Luxury rentals in Wailea, Wailea-Makena

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

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Villa in Kihei

5.0 out of 5 average rating, 3 reviews

Wailea Beach Villa PH205

When Paipu Beach and all of the Destination Residences Hawai’i’s luxurious amenities are just steps outside your door, life is easy. Situated within the Wailea Beach Resort, this bright and cheerful three-bedroom apartment is the perfect home base for an unforgettable Hawaiian, family vacation. Just steps away, you’ll have access to one of Maui’s most prestigious beachfront, Wailea Beach. Its rocky borders are great for snorkeling, boogie boarding, and body surfing. Along the center of the beach, the water is much more calm, ideal for children and casual swimmers. Nearby in Kihei, you’ll love the vibrant tourism atmosphere featuring golf, dining, activities and excursion packages, and a wide range of shopping. An open concept floor plan and high-end designer furniture make this penthouse a social space for family fun. You’ll love the eclectic art, and vibrant Hawaiian decor found throughout. In the kitchen, stainless steel appliances and functional granite countertops create an exciting working environment. And, a wide opening to the balcony ensures fresh breeze and natural sunlight flow to freely through the apartment. Wailea’s beach penthouse has formal dining with space for six, and there’s an alfresco set with seating for four on the balcony, along with a barbecue. While you’re exploring the resort’s estate, visit their swimming pools, hot tubs, fitness center, billiards room, and beachfront, to which you’ll have shared access. There’s plenty to see and do in nearby town, Kihei. Known for its exciting outdoor environment, it’s always easy to find a beachfront restaurant, cocktail bar, or secluded spot to watch the sunset. 5 Palms is one of Kihei’s best cocktail bars, just steps from the beach, it is quite popular around sunset, so it’s a good idea to arrive a little before. If you’d prefer locally crafted beer, the Maui Brewing Co is always a great place to stop in and see whats new on tap. There are also lots of great restaurants and retail outlets at the open-air mall, The Shops at Wailea. And, if there’s a golfer in the group, Wailea Blue is one of the best courses in Hawaii. With challenging fairways that weave through the resort and scenic ocean and volcano views, Blue is a must-play for any golf aficionado. Copyright © Luxury Retreats. All rights reserved. HAWAII TAX ID #: 162-093-0560-01 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, Direct access to balcony • Bedroom 2: Queen size bed, Shared access with hall bathroom with shower/bathtub combo, Dual vanity, Television, Air conditioning, Ceiling fan • Bedroom 3: 2 Twin size beds, Ensuite bathroom with shower/bathtub combo, Television, Air conditioning, Ceiling fan STAFF & SERVICES Extra Cost (advance notice may be required): • Activities & excursions SHARED ACCESS TO AMENITIES AT THE DESTINATION RESIDENCES HAWAI'I  Included: • Swimming pools - oceanfront adult pool & family pool • Hot tub • Fitness center • Billiards room • Shuttle service • Conference center

Sep 8 – 15

$3,277 per night

Condo in Kihei

5.0 out of 5 average rating, 4 reviews

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

Aug 16 – 23

$2,949 per night

Condo in Kihei

Wailea Beach Villa PH411

When Paipu Beach and all of the Destination Residences Hawai’i’s luxurious amenities are just steps outside your door, life is easy. This Wailea beach penthouse is perfect for a couples retreat, small family vacation, or romantic honeymoon. With two-bedrooms, walking access to the beach, and plenty of amenities within the Destination Residences Hawai’i estate, you’ll have everything you need for an amazing vacation, just steps away. The penthouse balcony features a spectacular ocean view, great for catching Maui’s amazing sunsets, starry skies, and even whale watching. Nearby, the city of Kihei is full of romantic dining options, beachfront bars, and the most vibrant nightlife scene on the island. The ocean-view living room of Wailea’s penthouse is decorated in a way that combines elegance, excitement, and tradition all into one welcoming space. With earthy tones, warm wood, and floral print, Hawaii’s gorgeous nature is well represented. Designer furniture, high-end appliances and fixtures, and intricate works of art add a touch of modern luxury and class to the interior. And, bright splashes of color, wide openings to the balcony, and spectacular ocean views add a burst of energy to the penthouse ambiance. While you’re enjoying your stay at the Wailea Beach Residence, make sure to check out some of their luxurious shared amenities, like swimming pools, hot tubs, billiards room, a fitness center, and a shuttle service that will transport guests between neighboring resorts. At dinner, your penthouse features a fully equipped kitchen with a breakfast bar, a formal dining area inside with seating for six, and an alfresco set on the balcony with space for four. There’s also a barbecue on the balcony, in case you feel like grilling up something fresh from a local market. Wailea Beach’s white sandy shores and calm, crystal clear waters are ideal for first-time snorkelers, kayaking, and other water sports. It’s a relaxing environment for adults, and the water is calm enough for kids to play in. If you’re interested in a round of golf, The Wailea Blue course is a spectacular eighteen-hole that weaves its way through the resort, offering scenic views of the ocean, neighboring islands, and Mt. Haleakala. For shopping, The Shops at Wailea is an open-air mall with over sixty outlets, art galleries, and restaurants. Copyright © Luxury Retreats. All rights reserved. HAWAII TAX ID #: 185-759-1296-01 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, Shared access to hall bathroom with stand-alone shower, Dual vanity, Television, Air conditioning, Ceiling fan Additional Bedding • Office: Queen size sofa bed, Ceiling fan, Desk FEATURES & AMENITIES • Ocean view • More under “What this place offers” below Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Dec 5 – 12

$3,171 per night

Popular amenities for Wailea, Wailea-Makena luxury vacation rentals

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

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