Luxury rentals in Wailea
Find and book unique accommodation on Airbnb
Top-rated luxury holiday rentals in Wailea
Guests agree: these stays are highly rated for location, cleanliness and more.
Blue Sky Villa
Blue Sky Villa in Maui has been designed and decorated to soothe your mind, body and soul. This magical villa brings you close to the setting of the ancient Hawaiian kings with architecture that swirls and soars in the manner of the ocean and sky before it. Within easy walking distance to Lahaina Town and a short drive to the beaches, Blue Sky Villa also offers a convenient location for exploring this spectacular island. This resplendent villa features one of the finest lap pools in all of Hawaii. Step into the soothing bubbles of the outdoor hot tub for a special treat. Indoors, you will find a media room, Wi-Fi access, ceiling fans and laundry facilities. Step onto the splendid balcony and ascend the open air winding stairs to your private meditation tower reminiscent of an ancient castle suffused on all directions by ocean and mountain vistas including Lanai, Kahoolawe, and the sublime peaks and contours of Pu’u Kukui. The grace and beauty of the outdoors at Blue Sky Villa are only matched by its pristine and vast interiors. This luxury house was built to enjoy the natural beauty and breezes of Maui, enabling the ultimate indoor/outdoor living experience. Doors fully retract in the master bedroom as well as the living and dining rooms. The living room features a white baby grand piano that awaits the life breath of music. This villa includes a premiere master bedroom where one feels as though they are floating on a cosmic ship of azure. The refined luxury of the master bathroom will take your breath away. There are four additional bedrooms with equal comfort and four additional bathrooms. This villa accommodates up to twelve guests. During your stay at Blue Sky Villa, you will be just a short drive away from Lahaina, Baby and Ka’anapali beaches. Both surfers and golfers will be in paradise as they explore their options in this iconic landscape. Nearby Lahaina is a heritage town transformed into a modern Maui hot spot. Lahaina offers a variety of unique art galleries, shops and restaurants. A historic 1800s whaling village, this area has been immortalized by Herman Melville in the classic Moby Dick. The delights of Maui await! Copyright © Luxury Retreats. All rights reserved. Permit #: STWM 2014/0002 HAWAII TAX ID #:051-843-4816-01 BEDROOM AND BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite open-air bathroom with rain shower and soaking bathtub, Dual vanity, Walk-in closet, Air conditioning, Lounge area, Television, Ceiling fan, Lanai, Outdoor furniture, Ocean view • Bedroom 2: King size bed, Shared access to bathroom with bedroom 3, Shower/bathtub combo, Air conditioning, Television, Ceiling fan • Bedroom 3: Queen size bed, Twin size bed, Shared access to bathroom with bedroom 2, Shower/bathtub combo, Air conditioning, Television, Ceiling fan • Bedroom 4: King size bed, Ensuite bathroom with shower/bath combo, Air conditioning, Television, Ceiling fan • Bedroom 5: Queen size bed, Ensuite bathroom with shower/bathtub combo, Air conditioning, Television, Ceiling fan, Balcony FEATURES AND AMENITIES • Private meditation tower OUTDOOR FEATURES • Lanai STAFF & SERVICES Extra cost (advance notice may be required): • Massage therapist • Activities and excursions • Mid-stay cleaning
Ocean Views | Polo Beach Club | Groundfloor Condo
Step straight onto the sand at Polo Beach—Wailea’s premier swimming beach—from this rare ground-floor condo with ocean views that will take your breath away. Located in the exclusive Polo Beach Club, this 2-bedroom retreat offers near-private beach access, a walkout lanai, and unbeatable proximity to Maui’s top coastal path. Inside, unwind with a chef’s kitchen, spa-style bathrooms, Moccamaster coffee, and Dyson Airwrap. This is five-star comfort, with the beach at your doorstep.
Wailea Hoolei 93-3 Rarely Priced for Last Minute
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays. Welcome to Ho‘olei 93-3, a lavish 3-bedroom, 3.5-bath villa nestled in the private, gated enclave of Ho‘olei, just a short stroll from world-famous Wailea Beach and the iconic Grand Wailea Resort.
KBM Resorts | FREE CAR Kapalua Bay KBV-34G4
Luxurious oceanfront villa with panoramic Molokai views, private lanai, gourmet kitchen, and spa-inspired master suite-perfect for a relaxing Maui escape with comfort, style, and island charm. Please note that this listing can accommodate up to 4 guests, with additional bedding provided via a sofa bed in the living room.
Wailea Hoolei 23-3 Your Ultimate Luxury 3Bedroom
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays. Welcome to Ho‘olei Residence 23-3 (L3), a show-stopping 3-bedroom, 3.5-bath villa set within Wailea’s coveted, gated Ho‘olei enclave on Maui’s sun-kissed south shore.
Just Steps from Maui's Best Beach! Pool and slide
BRAND NEW CONSTRUCTION finished in Sept 2018! No expense was spared in this beautiful 1800 square foot gated and private home. Just 40 steps to Maui's best sandy beach (perfect for family swimming and very kid friendly), this home literally has something for all ages.
KBM Resorts | FREE CAR Montage Kapalua MON-6301
Luxurious ocean view 3-bedroom, 3.5-bath Grand Residence at Montage Kapalua Bay, gourmet kitchen, spacious lanais, and convenient beach and pool access.
Garuda Estate Maui
3br/3ba + bonus office with all-in-1 printer, sofa bed & TV. Oceanview home with a pool, hot tub, and Ocean Views!
Paradise Cove
Short term rental permit #STWM20200001 Tax Map Key (TMK) (2) 4-3-007:015
Haiku House Maui
Maui County Permit # CP 2015/0007. Tax Map Key (2)2-7-003:87
Hale Makena Maui
Contemporary designer villa with beach views
Napili Cove
Tropical Beach Retreat in Maui, Hawaii
Popular amenities for Wailea luxury holiday rentals
Other great luxury holiday rentals in Wailea
Paradise Cove
KBM Resorts | FREE CAR Kapalua Bay KBV-34G4
Ocean Views | Polo Beach Club | Groundfloor Condo
Wailea Hoolei 93-3 Rarely Priced for Last Minute
Hale Makena Maui
Blue Sky Villa
KBM Resorts | FREE CAR Montage Kapalua MON-6301
Napili Cove
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.
Keen snorkelers will enjoy White Rock beach, a popular spot with the island’s inhabitants. There’s great underwater visibility, which makes spotting sea life a pleasure. There’s no amenities here but if you’re after something more laid-back and local, you’ve found it.
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
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
- Apartment rentals Wailea
- Rentals with a sauna Wailea
- Family-friendly rentals Wailea
- Rentals with beach access Wailea
- Rentals with outdoor seating Wailea
- Serviced apartment rentals Wailea
- Beach apartment rentals Wailea
- Fitness-friendly rentals Wailea
- Pet-friendly rentals Wailea
- Beachfront rentals Wailea
- Rentals with a hot tub Wailea
- Hotel rentals Wailea
- Cottage rentals Wailea
- Flat rentals Wailea
- Waterfront rentals Wailea
- Rentals with a kayak Wailea
- Rentals with pools Wailea
- House rentals Wailea
- Rentals with a washing machine and dryer Wailea
- Rentals with an EV charger Wailea
- Villa rentals Wailea
- Rentals with a patio Wailea
- Townhouse rentals Wailea
- Luxury rentals Wailea
- Luxury rentals Maui County
- Luxury rentals Hawaii
- Luxury rentals United States
- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Honolua Bay
- Sandy Beach
- Kapalua Bay Beach
- Spreckelsville Beach
- Olowalu Beach
- Pahoa Beach
- Manele Golf Course
- Maui Ocean Center
- Wailea Beach
- Hāmoa Beach
- Oneloa Beach
- Kaipukaihina
- Puu Olai Beach
- Changs Beach
- Palauea Beach
- Old Lahaina Luau
- Wailau Valley
- Polo Beach
- Wailea Golf Club
- Maui Golf & Sports Park