Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui
Wailea is Maui's most refined resort area, offering a curated selection of luxury vacation rentals. Choose from spacious oceanview condos, private beachfront villas, or gated residences-each within walking distance to top beaches like Wailea Beach, Polo Beach, and Ulua Beach. With championship golf, fine dining, luxury spas, and The Shops at Wailea nearby, Wailea is perfect for honeymoons, family vacations, and long-term stays.
Browse Wailea Vacation Rentals by condo/hotel name:
Wailea vacation rentals combine the comfort of home with the indulgence of resort amenities. Whether you prefer a villa with sunset views, a quiet garden retreat, or a beachside condo steps from the surf, Wailea's neighborhoods cater to every kind of traveler.
Top Wailea Vacation Rental Communities
Oceanfront and Beach Access Villas
- Wailea Beach Villas – oceanfront penthouses and beachfront villas
- Polo Beach Club – beachfront condos with panoramic views
- Wailea Point Village – gated luxury with prime oceanfront location
- Mana Kai Maui – beachfront condos on Keawakapu Beach
- Wailea Elua Village – beachfront property with pavilion and pools
Resort-Style Villas & Upscale Condos
- Ho'olei at Grand Wailea – spacious 3-bedroom villas with cascading pool
- Wailea Ekahi Village – low-rise condos with ocean views and tropical gardens
- Wailea Ekolu Village – hillside condos near golf and beaches
- Wailea Grand Champions Villas – golf course condos with pools
- The Palms at Wailea – Mediterranean-style condos with large lanais
Why Stay in Wailea?
- Access to Wailea Beach, Polo Beach, and Keawakapu Beach
- Home to Wailea Golf Club and scenic coastal trails
- Upscale dining and retail at The Shops at Wailea
- Quiet, landscaped communities perfect for long stays
- Consistently sunny weather and calm swimming beaches
Plan Your Stay in Wailea
Wailea offers the best of South Maui-tranquil surroundings, world-class amenities, and stunning natural beauty. Whether you're visiting for a romantic retreat or a long-term tropical escape, Wailea vacation rentals provide the perfect home base for a luxurious island experience.
Tiki Tiki - A Gorgeous Boho Beach Hideaway!
Fall in ALOHA with Tiki Tiki!! This special studio is truly a piece of Paradise!A magical retreat that will have you feeling zen & refreshed. Tiki Tiki is the perfect home for honeymooners, girlfriend getaways, or any adults looking for a tropical stay in the the heart...
🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
Wailea Grand Champions Villas -- Condo #188Aloha!You are coming to Maui for your Dream vacation---Why not stay in a Tranquil, spacious condo full of High-end amenities while enjoying the island? We welcome you to share our well-loved Maui paradise in stunning Wailea!...
Impressive Wailea Ekahi 1 Bd+2Ba Condominium 20G-Adjacent to Keawakapu Beach
Ekahi 20G - newly remodeled as of July 2025. Gorgeous! Professional photos pending.Stay with Wailea Rentals at Wailea Ekahi Village 20G. You and your guests will enjoy premier accommodations, furnishings and holiday experiences at this top-floor Wailea Ekahi vacation...
Wailea Grand Champions | 183
Welcome to Wailea Grand Champions 183, a luxurious vacation rental that perfectly blends comfort and style in the heart of Maui's paradise. This stunning two-bedroom, two-bathroom retreat offers an exceptional experience for discerning travelers seeking a memorable...
125+ 5star REVIEWS SAYS IT ALL! Golf & Ocean! LAST MIN CANCL APRIL! 169 +tx rate
Location: Grand Champions, Wailea, South Maui, Maui, Hawaii, USA (2 miles Kihei, 13 miles airport, 1/2 mile beach.) Accommodations: Condominium, 1 Bedroom, 2 Baths (Sleeps 2) Maximum occupancy is 2 adults 25 years old or older onlyCOME ENJOY OUR FULLY RENOVATED FROM...
STUNNING NEW REMODEL-SUNSETS-LUXURY-QUIET LOCATION-AC-LARGE LANAI
Book with confidence, this stunning, 1 bedroom, 2 bathroom (1022 sq. ft) condo that has been completely remodeled from top to bottom with modern finishes, where even the lanai sliding doors were replaced. This condo is managed by PMI Maui, a local Real Estate Brokerage...
Wailea Elua 3 Bedroom+2 Bath Spacious Beach Home with Oceanview Lanai
This is the one! A real Maui home-away-from-home. If you are looking for an impressive vacation home with new Ohia wood cabinets, cupboards, and accents in the kitchen, new sandstone tile flooring, super quiet new Fleetwood glass doors, new Miele appliances, and new...
Wailea Elua: Huge Ocean Views, Pool, AC & Hot Tub
Summary:Nestled in the scenic beauty of Wailea, this inviting condo promises a delightful escape with everything you need for a memorable stay. Imagine waking up to ocean views, leisurely days by the pool, and evening strolls along the beach. This is a place where you...
Palms at Wailea 1904! Nicely updated and great Wailea location!
Palms at Wailea 1904 is a nicely updated and well-located 2-bedroom, 2-bathroom condo in the beautiful area of Wailea. This condo is the perfect getaway for families or couples traveling together. It features a private lanai with lush garden views, making it a great...
Stunningly Renovated! Ocean View! Elua 2305
This property is hotel zoned, and not being affected by the recent proposed legislation.Welcome to Elua 2305. Your ultimate Maui vacation awaits at this fabulous listing! Don’t miss this incredible opportunity to enjoy the very best that Maui has to offer.Say Aloha to...
Wailea Ekolu Village | 706
Towering oleander and bougainvillea grace the front entry of Wailea Ekolu 706. Enjoy views out over the tropical grounds and beyond from the elevated second floor positioning of this condo. During the winter months, you can whale watch right from the lanai as you gaze...
Wailea Ekahi 40A - 5-Star South Maui Oasis
Welcome to your piece of paradise in a completely remodeled, fully furnished, ground floor unit! Our home is located in Wailea Ekahi, one of the few Kihei and Wailea properties located directly on the beach; no need to cross a road or even sidewalk!Our private corner...
Wailea Ekolu Village | 1107
Wailea Ekolu 1107 is a charming ground-floor vacation rental that offers the perfect blend of convenience and stunning views of the ocean, mountains, and the island of Lana'i. Guests can enjoy the soothing sounds of tropical birds without the disturbance of street...
Wailea Elua Village | 1703
Elua 1703 is a distinctive oceanfront vacation rental, perfectly situated directly in front of the renowned Ulua Beach and the Wailea Beachfront Walking Path. What sets it apart is its unique privacy, surrounded on three sides by lush, meticulously landscaped gardens...
Wailea Ekolu Village | 1607
Wailea Ekolu 1607 is a stunning one-bedroom, two-bathroom vacation rental that offers an exceptional escape in beautiful Wailea. This beautifully appointed condo features calming views of the lush landscapes of the Wailea Blue Golf Course, providing a serene backdrop...
Wailea Elua 803 - Ocean Views, Modern Renovation, Central AC, Wi-Fi, BBQ Grill
Every detail was addressed in the complete and total renovation of this single-level luxury condo at Wailea Elua Village. Upon entering Wailea Elua Village unit 803, you are immediately greeted with panoramic ocean views from the open living area, and the unit is...
Wailea Elua Village | 905
Wailea Elua 905 is a vacation rental situated in the picturesque beach locale of Maui. This spacious three-bedroom, two-bathroom condo offers a perfect blend of comfort and luxury, making it an ideal retreat for families or friends traveling together. This condo is...
New Listing- Impressive 3 Bd+2 Bath Vacation Home at Wailea Grand Champions
Bldg. 16 - Unit #153 - A front-row, ground floor, impeccable 3 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is a prime example of what Wailea Grand Champion Golf Villas has to offer in a 3 bdrm + 2 bath category. Upgraded...
Makena Surf | F109 | Beachfront Resort
Makena Surf F109 is a stunning oceanfront vacation condo that places you just steps away from the beautiful shores of Maui. With nothing but a lush patch of green grass separating you from the ocean, this ground-floor unit offers breathtaking views that you can enjoy...
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
**FAMILY FRIENDLY**If you are looking for a modern, luxurious retreat in Wailea with BRAND NEW EVERYTHING, look no further! This unit was completely gutted to the studs and every item was purchased brand new. Guests can enjoy:— Modern, deluxe kitchen with all new...
Polo Beach Club | 409
Polo Beach Club 409 is a luxurious oceanfront vacation rental located in the world-renowned beach vacation destination of Wailea. This two-bedroom, two-bathroom condo offers a premium beachfront experience with direct access to Polo Beach out front and stunning ocean...
Immaculate, Luxury Comfort, Stunning Views - Hawaiian-Chic, Mid-Century Modern
Experience the beauty of Wailea from the moment you arrive in your spacious and stylish villa. Situated in a secluded position of the Grand Champions resort property you can relax on the lanai and take in the views, get to that book you’ve been meaning to read, or...
Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!
Boasting stunning panoramic views of the Pacific Ocean that extend deep into the home's living, kitchen, and dining areas, Wailea Elua 2204 is a luxuriously renovated second-floor villa featuring some of the most spectacular vistas South Maui has to offer. Watch...
Makena Surf | F304 | Beachfront Resort
Makena Surf F304 is a stunning oceanfront vacation rental located in the beautiful Makena region of Maui, Hawaii. This luxurious third-floor condo offers breathtaking views of the Pacific Ocean and is perfect for families or couples seeking a relaxing getaway.The...
Wailea Beach Villas | PH104
Marvel at the sophisticated style and décor of Wailea Beach Villas Penthouse 104, where a touch of Bali influence seamlessly merges with rustic undertones to create an unforgettable ambiance. The interior design captivates with elements like a textured wall-mounted...
Amazing view, Close to the beach, Wailea Ekahi Unit 20i
Condo 1 bedroom, 2 bath (sleeps 4)PRIME location on the front row in lower Wailea Ekahi, Wailea. Listen to the sound of the waves and enjoy the ocean views. Famous Keawakapu Beach is just steps away! Beautiful ocean views from every room. Enjoy the extra-large lanai...
Impressive 2 Bdrm+2 Ba Paradise Condominium at Wailea Grand Champion Villas
Treat yourself to an impeccable Front-Row 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is the finest that Wailea Grand Champion Golf Villas has to offer in a 2 bedroom + 2 bath category. Upgraded in every way with split A/C...
nNEW KITCHEN REMODEL! Amazing View!
Condo, 1 bedroom + other (See Description) 2 baths (Sleeps 4)Peace of mind is important for where you are staying. Our cleaning care professionals have been trained to properly follow all CDC, VRHP (Vacation Rental Housekeeping Professionals) and VRMA (Vacation Rental...
You'll Love The Ocean Views! 5 Star Hospitality! Hoʻokipa at Wailea Ekolu.
ALOHA!Immerse yourself in the warmth of Aloha at Our Maui Condos - Ho'okipa at Wailea Ekolu Village. Discover the true meaning of Hoʻokipa through our exceptional Wailea Ekolu home. Enjoy breathtaking Maui sunsets with panoramic views of Molokini and Kahoolawe.Our...
Wailea Beach Villas | PH201
Call this private piece of paradise home, which features panoramic views of Maui and the ocean below as well as luxurious interior elements everywhere you look. This contemporary vacation residence spans 2,500 square feet and captures the true allure of vacationing in...
Wailea Ekahi Village | 23C
Welcome to Wailea Ekahi Village 23C. This residence was fully renovated in the fall of 2024 and features beautiful furnishings and decor to offer you a relaxing, island-inspired retreat. Nestled within 34 acres of lush tropical landscaping, 23C is a ground-floor...
Wailea Beach Villas | PH207
Upon entering your Wailea Beach Villas PH207, you'll be captivated by the open floor plan, which seamlessly integrates a cozy living room, a quiet den with shoji screen doors, a gourmet kitchen, and a dining area. Sliding doors lead to a lanai equipped with a built-in...
NICELY UPDATED-SLEEPS 8-WELL EQUIPPED-AC-METICULOUS CLEANING
Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that has been nicely updated. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available 24/7...
The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
The Maui Escape is located with views of the upper pool and the spectacular surroundings. The villa's location is the perfect combination of being close enough to view the pool but far enough for privacy. At night the ambiance from the lanai is breathtaking with...
Wailea Beach Villas | PH411
Let the sounds of palm fronds brushing against each other in the gentle trade winds sing you to sleep this vacation. With relaxing views of the ocean and the manicured tropical landscaping, Wailea Beach Villas Penthouse 411 leaves no stone unturned in the pursuit of...
Wailea Elua Village | 107
Located just steps from the beach in the heart of Wailea, Elua Village 107 is a beautifully appointed two-bedroom, two-bathroom ground-floor residence that offers the perfect blend of comfort and island elegance. With a spacious layout and tasteful décor, this vacation...
NEWLY REMODELED-QUIET LOCATION-AC-WELL EQUIPPED-METICULOUS CLEANING
Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that was just completely remodeled with all new furnishings. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of...
PURE ELEGANCE*OCEANVIEW Renovated Condo in WAILEA
For travelers seeking luxury and an escape from life in the resort town of Wailea, this complex is one of the most exclusive sanctuaries. The newly renovated 1536 square foot condo is a spectacular beachfront vacation rental with panoramic ocean views and extensive...
Wailea Beach Villas | PH502
Wailea Beach Villas Penthouse 502 boasts a panoramic ocean vista, ideal for whale watching in the winter, and with spectacular sunset views all year long. This top floor penthouse has been exquisitely redecorated with an elegant, casual décor.Your private elevator...
Luxurious, 2 bedroom / 2 bath, FULL Ocean View Wailea Condo
Situated on 18 acres of perfectly manicured tropical foliage, bordering the award winning Wailea Blue Golf Course, Ekolu Village is an exclusive and desirable complex that is exceptionally quiet and free of any traffic noise. This property is located in less than a 5...
Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025
Remodel completed June 2025! See the new photos just posted!The entire home has been repainted, almost all the furniture was replaced, a lot of new beautiful art was added, and all new hardwood French oak floors were installed in the bedrooms.. We also remodeled the...
MODERN MAUI I404! - MODERN LUXURY AND PANORAMIC OCEAN VIEWS
Private Paradise Villas personally manages 19 exceptional villas within this award-winning location, offering a curated and exclusive collection of 2.5 to 4 bedroom villas, most with panoramic ocean views. Private Paradise Villas is in part responsible for the recent...
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
The Maui Meadows Guesthouse Property is 3/4 mile from (8) premier beaches and features: (4) Bedroom, (5) Bath one story 2700 sq ft house, Proximity to beaches, activities, golf, shopping, restaurants and bars, Air conditioning, 65" TV screen with Streaming TV with NFL...
OCEANVIEWS, FRESH UPGRADES AT THE LUXURIOUS GRAND SEASCAPE K407!!
Situated in the centrally located "Penthouse" building on the 4th floor in a west-facing ocean view corner location with breathtakingly beautiful panoramic ocean and sunset views, this 2.5 bedroom (king bed in each bedroom plus 2 twin beds the enclose-able den that can...
Wailea Elua 1101 - Beachfront Section - Ocean View -1 Bedroom &NewQualitySofaBed
We are a 1 minute walk from the amazing Ulua Beach. You can see and hear the ocean from our condo. Relax viewing the ocean on a private, quiet lanai surrounded by tropical gardens. Earth-friendly furnishings and complete “green” remodel. Gourmet kitchen, spacious...
No stairs inside or out! Beautifully remodeled Palms at Wailea 503
Please note the pool and hot-tub will be closed for maintenance Sept 16-19, 2025, reopening Sept 20, 2025.Welcome to Palms at Wailea 503, your beautifully remodeled sanctuary in paradise! This is a two-bedroom two-bathroom condo in the prestigious Wailea Resort area....
Luxe Townhome, Ocean Views, Relax by the Pool
- Luxurious two-story townhome with a private elevator and sleeps 10 comfortably- One of the few villas offering both pool and ocean views- Prime location near the pool and just minutes from the beach- Hotel-quality beds with luxury linens- Private lanai with seating, a...
KBM Resorts | FREE CAR | Wailea Beach Villa | Spacious 3-Bedroom Condo with Sweeping Ocean view! WBV-PH412
Oceanview 3-bedroom, 3-bath penthouse at Wailea Beach Villas with monkeypod cabinetry, spacious lanai, & luxury finishes. Includes rental car with 6+ night stays booked through 2025.** Limited Time Special Offer: Book any KBM rental home in Hawaii for 6 nights or more...
Elegant, Bright Remodel! Tropical Views! Ekahi 40D
Located just moments away from the pristine beaches, this elegant condo offers the perfect balance of tranquility and convenience. Explore the nearby attractions, engage in water sports, or simply lounge by the pool and soak up the sun.Welcome to our exquisite...
Maui Banyan #G-309 Ocean View 2-bedroom condo in fabulous Kihei
Located in the heart of Kihei, this condo is a dream. With 2 bedrooms featuring two king beds with ceiling fans, Queen size sleeper sofa in Living room, 2 bathrooms with rainfall showers. A chef's kitchen fully stocked with many culinary appliances. It also includes a...