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.
Wailea Beach Villas Penthouse K107 – Maui Luxury with Island Serenity
Welcome to Wailea Beach Villas Penthouse K107 - A luxurious and spacious 2-bedroom, 2-bath with a den that functions as a workspace or third bedroom offering 1,899 square feet of elegant island living.Perched directly above the upper pool, this villa enjoys lush...
Ground-Floor Gem in Wailea Ekahi Village
Discover true island elegance in this beautifully updated ground-floor residence at Wailea Ekahi Village, one of Maui’s most sought-after beachfront communities for vacation renters. Set within 34 acres of lush, low-density tropical gardens, the property offers direct...
Sunset Views | Whale Watching | Resort Amenities - Wailea Point 3203
Wailea Point #3203 offers a luxurious and serene retreat with stunning ocean views, located in the exclusive gated community of Wailea Point. This elegant condo is perfect for those seeking privacy and a minimum stay of 30 nights, providing an ideal setting for a...
Golfer's Dream | Condo on Wailea Course
Wailea Grand Champions 31 is a recently updated vacation rental that offers a perfect blend of comfort, style, and convenience in the heart of Wailea. This two-bedroom, two-bathroom condo features modern upgrades including granite countertops, new cabinetry, and...
Spacious Condo in Heart of Wailea
Wailea Grand Champions Villa 111 is a spacious two-bedroom, two-bath vacation rental condo that accommodates up to six guests, making it an ideal choice for families or friends traveling together. The first bedroom features a comfortable king-sized bed, while the second...
Golfer's Dream | Condo on Wailea Course
Villa 104 at Wailea Grand Champions Villas is a beautiful Maui vacation rental that offers an exceptional blend of style, comfort, and convenience. This modern and hip condo boasts stunning golf course views and thoughtfully curated interior design elements that create...
Walk to Waves, Snorkeling, Pool - Wailea Elua 910
Wailea Elua Village 910 is a stunning one-bedroom, one-bathroom vacation rental located in the exclusive Wailea community on Maui. This beautifully remodeled condo offers a luxurious retreat a short stroll to one of the best snorkeling beaches on Maui. Located on the...
Modern Renovation with Ocean Views | Wailea Elua 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...
Wailea Beach Villas PH502 - Professionally Managed
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...
Recently Renovated at Wailea Beach Villas
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...
Walk to Wailea Beach & Shops at Wailea
Wailea Beach Villas PH410 is a fourth floor penthouse suite that overlooks the central swimming pool with spectacular views of the Pacific Ocean and Wailea Beach, along with views of Kahoâolawe, Molokini and Lana\'i. From your private elevator landing, the suite opens...
Panoramic Ocean Views - Wailea Beach Villas PH406
Wailea Beach Villas Penthouse 406 is desirable for its remarkable Pacific Ocean and Island views. This upscale penthouse vacation rental features two bedrooms, two bathrooms, exotic hardwood furnishings, an incredible antiquities collection, and an amazing ocean view....
Bright & Colorful Ocean View Villa | Wailea Beach Villas PH402
Experience the very best in tropical island living from ocean view Wailea Beach Villas Penthouse 402. Revel in sweet sunsets and seasonal whale watching from your spacious, private lanai with scenic views of the Maui horizon, Molokini Crater and the island of...
3BD Wailea Villa - Great for Families | Wailea Beach Villas PH309
Penthouse 309 at Wailea Beach Villas offers a distinctive blend of luxury and cultural charm, making it an ideal vacation rental for families or groups of friends. This 2,520 square foot ocean view suite is located on the third floor and is accessible via a private...
Wailea Villa in Top-Rated Hawaii Resort
Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms designed with tropical island elegance. This vacation rental welcomes families with its spacious layout, offering stylish...
Wailea Villa Overlooking Lagoon Pool
Welcome to Wailea Beach Villas Penthouse 209, a beautifully furnished 2,600 sq. ft. garden view suite that offers a serene escape overlooking the family pool. This open and airy vacation rental is designed for relaxation and leisure, featuring an expansive tiled great...
Floor to Ceiling Ocean Views - Wailea Elua 2006
Wailea Elua Village 2006 is a charming vacation rental that epitomizes the luxury and tranquility of Maui. This beautifully appointed two-bedroom, two-bath condo offers an ideal retreat for families or friends seeking a relaxing island escape. The residence boasts a...
Walk to Wailea Waves, Snorkeling, Restaurants
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 Elua 2004 | Hot tub | Pool | Sunset Views
Wailea Elua 2004 is a luxurious vacation rental located along the shores of Maui\'s southern coastline. This one-bedroom, one-bathroom condominium offers an ideal retreat for couples or small families, featuring a spacious layout that maximizes comfort and ocean views...
Elevated Beachfront Views - Wailea Elua 1704
Wailea Elua 1704 is a stunning oceanfront vacation rental located a short stroll from one of the top snorkeling beaches on Maui. This spacious two-bedroom, two-bathroom corner unit spans approximately 1,600 square feet and comfortably accommodates up to six guests,...
Penthouse Retreat | Walk to Wailea Beach
Curated with our guests in mind, Wailea Beach Villas PH111\'s outdoor elements are just as immaculate as the homeâs interiors. Unwind and enjoy peekaboo views of the ocean along with tropical greenery from your private lanai. The pristine Wailea Beach is located...
Recently Renovated - Oceanfront in Wailea
Expansive unobstructed views of blue Pacific waters and gentle waves will greet you each time you step out onto the lanai and soak in all the beauty that Wailea Elua 1604 offers. Evenings offer gorgeous sunsets framed by swaying coconut palms, perfect for a relaxing...
Voted Top 10 Resort in Hawaii - Wailea Beach Villas F201
Welcome to Villa F201, an expansive vacation retreat that embodies upscale relaxation. Spanning a generous 3,676 square feet, this luxurious 3-bedroom, 3.5-bath villa is perfect for families or couples seeking a serene getaway. Villa F201 is a decorator\'s dream,...
Conde Nast Award Winning Property - Wailea Beach Villas E202
Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointed interior blends seamlessly onto the private outdoor lanai. Contemporary neutral and earth-toned furnishings are complimented by splashes of color...
Recently Renovated | Wrap-Around Ocean Views | Wailea Beach Villas D302
Welcome to Wailea Beach Villas D302! Recently renovated, this residence features a custom gourmet kitchen and dining area, offering a luxurious and spacious retreat in one of Maui\'s premier locations. Spanning over 2,900 square feet of indoor and outdoor living, it...
Prime Location | Snorkeling | Wailea Beach Path
Wailea Elua 1203 is a stunning one-bedroom, one-bathroom oceanfront vacation rental located on the ground floor of the prestigious Wailea Elua Village community. This condo offers direct access to Ulua Beach, where guests can enjoy swimming and snorkeling in the gentle...
Spacious Wailea Condo - Professionally Managed - Ekolu 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...
Ocean Views | Close to Wailea Golf & Beaches
Experience the beauty of Maui at Wailea Ekolu 1007, a stunning two-bedroom, two-bathroom ocean view condo designed for relaxation and comfort. Located along the picturesque Wailea Blue Golf Course, this ground floor vacation rental offers breathtaking views of the lush...
Sunset Ocean Views | Whale Watching | Wailea Ekahi 38B
Enjoy a relaxing indoor/outdoor tropical vacation experience from this ground floor ocean view vacation rental. Start your morning on the lanai with a freshly brewed cup of coffee and walk out on the sprawling grass lawn to feel the soft grass beneath your toes. Take in...
Wailea Ocean Views | Great for Families
Wailea Ekahi Village 19B is a two-story, two-bedroom, two-and-a-half-bath townhome that comfortably accommodates up to four guests. This beautifully designed residence features island-inspired decor, creating a cozy and inviting atmosphere perfect for families or...
Wailea Ekahi Village 12C - 1 Bedroom Ocea View Condo
Wailea Ekahi 12C is a beautiful vacation rental nestled within the landscaped 32 acres that make up Wailea Ekahi Village. This upgraded condo offers a perfect blend of comfort and tropical elegance, making it an ideal retreat for those looking to escape the hustle and...
Wailea Ekahi 11C | Snorkeling & Waves Out Front
Wailea Ekahi 11C is an ideal Hawaiian retreat for friends or families traveling together. Each of the two bedrooms in this spacious condo feature a private lanai and en suite bathroom. Many guests return to this condo year after year for its close proximity to the pool...
Walk to the Beach - Wailea Ekahi 10F
Wailea Ekahi Village 10F is a premier vacation rental located in the heart of Wailea, Maui. This one-bedroom, two-bathroom condo is part of the Wailea Ekahi Village, a low-density community set across 34 acres of meticulously landscaped tropical gardens. The condo...
Golf Course View Retreat | Wailea Condo GC100 | Walk to Shops & Beaches
Welcome to Grand Champions #100, a meticulously updated 2-bedroom, 2-bathroom villa located in the heart of Wailea. Overlooking the 3rd hole of the Wailea Blue Golf Course, this spacious retreat features vaulted ceilings, modern upgrades, and spectacular views of...
Wailea Ekahi 24B - Modern Garden Retreat w/ Lanai, Split AC & Stylish Renovation
Nestled on the ground floor, Wailea Ekahi 24B is a beautifully remodeled one-bedroom, two-bath condo featuring a sleek, modern design and effortless indoor-outdoor living. With elegant finishes throughout, including quartz countertops and stainless-steel appliances,...
Wailea Elua 808 - Scenic Ocean Views, Classic Wailea Charm, Central AC, Wi-Fi
Welcome to Wailea Elua 808, your ideal Maui retreat. This spacious 2-bedroom, 2-bath condo offers the perfect setting for a relaxing getaway or a family vacation. With a thoughtfully designed floor plan, stylish furnishings, and ample natural light, you'll feel at home...
Wailea Elua 2007 – Oceanview Luxury Condo in the Heart of Wailea
Welcome to Wailea Elua 2007, a stunning 1-bedroom, 2-bath vacation retreat with gorgeous ocean views, a spacious private lanai, and upscale island furnishings throughout. Perfectly positioned within the prestigious Wailea Elua Village, this beautifully appointed condo...
Luxury Oceanview Wailea Retreat with Sunset Views
Escape to Hōkū Hale, a serene oceanview retreat in the heart of Wailea. This designer oasis offers modern comforts, a private lanai with stunning ocean views, on the fairway of a private golf course. Walk to world-class beaches, dining, golf or relax in a peaceful,...
Lovely Palms at Wailea condo, spacious, large lanai, close to beach! Full A/C
Located in the highly desirable Palms at Wailea, this delightful condo offers a relaxing retreat for guests. This spacious condo sleeps 4 with 1 bedroom featuring a king bed and a queen size sofa bed in the living room. It also has two full bathrooms. It's upstairs...
Wailea Oceanfront Center Front Row Luxury Retreat
Immerse yourself in the beauty of Maui at this stunning oceanfront property. This 2-bedroom, 2-bathroom condo offers center unit front row access of the Pacific Ocean.The primary bedroom features a king-sized bed with direct access to the lanai. The second bedroom...
Modern Spacious Beachfront Luxury in Wailea. Family Friendly!
A modern 2 bedroom, 2 bath condo with extra bunk beds and an amazing ocean view!South Maui is one of the most beautiful destinations in all of Maui and Wailea Ekahi Village is a perfectly situated, beachside resort we call home. Guests return to Ekahi year after year to...
Wailea Elua 1304 - Spectacular Oceanfront Condo with Panoramic Views
Wailea Elua #1304 – Oceanfront Comfort in the Heart of Wailea’s Resort CommunityWelcome to Wailea Elua #1304, a beautifully appointed 2-bedroom, 2-bathroom oceanfront condo offering the perfect blend of luxury and relaxation. Nestled in one of Wailea’s most exclusive...
Wailea Elua #2107 - Spacious, Stylish & Just Moments from Wailea Beach
Wailea Elua #2107 – Your Serene Wailea EscapeWelcome to Wailea Elua Village, a peaceful, terraced beachfront property located in the heart of the Wailea resort community. This low-density gated complex features two-story buildings set on 24 acres of lush tropical...
WE 907 Breathtaking Ocean Views from the Top of Wailea 2BD Amazing Location
Wailea Ekolu 907 NEW LISTING! Discover the luxury and beauty of Wailea from this spacious, well-appointed 2-bedroom, 2-bathroom condo at Wailea Ekolu Village, Maui. Expansive ocean views set the perfect panoramic backdrop for an unforgettable Maui experience. Enjoy...
Receive a $100 Gift Card for Snorkel Gear or Wailea Dining Options!
*Absolutely Stunning Panoramic Ocean and Island Views*Yards Away from Local Favorite Shops and Dining*4 beaches within 1-2 miles (Wailea, Ulua, Mokapu, Keawakapu Beaches) Experience paradise at Wailea Ekolu 104, where breathtaking panoramic ocean views and spectacular...
Stunning ocean view! 2/2 in the heart of Wailea
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning...
Large Ocean View 2-bedroom condo with AC and WiFi in wonderful Wailea-Makena
Enjoy the comfort and cleanliness of your own space. Located in the heart of Wailea, Grand Champions Villas is next to a golf course, tennis courts, a short walk from the Shops of Wailea, restaurants and a 5 minute drive to Wailea Beach. Open floor plan living area...
Oceanview Serenity Meets Modern Comfort: Discover Wailea Ekolu #402
Wailea Ekolu #402 – Your Serene Wailea EscapeEscape to paradise at Wailea Ekolu #402, where stunning ocean views, serene surroundings, and the spirit of aloha combine to create the ultimate Maui getaway. Nestled above Wailea’s world-famous beaches and golf courses, this...
Wailea Ekolu 1207 2 Bedroom 2 Bath Condo
Relax at our quiet 2 bedroom /2 bath condo with stunning views overlooking the Wailea Blue golf course all the way to the ocean. Guests can enjoy amenities like a washing machine, AC, and WiFi during their stay. We hope you'll enjoy your stay at our condo.
180 Degree Ocean View in Wailea! WE204
Welcome to Wailea Ekolu Village, unit 204! This is a top floor, FRONT LINE, two bed, two bath condo with a 180 degree ocean view! Overlooking the Wailea Blue Golf Course course, this unit boasts dramatic ocean views! The interior has been extensively remodeled and...