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.

Luxe
Apartment in Kihei
Wailea Beach Villa PH112
When Paipu Beach and all of the Destination Residences Hawai’i’s luxurious amenities are just steps outside your door, life is easy. Just steps from the beach, this breezy open-concept three-bedroom celebrates Hawaii’s gorgeous natural environment in luxurious fashion. With its wrap-around lanai and unobstructed floor-to-ceiling opening, fresh ocean air and warm natural sunlight fill the penthouse with ease. When it’s time to check out the beach, simply take the elevator downstairs and follow the path, you’ll be there in no time. If you’d like to get out and do some exploring, you’ll find nightlife in Kihei, shopping, and legendary golf at Wailea Blue Golf Course. With a bright and cheerful open-air atmosphere, you’re sure to experience the relaxing Hawaiian way of life at this penthouse. The decor is a mix of plush designer furniture, rich wood textures, eclectic local works of art, and high-end electronics. The kitchen features stained wood cabinetry, granite countertops, and stainless steel appliances that are sure to inspire culinary creativity. And, the balcony is the perfect place to enjoy a relaxing evening. The Wailea penthouse comes equipped with television, Wi-Fi, air conditioning, and a washer/dryer. There’s formal dining space inside for six, and an alfresco set with seating for eight on the balcony. Shared amenities include a swimming pool, fitness center, billiards room, and a shuttle service that transports guests to nearby luxury resorts. If you’d like to visit more of Maui’s beautiful beach area, you won’t have to travel far. There are three more beaches within a ten-minute drive of the Wailea Community. Also nearby, The Shops at Wailea is an open-air mall with over sixty stores by luxury fashion brands, and it’s a great place to have lunch with its many restaurants. If you’ve got a golfer in the group, the Blue Course is a must-play. Blue winds through the resort area and along the coast, offering spectacular ocean views. And, from a few of the holes, you’ll be able to see Mount Haleakala, one of Hawaii’s most picturesque, dormant volcanoes. Copyright © Luxury Retreats. All rights reserved. HAWAII TAX ID #: 016-608-2560-01 BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Dual vanity, Walk-in closet, Television, Air conditioning, Ceiling fan, Safe • Bedroom 2: 2 Twin size beds (can be converted to a king), Ensuite bathroom with combo shower/bathtub combo, Dual vanity, Television, Air conditioning, Ceiling fan • Bedroom 3: Queen size bed, Shared access with hall bathroom with shower/bathtub combo, Television, Air conditioning, Ceiling fan SERVICES INCLUDED • Mid-stay housekeeping - bookings of 6 nights or longer • More under “What this place offers” below SERVICES AT EXTRA COST • Activities & excursions • More under “Add-on services” below SHARED ACCESS TO AMENITIES AT THE DESTINATION RESIDENCES HAWAI'I  Included: • Shuttle service • Swimming pools - oceanfront adult pool & family pool • Fitness center • Billiards room • Small conference center
28 Apr – 5 May
$4,408 SGD per night
5.0 out of 5 average rating, 4 reviews
Luxe
Apartment in Kihei
Makena Surf F208
When Paipu Beach and all of the Destination Residences Hawai’i’s luxurious amenities are just steps outside your door, life is easy. Wake up to spot sea turtles and snorkel boats and end the day with sunsets over the Pacific at Makena Surf F208. This oceanfront Maui vacation rental puts the best of the island at your doorstep, from ocean views and beach access to shopping and golf. Two bedrooms make this villa an ideal choice for a small family, two couples on holiday together or a couple on a dreamy Hawaiian honeymoon. Guests of Makena Surf are welcome to use the shared pool, hot tub and tennis court at Destination Residences Hawaii, as well as the shuttle service between properties. You can also enjoy the balmy temperatures from the villa’s private lanai, which features loungers, a barbecue and an alfresco dining table overlooking the ocean. Huge sliding glass doors give you the luxury of opening the villa’s great room to the lanai for a seamless indoor-outdoor living area. On warmer days, of course, you can shut the doors and relax in the sitting and dining areas in air-conditioned comfort. The great room also includes a fully equipped kitchen with a convenient breakfast bar. The villa’s master bedroom has a king bed and ensuite bathroom, while the second bedroom has a double bed, twin bed and shared access to a hall bathroom. Like the great room, the bedrooms are inviting, island-inspired spaces with neutral tones, traditional furnishings and cheery palm-print artwork and fabrics. Makena Surf F208 is just a 5-minute walk from Paipu Beach, also known as Po’olenalena Beach, a popular spot for everything from romantic sunset strolls to beach wedding ceremonies. By car, it’s 11 minutes or less from three other picturesque sandy beaches, the Wailea Blue Golf Course and, for those in search of souvenirs or a little indulgence or two, the Shops at Wailea. Copyright © Luxury Retreats. All rights reserved. HAWAII TAX ID #:131-05-9056-01 BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower, Dual vanity, Television, Air conditioning, Ceiling fan • Bedroom 2: Double size bed, Twin size bed, Shared access to hall bathroom with shower/bathtub combo, Dual vanity, Television, Air conditioning, Ceiling fan Additional Bedding • Living room: Queen size sofa bed FEATURES & AMENITIES • More under “What this place offers” below STAFF & SERVICES Included: • Shuttle service • More under “What this place offers” below Extra Cost (advance notice may be required): • Activities & excursions • More under “Add-on services” below SHARED ACCESS TO AMENITIES AT THE DESTINATION RESIDENCES HAWAI'I 
22–29 Jun
$2,898 SGD per night
5.0 out of 5 average rating, 3 reviews
Luxe
Villa in Kihei
Anchor Cove D1
Channel your inner surfer at this Maui oceanfront oasis. The soothing sound of gently lapping waves will be the soundtrack to your paradise escape. This laid-back residence instantly channels much-needed relaxation, family-friendly fun, and chill, Hawaiian vibes. Seemingly endless stretches of powdery sand and crystal clear, cerulean waters are a mere 20 steps from your private, backyard lanai. Modern design merges with traditional details and warm, rich décor in the sprawling, open-concept space. Enormous 40-foot sliding doors open up from the main living area onto the vast terrace. There’s no denying that the evening starts at the wine bar; pre-dinner Mai Tais will quickly become your daily routine. Playing the role of gourmet chef is easy-breezy in the spacious kitchen, with options to dine both inside and alfresco. Pop open a bottle of crisp champagne as you watch the mesmerizing sunset ignite the sky with a mélange of tangerine hues. Only 100ft away from snorkelling, get ready for a glimpse of the vibrant marine life - think turtles - that thrives under the ocean. Looking for a lively night? Button up your botanical-printed aloha shirt and head out on the town. Retreat to the sumptuous sofas after a day of adventure—either with a view of the garden or with the electronic shades drawn and the fireplace flickering. With noise reduction windows in the bedrooms, you’re guaranteed to fall fast asleep as soon as your head hits the pillow.  Registration Permit TA-164-629-2992-01 Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Television, Safe, Office space, Air conditioning, Ocean view • Bedroom 2: Queen size bed, Access to hallway bathroom shared with Bedroom 3, Stand-alone shower, Television, Air conditioning • Bedroom 3: Queen size bed, Twin size Murphy bunk bed, Access to hallway bathroom shared with Bedroom 2, Stand-alone shower, Television, Safe, Air conditioning FEATURES & AMENITIES • More under “What this place offers” below OUTDOOR FEATURES • Lanai Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below Included: • More under “What this place offers” below
7–14 Dec
$3,060 SGD per night
5.0 out of 5 average rating, 7 reviews

Popular amenities for Wailea, Wailea-Makena luxury holiday rentals

Other great luxury holiday rentals in Wailea, Wailea-Makena

Luxe
Villa in Kihei
Wailea Beach Villa PH205
12–19 Jul
$4,408 SGD per night
5.0 out of 5 average rating, 3 reviews
Luxe
Villa in Kihei
Wailea Beach Residence B101
28 May – 4 Jun
$6,683 SGD per night
5.0 out of 5 average rating, 4 reviews
Luxe
Apartment in Kihei
Wailea Beach Villa PH411
14–21 Aug
$4,265 SGD per night
New place to stay
Luxe
Apartment in Kihei
Wailea Beach Villa PH512
1–8 Nov
$4,479 SGD per night
New place to stay
Luxe
Villa in Makena
Makena Surf E103
14–21 Sep
$2,898 SGD per night
New place to stay
Luxe
Apartment in Kihei
Wailea Beach Villa PH502
10–17 Jun
$4,265 SGD per night
New place to stay
Luxe
Apartment in Kihei
Wailea Beach G302
17–24 May
$6,257 SGD per night
New place to stay
Luxe
Villa in Kihei
Wailea Beach Villa PH301
11–18 Aug
$4,977 SGD per night
New place to stay
Luxe
Apartment in Kihei
Wailea Beach Villa PH306
17–24 Nov
$4,265 SGD per night
New place to stay
Luxe
Apartment in Kihei
Wailea Beach Villa PH410
19–26 Oct
$4,265 SGD per night
New place to stay
Luxe
Apartment in Kihei
Wailea Beach Villa PH504
15–22 Jul
$4,265 SGD per night
New place to stay
Luxe
Apartment in Kihei
Wailea Beach E201
22–29 Oct
$5,830 SGD per night
New place to stay

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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Hawaii
  4. Maui County
  5. Wailea-Makena
  6. Wailea
  7. Luxury rentals