Wailea Vacation Rentals

Wailea is a luxury resort area in South Maui featuring upscale vacation rentals including oceanview condos and villas near top beaches, golf, shopping, and fine dining.

Browse Wailea Vacation Rentals by condo/hotel name:

Ekahi Village

Wailea Grand Champions

Wailea Point

Wailea is one of Maui's most sought-after destinations, known for its upscale resorts, golden beaches, and beautifully maintained landscapes. Vacation rentals in Wailea include oceanview condos, luxury villas, and spacious townhomes - ideal for couples, families, and groups seeking a refined island getaway. With sunny weather year-round and direct access to world-class beaches like Wailea Beach, Polo Beach, and Ulua Bay, Wailea is perfect for both relaxation and outdoor adventure.

In addition to its scenic beauty, Wailea is home to championship golf courses, luxury spas, high-end shopping at The Shops at Wailea, and a variety of oceanfront dining options. Whether you're watching the sunset from your lanai or heading out for a paddleboarding session, Wailea offers the perfect balance of serenity and sophistication. Browse our Wailea vacation rentals below and find the perfect home base for your South Maui escape.

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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 down to the beach to catch sunset.

2 bedroom
2 bathroom
Sleeps 6

from $680

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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 help keep this condo cool year round.

1 bedroom
1 bathroom
Sleeps 4

from $487

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Spectacular Ocean Views! 5 Star Reviews! ʻIke Kai at Wailea Ekolu Village

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 features updated finishes, including new floors, kitchen appliances and updated bathrooms.

1 bedroom
2 bathroom
Sleeps 4

from $438

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$Only Steps to Ulua Beach and the main Wailea Ekahi Pool\/Pavilion -1 Bd+2Ba$

Only Steps to Ulua Beach and the main Wailea Ekahi Pool/Pavilion -1 Bd+2Ba

Recently upgraded furniture - 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 resorts. Located directly on Keawakapu Beach at the north end of Wailea on Maui's quiet, sunny, south side, Wailea Ekahi features 33 acres of beautiful, mature landscaped grounds in a low-rise, low-density village setting stretching from the beachfront pool up to Wailea Alanui Drive.

1 bedroom
2 bathroom
Sleeps 4

from $519

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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.

1 bedroom
1 bathroom
Sleeps 4

from $633

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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.

1 bedroom
2 bathroom
Sleeps 4

from $797

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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.

1 bedroom
2 bathroom
Sleeps 4

from $592

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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 lifestyle while vacationing on Maui.

1 bedroom
1 bathroom
Sleeps 4

from $496

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'Best Vacation Ever' Say Our Guests! Special May Rates

'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 standards.

2 bedroom
2 bathroom
Sleeps 6

from $442

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Luxury at its Best with Big Ocean Views!!

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 lighting & quiet remote controlled air conditioning.

2 bedroom
2 bathroom
Sleeps 4

from $589

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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 – this vacation residence utilizes an indoor-outdoor lifestyle with a great room and kitchen that open up to a spacious covered private lanai.

1 bedroom
2 bathroom
Sleeps 4

from $496

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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 ocean views.

2 bedroom
2 bathroom
Sleeps 6

from $1,643

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Polo Beach 808! Unique opportunity one-bedroom, top floor home.

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, Kaho'olawe, and looking back at South Maui.

1 bedroom
2 bathroom
Sleeps 2

from $647

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Fully Remodeled Elegance in Wailea 2Bed 2Bath

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, this condo boasts two bedrooms, two bathrooms, and a new queen-size sofa pull-out.

2 bedroom
2 bathroom
Sleeps 6

from $498

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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 and family.

2 bedroom
2 bathroom
Sleeps 6

from $861

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FULL OCEAN VIEW WAILEA

Full renovation of this condo was completed December 2020. Both bathrooms, master bedroom, as well as entire condo painted and replacement of baseboards and door trims throughout.

Bright airy updated large 1 bedroom 2 bath top floor in sought- after Wailea Ekahi Village.

1 bedroom
2 bathroom
Sleeps 3

from $585

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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 for additional endless entertainment and relaxation.

2 bedroom
2 bathroom
Sleeps 6

from $1,325

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Wailea Hoolei 93-3 Rarely Priced for Last Minute May Getaway at Luxurious Condo

Wailea Hoolei 93-3 Rarely Priced for Last Minute May Getaway at Luxurious Condo

The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.
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.

3 bedroom
3 bathroom
Sleeps 8

from $1,303

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Enjoy garden views and ocean glimpses from your private lanai at #138

Enjoy garden views and ocean glimpses from your private lanai at #138

Location! Location! Location! 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 relax on your own private lanai and take in wonderful garden views and peek-a-boo views of the ocean.

2 bedroom
2 bathroom
Sleeps 6

from $473

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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 lanai.

1 bedroom
2 bathroom
Sleeps 4

from $582

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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 state-of-the-art appliances, ensuring a luxuriously modern stay for guests.

2 bedroom
2 bathroom
Sleeps 5

from $480

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Luxury Wailea Family Condo. NEW EVERYTHING! Complete Remodel! AC and Pool.

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 in the Summer of 2021. Guests can enjoy:

— Modern, deluxe kitchen with all new appliances.

2 bedroom
2 bathroom
Sleeps 6

from $490

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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 beautiful island of Maui.

2 bedroom
2 bathroom
Sleeps 6

from $479

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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.

2 bedroom
2 bathroom
Sleeps 6

from $702

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Exquisite Oceanview Villa with Resort Amenities in Gated Community

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 private lanai!

3 bedroom
3 bathroom
Sleeps 8

from $1,600

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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 relaxation and enjoyment for the whole family.

2 bedroom
2 bathroom
Sleeps 6

from $475

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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 tropical furnishings that create a warm and inviting atmosphere.

2 bedroom
2 bathroom
Sleeps 6

from $1,065

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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 with a wide hallway leading past both bedrooms toward the great room where a generous living room features a large, flat screen TV and plush furnishings.

2 bedroom
2 bathroom
Sleeps 6

from $1,598

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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 after a day of golfing or beach activities.

1 bedroom
2 bathroom
Sleeps 4

from $430

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Wailea, Oceanfront, Polo Beach Club Condo #403

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 Big Beach.

2 bedroom
2 bathroom
Sleeps 5

from $885

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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 locations.

1 bedroom
1 bathroom
Sleeps 4

from $492

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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 an ideal choice for families or groups seeking a memorable getaway in Maui.

3 bedroom
2 bathroom
Sleeps 6

from $604

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Gorgeous Wailea Elua 2Bd+2Ba 1st Floor, Ocean View Paradise Condominium #2301

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 demand with a King-sized bed in the primary bedroom and two single beds in the guest bedroom which can be converted into a 'king' sized bed upon request, and a Queen-sized sofa bed.

2 bedroom
2 bathroom
Sleeps 6

from $1,000

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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 book, enjoying a meal al fresco at the covered dining table, or savoring a cocktail with a front row seat for a prismatic sunset.

2 bedroom
2 bathroom
Sleeps 4

from $1,245

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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 comfortably accommodates families or groups of up to 6 guests.

3 bedroom
3 bathroom
Sleeps 8

from $2,380

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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 surf.

1 bedroom
2 bathroom
Sleeps 2

from $739

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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, guests are welcomed by a sophisticated and stylish interior that exudes comfort and charm.

1 bedroom
2 bathroom
Sleeps 4

from $427

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Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4

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.
5 bathrooms, a large living room, fully equipped kitchen (Mr.

3 bedroom
3 bathroom
Sleeps 8

from $1,524

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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.

2 bedroom
2 bathroom
Sleeps 6

from $1,485

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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 a unique island atmosphere.

1 bedroom
2 bathroom
Sleeps 4

from $435

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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 bedroom is furnished with two twin-sized beds, ensuring ample sleeping arrangements.

2 bedroom
2 bathroom
Sleeps 6

from $474

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Makena Surf | B205 | Beachfront Resort

Makena Surf B205 is an exquisite oceanfront vacation rental located within the luxurious Makena Surf resort, nestled on the stunning Po'olenalena Beach in Maui. This beautifully appointed second-floor residence offers a serene escape, perfect for families or couples seeking relaxation and privacy in a tropical paradise.

2 bedroom
2 bathroom
Sleeps 4

from $922

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Beautiful Sunsets with this Ocean View Condo! Mar 23 - April 7 Open!

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 the West Maui Mountains, and the island of Lanai while enjoying your morning coffee or evening cocktails.

2 bedroom
2 bathroom
Sleeps 4

from $358

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Wailea Grand Champions | 121

Wailea Grand Champions 121 is ground-floor vacation bliss. Enjoy the easy convenience of transporting beach equipment, groceries, golf clubs, and vacation souvenirs from your rental car to your vacation rental. Designed with comfort in mind, the tiled and wood flooring, ceiling fans, air conditioning, and louvered windows throughout this condo maintain a cool and pleasant environment.

1 bedroom
2 bathroom
Sleeps 4

from $435

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Elua 1603: Premier Views, Exquisite Updates!

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.

2 bedroom
2 bathroom
Sleeps 4

from $1,437

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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 elevator, ensuring privacy and exclusivity.

3 bedroom
3 bathroom
Sleeps 8

from $1,863

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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 beauty and vibrant colors.

1 bedroom
2 bathroom
Sleeps 4

from $426

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$Fantastic unit! 10\/10! Hear the waves from the lanai! 1 bedroom unit. Sleeps 4$

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 waterfront pavilion at Ekahi Village.

1 bedroom
1 bathroom
Sleeps 4

from $446

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Luxurious Ho'olei Villa with Ocean Views, Two Story Townouse!

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!

3 bedroom
3 bathroom
Sleeps 6

from $1,931

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Tiki Tiki - A Gorgeous Boho Beach Hideaway!

Tiki Tiki - A Gorgeous Boho Beach Hideaway!

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 of Wailea.

1 bedroom
1 bathroom
Sleeps 2

from $495

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