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 Ekahi Village | 22F
Wailea Ekahi 22F is located in an ideal location, closest on property (a short walk) to Keawakapu Beach and the Wailea Ekahi beachfront swimming pool and recently remodeled beach pavilion. Whip up some happy hour drinks and snacks in your vacation rental and then stroll...
Wailea Ekahi Village | 25D
Welcome to Wailea Ekahi 25D, an exquisite vacation rental that embodies the essence of luxurious island living in Wailea. This one-bedroom, one-bathroom second-floor condo offers a enjoys elevated views of the 32-acre manicured grounds. Vaulted ceiling and tiled floors...
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...
Only Steps to Ulua Beach and the main Wailea Ekahi Pool/Pavilion -1 Bd+2Ba
Recently upgraded furniture - Professional photos pendingWailea 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 resorts. Located directly on Keawakapu...
Wailea Ekahi Village | 29D
This Wailea Ekahi Village residence completed a beautiful renovation in 2022. From colorful artwork to comfortable and sleek furnishings, you will instantly recognize why this Wailea vacation rental earned our highest internal ranking of ''platinum'' status.This private...
Ocean View, Steps away from the pool
"COVID-19: Dear travelers. Even though we have always maintained an exceptionally clean property, you can rest assured that we are following the guidelines of the CDC and Expedia/VRBO for enhanced cleaning and disinfecting of short term rentals. Additionally, the State...
Wailea Ekahi Village | 34E
Wailea Ekahi 34E is a charming second-floor suite that offers breathtaking ocean views of Molokini and Kaho'olawe. You may find yourself spending extended time on your private and spacious lanai perfect for soaking in the picturesque scenery.This Wailea vacation rental...
Wailea Ekahi Village | 35C
Wailea Ekahi 35C is a stunning vacation rental located in the desirable Wailea community. This beautifully appointed one-bedroom, one-bathroom condo offers an ideal blend of comfort and luxury. Make use of the ground floor location to really live an indoor/outdoor...
'Best Vacation Ever' Say Our Guests! Special May Rates
You will love this luxurious, air conditioned, two bedroom, two bath, 1300 square foot Villa! Fully furnished, with its own spacious, private dining lanai, this unit was completely remodeled in 2020. It is immaculate, impeccably maintained and cleaned to the highest...
Luxury at its Best with Big Ocean Views!!
Aloha & welcome to the Wailea Diamond Suite at Ekolu Village #305!The moment you step through the door you’ll know you’ve come home to luxury in this elegant 2 bedroom, 2 bath condo. Each bedroom features its own unique bath, private lanai sanctuary, ambient...
Wailea Ekahi Village | 42C
This 1,090 square foot one-bedroom, two bathroom vacation rental sleeps four comfortably. Wailea Ekahi Village 42C is conveniently located close to the pool, but offers a quiet sanctuary surrounded by lush greenery. Featuring contemporary, yet comfortable décor –...
Makena Surf | C105 | Beachfront Resort
Enter the cool marbled foyer of Makena Surf C105, a luxurious 1,600 sq. ft. ocean view vacation rental on the first floor of the prestigious Makena Surf resort. As you make your way to the elegant living area, you'll be greeted by sliding doors that showcase spectacular...
Polo Beach 808! Unique opportunity one-bedroom, top floor home.
Unique opportunity to stay in a one-bedroom, top floor home at one of the most desired properties on Maui. Polo Beach #808 will be your favorite place to stay when visiting the island. Top floor, corner unit with EXQUISITE VIEWS of the Pacific Ocean, Molokini,...
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,...
Polo Beach Club | 301
Welcome to Polo Beach Club 301, a stunning third-floor corner residence that offers breathtaking views of Polo Beach. This spacious unit exemplifies the indoor-outdoor lifestyle that Hawaii is famous for, making it perfect for both entertaining and relaxing with friends...
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 | PH111
Curated with our guests in mind, Wailea Beach Villas PH111's outdoor elements are just as immaculate as the home’s interiors. Unwind and enjoy peekaboo views of the ocean along with tropical greenery from your private lanai. The pristine Wailea Beach is located nearby...
Enjoy garden views and ocean glimpses from your private lanai at #138
Location! Location! Location! Who needs a car?!? This central Wailea location makes it favorable as you can find tennis, golf, retailers at the Shops at Wailea, casual to fine dining restaurants, world's top beaches, and five-star hotels just moments away.Kick back and...
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 Village | 54D
Wailea Ekahi 54D is a stunning second-floor vacation rental offering breathtaking views of the ocean and West Maui mountains. This one-bedroom, two-bathroom condo boasts panoramic vistas from multiple vantage points, including the living room, kitchen, and primary...
Wailea Grand Champions | 31
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...
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 Grand Champions | 43
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 | 38F
Nestled in the heart of Wailea, Wailea Ekahi 38F is an exquisite vacation rental that offers a luxurious and serene Maui escape. This stunning two-bedroom, two-bathroom condo takes full advantage of its second floor positioning and boasts panoramic ocean views. Take...
Exquisite Oceanview Villa with Resort Amenities in Gated Community
This property is hotel zoned, and not being affected by the recent proposed legislation.Located in highly desirable secluded area of neighborhood your villa welcomes you with spacious floor plan and sweeping ocean views. Marvel at the beautiful Maui sunsets from your...
Wailea Grand Champions | 71
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...
Makena Surf | B106 | Beachfront Resort
Welcome to Makena Surf B106, a stunning two-bedroom beachfront suite just steps away from the golden sands and the ocean's edge. This beautifully appointed residence combines luxury and comfort, featuring elegant tray ceilings, exquisite wood cabinetry, and contemporary...
Wailea Beach Villas | PH410
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 Kaho’olawe, Molokini and Lana'i.From your private elevator landing, the suite opens...
Wailea Elua Village | 804
The Wailea Elua 804 vacation rental is a true gem nestled within the picturesque Wailea resort community on the island of Maui. From the moment you step inside this stunning, 1,700-square-foot condo, you're enveloped in a sense of luxury and tranquility. The...
Wailea Grand Champions | 73
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 | 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...
Wailea, Oceanfront, Polo Beach Club Condo #403
Location, location, location…. Polo Beach is the premiere condominium that sits at the south end of the Wailea Beach walk, next to the Fairmont Kei Lani resort. Our unit is on the sunny south side of the building, overlooking the pool area and ocean, and south towards...
Wailea Ekahi Village | 39A
If you’re seeking privacy and relaxation, Wailea Ekahi Village 39A offers a secluded Maui retreat nestled behind a lush row of towering tropical plants. This hidden gem provides a tranquil oasis perfect for unwinding after a full day exploring Maui's scenic...
Wailea Grand Champions | 95
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...
Gorgeous Wailea Elua 2Bd+2Ba 1st Floor, Ocean View Paradise Condominium #2301
New living room furniture and lanai furniture - Absolutely Lovely! Wailea Elua Village #2301 is a premier vacation condominium located in Elua Village which is directly on the sugar sand of Ulua beach in Wailea. This impressive vacation condominium is constantly in high...
Wailea Elua Village | 1001
Wailea Elua Village #1001 is a stunning oceanfront sanctuary that has recently undergone a complete transformation. For discerning travelers who enjoy the best of Wailea, the extended outdoor living space allows you to enjoy panoramic ocean views while relaxing with a...
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...
Wailea Elua Village | 1203
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 | 97
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,...
Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4
Newly Remodeled in 2023! Come relax and enjoy the spectacular ocean and island views in this rare three bedroom condo perched on the very top row fourth tier in the Ho’olei community.This spacious unit has 3 bedrooms, 3.5 bathrooms, a large living room, fully equipped...
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....
Wailea Grand Champions | 104
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...
Wailea Grand Champions | 111
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...
Beautiful Sunsets with this Ocean View Condo! Mar 23 - April 7 Open!
This beautiful top floor, Grand Champs condo has one of the best ocean views in the complex. This fully updated 2 bedroom, 2 full bath condo has wonderful panoramic ocean views perfect for sunsets and whale watching. From the extra large, newly tiled lanai, you can see...
Elua 1603: Premier Views, Exquisite Updates!
Wailea Elua Village #1603 boasts some of the best Ocean Views and is located on one of the most prestigious properties on Maui. This condo has been lovingly maintained and updated to ensure it remains a luxury-level choice for those traveling to Maui.Featuring the...
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 Grand Champions | 152
Relax on your private lanai at Grand Champions #152, perched upon the second-floor, and enjoy views of manicured fairways, putting greens, and tee boxes as golfers tackle the Wailea Golf Course. This vacation rental is ideally situated to showcase Maui’s natural...
Fantastic unit! 10/10! Hear the waves from the lanai! 1 bedroom unit. Sleeps 4
This one bedroom, smoke-free condo, is located in Ekahi Village, and is a short (less than 4 minutes) relatively flat walk to the beautiful Keawakapu Beach. The unit is located in the lower village. You can stay on the beach for the day or enjoy the amazing new...
Luxurious Ho'olei Villa with Ocean Views, Two Story Townouse!
Stay longer, enjoy more! Book 10+ nights and receive a free mid-stay clean. Book 14+ nights and get one night free!This property is hotel zoned, and not being affected by the recent proposed legislation.Welcome to this luxurious Ho'olei Villa with amazing ocean views!...
Wailea Grand Champions | 159
Wailea Grand Champions 159 is a beautifully updated three-bedroom vacation rental located along the fairway of the Wailea Blue Golf Course. This ground-floor condo offers a spacious layout with three bedrooms and two bathrooms, making it ideal for families or groups...