert Trent Jones II and has been referred to as the “thinking player’s course” due to its many challenging aspects.

The Blue course was the club’s original course, and it still has a whole lot to offer. Designed by Arthur Jack Snyder the venerable course is nicknamed the “Grand Lady of Wailea.” With views over the towering Haleakala volcano and the Pacific Ocean, it can be a challenge to keep your mind on your game here.

Seriously good spas

If golf doesn’t figure in your idea of a good time, how about some seriously indulgent spa treatments? Where sleek resorts set food, world-class spa options follow, and Wailea is no exception. Our favorites include the spa at the Fairmont Kea Lani (where Luxury Retreats also has luxurious apartments) and spa at the Four Seasons.

The award-winning Willow-Stream Spa at the Fairmont resort offers state of the art treatments designed to relax and revitalize visitors, including a facial that uses NASA-developed technology to tighten skin and reduce sun spots. Of course, you’ll also find massages, pools, rain showers, steam rooms, and saunas here.

At the Four Seasons, you can try the HydraFacial, which uses a water-based dermabrasion system to renew the surface of the skin. If you do try the treatment, you might see a beaker full of grubby water at the end, and yes, that’s all the residual dirt and impurities that have been removed from your skin! The surroundings here are chic and calm with an infinity pool overlooking the ocean.

For an indulgent afternoon, the spa at the Grand Wailea offers 50,000 sq ft dedicated to refreshing body and mind. Its spa treatments are based on traditional Hawaiian rituals. Sign up for the Termé Wailea Hydrotherapy Circuit and feel your worries melt away as you move from pool to pool, with loofah scrubs and waterfalls thrown in.

Experience the luxury of our Wailea vacation rentals

Whether you’re looking for a secluded spot or an oceanfront rental with resort amenities as standard, you’ll find all these options and more in Wailea.

Beachfront villas

Our Wailea beach villas all have a few things in common: gorgeous ocean views, terraces where you can enjoy a sunset snack, and comfortable beds for you to rest your head at the end of a busy day. Sleeping up to 6 people, whether you’re traveling with friends, or family there’s room for everyone. Amenities like kids clubs and shared access to spacious lagoon pools makes these homes a great option if you’re planning a vacation with your children.


Honeymoon in Wailea

Maui is a popular destination wedding spot for good reason – it’s also a great place to enjoy a post-wedding vacation. If you’re planning a Wailea honeymoon , Luxury Retreats has a host of good options. Our one- and two-bedroom suites and bungalows put you in the heart of the action – whether that means chilling by the pool, treating yourself at the spa, playing a round of golf together, or hiring a car and exploring further afield. Rest assured, when the day is done and you’re heading home, you’ll have a wealth of dining options right on your doorstep.