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 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...
Wailea Ekahi Gem! Remodeled Large 1BR+sleeper, Close to Beach & Pools, XL Lanai
Experience Maui paradise at Wailea Ekahi 21B, a fully renovated ground-floor one-bedroom/two-bath vacation condo nestled within the prestigious Wailea resort district. This beautiful unit showcases a designer remodel, offering a spacious, modern, and bright atmosphere...
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...
130K Hawaiian Reno on Wailea Blue Golf *Ocean View
BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of...
Spectacular Ocean Views! 5 Star Reviews! ʻIke Kai at Wailea Ekolu Village
Aloha!Welcome to our Our Maui Condo! ʻIKE KAI, which means "OCEAN VIEWS," offers a one-bedroom, two-bath, ground floor retreat that will delight even the most discerning traveler. Nestled in the desirable lower section of the Wailea Ekolu Village complex, our condo...
Wailea Elua Village 107 - 2 Bedroom Ocean View Condo
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...
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.
Luxury Condo in Wailea with sweeping views
2 large master ensuite bedrooms with Cal King beds. Sweeping views of Kaho'olawe, Molokini, and Lanai islands and spectacular sunsets. Beaches, restaurants, and Shops of Wailea all within walking distance. Fully equipped kitchen, with plenty of dining wear and cooking...
Only Steps to Ulua Beach and the main Wailea Ekahi Pool/Pavilion -1 Bd+2Ba
New A/C system, new bed and mattress, new furniture, new electronics. Professional Photos Pending - Wailea Rentals presents: Wailea Ekahi Village 8E - Ekahi means #1 in Hawaiian and that is exactly what Ekahi Village is - 1 of Wailea's top luxury beachfront condominium...
Wailea Grand Champions 183 - 2 Bedroom Garden View Condo
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...
Newly remodeled corner unit w/ large patio -Wailea Treasure awaits you!
In sunny Wailea, a short stroll to some of south Maui's most incredible sand beaches, you will find our WAILEA TREASURE! Close proximity to all of the great Wailea amenities like world class resorts, golf, tennis and shopping. We offer a recently remodeled (down to the...
Wailea Elua Village 1102 - 1 Bedroom Ocean View Condo
This ocean view one-bedroom Wailea Elua Village condo is a great home base for experiencing the joys and beauty of south Maui. Easily walk down to the white-sand Ulua Beach that fronts this property. Be one of the first in the ocean in the morning to snorkel the...
New Listing! - Wailea Ekahi 39E - Luxurious Ocean View Condo, Split AC!
Welcome to Wailea Ekahi 39E, a beautifully appointed one-bedroom, two-bath condo offering breathtaking ocean views and the perfect blend of comfort, style, and convenience. Whether you're planning a romantic retreat, a peaceful solo vacation, or a productive remote work...
Wailea Grand Champions 31 - 2 Bedroom Golf Course View Condo
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...
1BEDROOM/2BATH Downstairs Condo in Wailea Ekahi Village #46A -- Locally Owned
Retreat and relax in this comfortable, serene, light and airy, completely remodeled unit. This ground floor unit in the quiet, beachfront Wailea Ekahi Village won't ask you to carry your bags up a single step, while still providing a private and open environment....
Wailea Grand Champions 43 - 2 Bedroom Garden View Condo
Wailea Grand Champions 43 is a stunning vacation rental nestled in the heart of Wailea, offering a luxurious escape with breathtaking views and unparalleled comfort. This elegantly designed property is ideal for those seeking both relaxation and adventure on the...
Wailea Ekahi Village 10F - 1 Bedroom Garden View Condo
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...
Wailea Grand Champions 71 - 2 Bedroom Golf Course & Partial Ocean View
Wailea Grand Champions 71 is a beautifully updated ground-floor vacation rental that offers both fairway and ocean views from the living room and private lanai. This spacious two-bedroom, two-bath condo comfortably accommodates up to six guests, providing ample room for...
Wailea Grand Champions 73 - 1 Bedroom Partial Ocean View Condo
Wailea Grand Champions Villa 73 is a recently renovated vacation rental that offers a perfect blend of luxury, comfort, and stunning views in the heart of Wailea, Maui. As you enter the villa, you\'re greeted by a bright and spacious great room, ideal for relaxation...
Wailea Elua Village 1203 - 1 Bedroom Oceanfront Condo
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...
Wailea Grand Champions 84 - 3 Bedroom Golf Course & Partial Ocean View Condo
Wailea Grand Champions 84 is a beautifully appointed vacation rental located in the prestigious Wailea area of Maui. This spacious three-bedroom, two-bathroom condo offers views out over the Wailea Blue Golf Course as well as a partial ocean view. It\'s size and...
Fully Remodeled Elegance in Wailea 2Bed 2Bath
Welcome to The Palms at Wailea, where we offer you exceptional experiences in a variety of realms that exceed your expectations. Nestled within the prestigious Wailea town, our villa complex exudes charm, luxury, and allure.Nestled within the exclusive town of Wailea,...
Wailea Ekahi Village 11C - 2 Bedroom Garden View Condo
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...
Wailea Ekahi 24C, Paradise in Style! Spacious 2 Bedroom 2 Bathroom, SLEEPS 6.
Welcome to Codge’s Beach House! This 2 bedroom , 2 bathroom unit (SLEEPS 6), was remodeled in late 2022 with ceiling fans, new split ductless AC's, brand new kitchen and bathroom and with a lot of thought for comfort and ease of use. We are on the second floor with 3...
Wailea Elua Village 1301 - 1 Bedroom Oceanfront Condo
Experience the ultimate Hawaiian getaway when vacationing at Wailea Elua 1301. This beautifully designed vacation rental featuring an open floor plan showcases spectacular ocean views from the living room, dining area, and kitchen. The great room is perfect for...
Wailea Grand Champions 95 - 3 Bedroom Golf Course View Condo
Do your Maui vacation right! Wailea Grand Champions 95 is surrounded by tropical landscaping and rolling green fairways, that serve as a constant reminder that you are vacatioing in paradise. This vacation rental offers a perfect blend of comfort and luxury, making it...
FULL OCEAN VIEW WAILEA
Bright airy updated large 1 bedroom 2 bath top floor in sought- after Wailea Ekahi Village. 27D is a top corner unit known for our panoramic ocean views. Enjoy a Mai Tai while gazing out at the whales breaching out of the ocean at sunset! This unit boats high ceilings,...
Wailea Beach Villas D302 - 3 Bedroom Ocean View Villa
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...
PICTURESQUE OCEAN VIEW CONDO - LAST MINUTE DEAL! BEAUTIFUL WAILEA AT ELUA 2002
Wailea Elua #2002 Ocean View CondoThis newly remodeled in 2021 second floor 2 bedroom and 2 bathroom condo has an open floor plan, large lanai that looks out to the Ocean. Complimentary high-speed internet is included.Elua Village is a premier destination resort, with 2...
Wailea Grand Champions 97 - 1 Bedroom Golf Course View Condo
Wailea Grand Champions 97 is a premier vacation rental located in the serene tourist retreat of Wailea. This exquisite property combines elegant design with modern amenities to provide a truly exceptional getaway experience. Upon arrival at Wailea Grand Champions 97,...
Tropical Wailea Retreat
We invite you to come and stay at our spacious suite where you can enjoy the exclusive Wailea lifestyle. Relax & restore in this serene space surrounded by tropical palms!This bright and airy 1 bed/2 bath, corner end unit is a modern Hawaiian retreat. The suite features...
Wailea Beach Villas E202 - 3 Bedroom Garden View Villa
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...
Cozy Treasure Nestled on a Lush Oceanfront Property - Wailea Elua 1508
Wailea Elua #1508 – Partial Ocean Views & Comfort Near PoolSet within the prestigious Wailea Elua Village, Wailea Elua #1508 offers an ideal balance of peaceful luxury and island convenience. This spacious 2-bedroom, 2-bathroom condo features partial ocean views, a...
Luxurious Wailea Ocean Vistas
Summary:Completely remodeled (Dec 2022). Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful...
4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach
Discover the breathtaking Wailea area in Kihei and indulge in top-notch tropical life at this lavish four-bedroom holiday house. Nestled just minutes away from the pristine Wailea Beach and the vibrant Shops at Wailea, this property offers the perfect blend of...
Wailea Beach Villas F201 - 3 Bedroom Ocean View Villa
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,...
The Best Condo in Wailea Ekahi Village!
Wailea Ekahi Village is a tropical oasis that sits right on Ke'awakapu Beach, considered by locals to be Maui’s best beach. Surrounded by major resort hotels, shopping centers, and championship golf courses, it's a vacationer's dream! This condo is in one of Ekahi...
Stunning Ocean View Wailea Beach Villa- Book & Save
Most popular Maui Condo Wailea Beach Villa L409 Rated Perfect . 4BR (3 Kings/1 Queen, or 2 Kings/ 2 Twins/1 Queen) 3 BA villa . Spectacular panoramic ocean view. This elegant 4th Floor Villa is nestled between The Grand Wailea & The Shops at Wailea. Almost 3000' with...
Wailea Ekahi 54C: Best View & New Kitchen
Our Family owns 2 - Two bedroom units above and below each other in Ekahi Village. This is perfect for large Family vacations or groups of friends traveling together. Be together, but still enjoy your own comfortable bedroom and bathroom. VIEWS: Ocean views from nearly...
Wailea Point | 3203 - 2 Bedroom Ocean View Condo - 30+ Night Luxury Stays
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...
Wailea Oasis: Relax in Your Spacious Villa w/ Lush Tropical Views, Private Lanai
Grand Champions is perfectly situated in Wailea, in spectacular South Maui. World-class beaches, golf, restaurants, and two swimming pools await your visit. Two master suites with king-size beds plus one queen-size sleeper sofa, air conditioning throughout, tastefully...
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...
Luxury Wailea Family Condo. NEW EVERYTHING! Complete Remodel! AC and Pool.
If you are looking for a modern, luxurious retreat for families in Wailea with BRAND NEW EVERYTHING, look no further! This unit was completely renovated. Guests can enjoy:— Modern, deluxe kitchen with all new appliances. Fully stocked with everything you need to cook...
Wailea Ekahi 1B Recently Remodeled Ocean View 1st Floor Luxury 1BD 2BA Condo
Unit 1B is located on beautiful Keawakapu Beach in gorgeous Wailea. This totally remodeled lower village, ground floor unit has one large lanai with a beautiful ocean view and Ekahi’s 34 acre tropical landscaped gardens. It has a lanai table that seats 6. It is...
Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, Maui
Introducing: Wailea Elua 1308. Offering a front row beachfront location, this immaculately maintained unit features unobstructed ocean view corridors, privacy, convenient access to the Wailea Beach Path, and one of the world’s best beaches as the front yard....
Wailea Beach Villas G302 - 3 Bedroom Ocean View Villa
Welcome to Villa G302, your luxurious Hawaiian escape where relaxation meets elegance. This stunning ocean view villa features two walls of retractable sliding doors that seamlessly blend the open living area with a spacious corner lanai, complete with a built-in Viking...
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all
Hyundai Santa Fe with room for five is made available to guests through Turo for $40-$60 a day. If you are interested, let us know.DIRECT TO ROOM CHECK-IN: At 1206 The Palms, you go directly to your private condo without ever needing to check in. The same is true upon...
Luxe Oceanview Hideaway on Wailea Old Blue Golf Course
WAILEA PARADISE HIDEAWAYEscape to a serene and elegant retreat in the heart of Wailea.Set on the renowned Wailea Old Blue Golf Course, this ocean-view villa blends luxury with convenience—just minutes from the beach, the Shops at Wailea, fine dining, and world-class...
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Our Eco Friendly home is conveniently located near Maui’s most beautiful beaches. Minutes away from Wailea Beach, Keawakapu Beach, Kamaole Beach III and the famous Big Beach. Also, sitting at the base of Haleakala you will have opportunities to adventure to incredible...
Steps to Beach. Stunning View. Lovely 2BR Condo near Wailea
Enjoy paradise at one of Maui's premier beaches. Our air-conditioned retreat features a clean and bright interior, offering stunning views from the main living area. Enjoy cooking in a well-equipped kitchen and relax with beach chairs, umbrellas, and boogie boards...