Wailea Vacation Rentals

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.

Browse Wailea Vacation Rentals by condo/hotel name:

Ekahi Village
Elua Village
Hoolei
Mana Kai
Polo Beach Club
The Palms at Wailea
Wailea Beach Villas
Wailea Ekahi
Wailea Ekolu
Wailea Grand Champions
Wailea Point
List
Map
Wailea Ekahi 22F Ocean View Condo Near Beach
Wailea Ekahi 22F Ocean View Condo Near Beach
Wailea Ekahi 22F Ocean View Condo Near Beach

Wailea Ekahi 22F Ocean View Condo Near Beach

Experience the ultimate Maui vacation at Wailea Ekahi 22F, a stunning second-floor condo offering sweeping ocean views and modern comforts. Located just a short walk from Keawakapu Beach, this beautifully remodeled two-bedroom residence provides a perfect blend of privacy, comfort, and convenience.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $680 
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Wailea Ekahi 25D Luxury Island Condo
Wailea Ekahi 25D Luxury Island Condo
Wailea Ekahi 25D Luxury Island Condo

Wailea Ekahi 25D Luxury Island Condo

Welcome to Wailea Ekahi 25D, a beautifully appointed condo that captures the essence of upscale island living in Wailea. This second-floor, one-bedroom, one-bathroom residence offers a perfect blend of comfort, style, and stunning views of lush, manicured grounds.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Wailea
from $487 
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Beautiful Ocean View Condo in Wailea Ekolu Village
Beautiful Ocean View Condo in Wailea Ekolu Village
Beautiful Ocean View Condo in Wailea Ekolu Village

Beautiful Ocean View Condo in Wailea Ekolu Village

Aloha! Welcome to our Maui condo, �IKE KAI, meaning "OCEAN VIEWS," offering a comfortable one-bedroom, two-bath retreat in Wailea Ekolu Village. Nestled on the ground floor of Building #7, this updated unit boasts new floors, modern kitchen appliances, and renovated bathrooms, providing a seamless blend of comfort and style.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $438 
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Wailea Ekahi Village 8E Beachfront Condo Maui
Wailea Ekahi Village 8E Beachfront Condo Maui
Wailea Ekahi Village 8E Beachfront Condo Maui

Wailea Ekahi Village 8E Beachfront Condo Maui

Experience the perfect Maui getaway at Wailea Ekahi Village 8E, a premier beachfront condominium nestled on Keawakapu Beach. This condo offers a luxurious, low-density resort setting with 33 acres of lush, mature landscaping, providing an oasis of tranquility and natural beauty.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $519 
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Wailea Ekahi Village Ocean View Condo with Pool
Wailea Ekahi Village Ocean View Condo with Pool
Wailea Ekahi Village Ocean View Condo with Pool

Wailea Ekahi Village Ocean View Condo with Pool

This beautifully renovated Wailea Ekahi Village residence offers a luxurious and comfortable tropical retreat on Maui. Completed in 2022, the condo features vibrant artwork, sleek furnishings, and a prime location with stunning ocean views from the living room, kitchen, and outdoor lanai.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Wailea
from $633 
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Renovated Maui Beachfront Condo with Pool & Sunset Views
Renovated Maui Beachfront Condo with Pool & Sunset Views
Renovated Maui Beachfront Condo with Pool & Sunset Views

Renovated Maui Beachfront Condo with Pool & Sunset Views

Welcome to your perfect Maui getaway in this beautifully renovated beachfront condo, just two years new. The modern, fresh design creates a comfortable and inviting atmosphere for your stay. Located on the ground floor, the unit offers easy access from the parking lot, making unloading and coming and going effortless.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $797 
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Wailea Ekahi 34E Ocean View Condo Maui
Wailea Ekahi 34E Ocean View Condo Maui
Wailea Ekahi 34E Ocean View Condo Maui

Wailea Ekahi 34E Ocean View Condo Maui

Experience the beauty of Maui from Wailea Ekahi 34E, a delightful second-floor condo featuring breathtaking views of Molokini and Kaho'olawe. The spacious lanai is perfect for relaxing while soaking in the island scenery, making it an ideal retreat after exploring Maui’s outdoor adventures.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $592 
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Wailea Ekahi 35C Luxury Maui Condo with Pool
Wailea Ekahi 35C Luxury Maui Condo with Pool
Wailea Ekahi 35C Luxury Maui Condo with Pool

Wailea Ekahi 35C Luxury Maui Condo with Pool

Immerse yourself in the beauty of Maui with this stunning ground-floor one-bedroom condo at Wailea Ekahi 35C. Set within the desirable Wailea community, this beautifully appointed residence offers a perfect blend of comfort and luxury for your island getaway.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Wailea
from $496 
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Luxurious 2BR Villa in Wailea near Beaches
Luxurious 2BR Villa in Wailea near Beaches
Luxurious 2BR Villa in Wailea near Beaches

Luxurious 2BR Villa in Wailea near Beaches

Experience the ultimate Maui retreat in this luxurious, air-conditioned two-bedroom, two-bath villa spanning 1300 square feet. Fully furnished and meticulously maintained, this spacious condo was completely remodeled in 2020, offering a blend of modern comfort and tropical elegance.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $442 
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Luxury Wailea Diamond Suite at Ekolu Village
Luxury Wailea Diamond Suite at Ekolu Village
Luxury Wailea Diamond Suite at Ekolu Village

Luxury Wailea Diamond Suite at Ekolu Village

Welcome to the Wailea Diamond Suite at Ekolu Village #305, your luxurious Hawaiian retreat. Step inside this beautifully appointed 2-bedroom, 2-bath condo where every detail exudes comfort and elegance. Each bedroom boasts its own private bath, creating a perfect sanctuary for relaxation.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $589 
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Wailea Ekahi Village 42C Luxury Maui Condo
Wailea Ekahi Village 42C Luxury Maui Condo
Wailea Ekahi Village 42C Luxury Maui Condo

Wailea Ekahi Village 42C Luxury Maui Condo

The 1,090 sq ft Wailea Ekahi Village 42C offers a perfect blend of comfort and natural beauty, ideal for a family or couple seeking a relaxing Maui escape. This spacious one-bedroom, two-bathroom condo comfortably accommodates four guests, featuring a serene garden view and a prime location close to the pool and lush greenery.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $496 
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Luxury Ocean View Makena Surf C105 Rental
Luxury Ocean View Makena Surf C105 Rental
Luxury Ocean View Makena Surf C105 Rental

Luxury Ocean View Makena Surf C105 Rental

Enter the elegant marbled foyer of Makena Surf C105, a luxurious 1,600 sq. ft. first-floor ocean view condo located in the prestigious Makena Surf resort. As you step inside, sliding glass doors reveal spectacular views of the Pacific Ocean, setting the tone for your memorable stay.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,643 
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Elegant Top Floor Maui Condo with Ocean Views
Elegant Top Floor Maui Condo with Ocean Views
Elegant Top Floor Maui Condo with Ocean Views

Elegant Top Floor Maui Condo with Ocean Views

Experience the ultimate Maui getaway in this exquisite top-floor one-bedroom condo at Polo Beach Club in Wailea. Boasting breathtaking views of the Pacific Ocean, Molokini, and Kaho'olawe, this corner unit offers a private, west-facing lanai perfect for sunset viewing.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 2
Hawaii> Wailea
from $647 
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Wailea Palm Villa Maui Luxury Vacation Condo
Wailea Palm Villa Maui Luxury Vacation Condo
Wailea Palm Villa Maui Luxury Vacation Condo

Wailea Palm Villa Maui Luxury Vacation Condo

Welcome to The Palms at Wailea, offering exceptional experiences in a charming, luxurious setting. Located in the prestigious town of Wailea, this beautifully renovated condo blends island-inspired and contemporary decor for a truly inviting atmosphere.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $498 
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Luxury Oceanfront Condo at Polo Beach Club
Luxury Oceanfront Condo at Polo Beach Club
Luxury Oceanfront Condo at Polo Beach Club

Luxury Oceanfront Condo at Polo Beach Club

Welcome to Polo Beach Club 301, a beautiful third-floor corner residence offering spectacular views of Polo Beach. This spacious condo embodies the Hawaii indoor-outdoor lifestyle, ideal for both entertaining and relaxing with loved ones.
Inside, the open-concept great room seamlessly connects to a fully-equipped kitchen featuring a center island with bar seating for four, high-end appliances, wine and beverage refrigerators, and a full-size refrigerator.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $861 
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Bright Ocean View Condo in Wailea Ekahi Village
Bright Ocean View Condo in Wailea Ekahi Village
Bright Ocean View Condo in Wailea Ekahi Village

Bright Ocean View Condo in Wailea Ekahi Village

Experience the charm of this beautifully renovated condo in Wailea Ekahi Village, completed in December 2020. This spacious top-floor unit offers stunning panoramic ocean views, making it an ideal retreat for travelers seeking tranquility and luxury.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 3
Hawaii> Wailea
from $585 
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Luxury Wailea Beach Villas Penthouse with Ocean Views
Luxury Wailea Beach Villas Penthouse with Ocean Views
Luxury Wailea Beach Villas Penthouse with Ocean Views

Luxury Wailea Beach Villas Penthouse with Ocean Views

Curated with our guests in mind, Wailea Beach Villas PH111 offers a perfect blend of indoor luxury and outdoor tranquility. The outdoor elements are just as immaculate as the interiors, featuring a private lanai with peekaboo ocean views and lush tropical greenery, ideal for relaxing or entertaining.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,325 
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Luxury Maui Condo at Ho'olei 93-3 Near Wailea Beach
Luxury Maui Condo at Ho'olei 93-3 Near Wailea Beach
Luxury Maui Condo at Ho'olei 93-3 Near Wailea Beach

Luxury Maui Condo at Ho'olei 93-3 Near Wailea Beach

Welcome to Ho'olei 93-3 by Gather, a luxurious three-bedroom, three-and-a-half-bathroom condo nestled within the exclusive gated community of Ho'olei in Wailea, Maui. Perfectly positioned just across from Wailea Beach and the Grand Wailea Resort, this residence offers a blend of elegance, comfort, and unparalleled proximity to Maui's top attractions.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Wailea
from $1,303 
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Wailea Grand Champions Villas 2-Bedroom Condo
Wailea Grand Champions Villas 2-Bedroom Condo
Wailea Grand Champions Villas 2-Bedroom Condo

Wailea Grand Champions Villas 2-Bedroom Condo

Located in the heart of Wailea, this charming upstairs condo offers the perfect base for exploring Maui's top attractions. With a prime central location, you can walk to tennis courts, golf courses, shopping at the Shops at Wailea, and a variety of dining options, from casual eateries to fine dining establishments.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $473 
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Wailea Ekahi 54D Ocean View Condo with Luxuries
Wailea Ekahi 54D Ocean View Condo with Luxuries
Wailea Ekahi 54D Ocean View Condo with Luxuries

Wailea Ekahi 54D Ocean View Condo with Luxuries

Experience the beauty of Maui from Wailea Ekahi 54D, a beautifully appointed second-floor condo offering breathtaking ocean and West Maui mountain views. This one-bedroom, two-bath residence features a spacious, airy layout with vaulted ceilings in the living and dining areas, creating an open, inviting atmosphere.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $582 
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Wailea Grand Champions 31 Luxury Maui Condo
Wailea Grand Champions 31 Luxury Maui Condo
Wailea Grand Champions 31 Luxury Maui Condo

Wailea Grand Champions 31 Luxury Maui Condo

Experience the perfect blend of comfort, style, and convenience at Wailea Grand Champions 31, a beautifully updated two-bedroom, two-bathroom condo nestled in the heart of Wailea Maui. This spacious 1,069 sq. ft. residence offers modern upgrades including granite countertops, new cabinetry, and state-of-the-art appliances, ensuring a luxurious stay for all guests.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Wailea
from $480 
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Modern Luxury Family Retreat in Wailea with New Everything
Modern Luxury Family Retreat in Wailea with New Everything
Modern Luxury Family Retreat in Wailea with New Everything

Modern Luxury Family Retreat in Wailea with New Everything

Discover this stunning, fully renovated family-friendly condo in Wailea, featuring brand-new everything. The unit was completely updated in summer 2021, offering a luxurious and comfortable stay for your Hawaiian getaway.
Inside, you'll find a modern, fully equipped kitchen with new appliances and a stylish, high-quality dining setup.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $490 
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Luxury Wailea Grand Champions 43 Vacation Condo
Luxury Wailea Grand Champions 43 Vacation Condo
Luxury Wailea Grand Champions 43 Vacation Condo

Luxury Wailea Grand Champions 43 Vacation Condo

Welcome to Wailea Grand Champions 43, a beautifully appointed vacation condo nestled in the heart of Wailea, Maui. This spacious 1,371 sq. ft. ground-floor residence offers a perfect blend of comfort, style, and convenience, making it an ideal retreat for families, couples, or groups seeking a luxurious island getaway.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $479 
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Wailea Ekahi 38F Ocean View Condo with Pool
Wailea Ekahi 38F Ocean View Condo with Pool
Wailea Ekahi 38F Ocean View Condo with Pool

Wailea Ekahi 38F Ocean View Condo with Pool

Experience the perfect Maui getaway at Wailea Ekahi 38F, a stunning second-floor condo offering panoramic ocean views and luxurious amenities. This spacious two-bedroom, two-bathroom residence seamlessly combines modern comfort with island charm, making it an ideal retreat for families, couples, or friends seeking relaxation and adventure.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $702 
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Luxury Maui Ocean View Villa with Pool & Beach Access
Luxury Maui Ocean View Villa with Pool & Beach Access
Luxury Maui Ocean View Villa with Pool & Beach Access

Luxury Maui Ocean View Villa with Pool & Beach Access

This stunning Maui villa offers a perfect blend of luxury and comfort in a secluded neighborhood setting. The property is hotel zoned and unaffected by recent legislation, ensuring a smooth stay.
Step into a spacious floor plan with breathtaking ocean views that will make every moment special.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Wailea
from $1,600 
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Wailea Grand Champions 71 Ocean & Fairway Views
Wailea Grand Champions 71 Ocean & Fairway Views
Wailea Grand Champions 71 Ocean & Fairway Views

Wailea Grand Champions 71 Ocean & Fairway Views

Welcome to Wailea Grand Champions 71, a beautifully renovated ground-floor condo offering breathtaking fairway and ocean views from the living room and private lanai. This spacious two-bedroom, two-bath residence comfortably accommodates up to six guests, making it perfect for family vacations or group getaways.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $475 
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Makena Surf B106 Beachfront Condo Maui
Makena Surf B106 Beachfront Condo Maui
Makena Surf B106 Beachfront Condo Maui

Makena Surf B106 Beachfront Condo Maui

Welcome to Makena Surf B106, a beautifully appointed two-bedroom beachfront suite offering breathtaking ocean views and easy access to Maui’s pristine beaches. Spanning 1,510 square feet, this ground-floor condo combines luxury and comfort with elegant tray ceilings, exquisite wood cabinetry, and contemporary tropical furnishings that create a warm, inviting atmosphere.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,065 
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Wailea Beach Villas PH410 Oceanview Penthouse
Wailea Beach Villas PH410 Oceanview Penthouse
Wailea Beach Villas PH410 Oceanview Penthouse

Wailea Beach Villas PH410 Oceanview Penthouse

Experience the ultimate Maui getaway at Wailea Beach Villas PH410, a luxurious fourth-floor penthouse offering spectacular views of the Pacific Ocean, Wailea Beach, and neighboring islands. Accessible via your private elevator landing, this spacious 1,900 sq.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,598 
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Wailea Grand Champions Villa 73 - Luxury Maui Stay
Wailea Grand Champions Villa 73 - Luxury Maui Stay
Wailea Grand Champions Villa 73 - Luxury Maui Stay

Wailea Grand Champions Villa 73 - Luxury Maui Stay

Welcome to Wailea Grand Champions Villa 73, a beautifully renovated vacation home nestled in the heart of Wailea, Maui. This spacious ground-floor condo offers a perfect blend of luxury and comfort, ideal for a memorable Maui getaway.
As you step inside, you'll be greeted by a bright, open-concept living space with contemporary finishes and stylish decor.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $430 
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Luxury Polo Beach Condo with Ocean Views in Maui
Luxury Polo Beach Condo with Ocean Views in Maui
Luxury Polo Beach Condo with Ocean Views in Maui

Luxury Polo Beach Condo with Ocean Views in Maui

Welcome to your perfect Maui retreat at Polo Beach Club, a premier oceanfront condominium offering stunning views and luxurious comfort. This beautifully remodeled two-bedroom, two-bath unit spans approximately 1,200 square feet on a single level, blending natural Hawaiian charm with modern upgrades.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Wailea
from $885 
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Secluded Maui Condo at Wailea Ekahi Village
Secluded Maui Condo at Wailea Ekahi Village
Secluded Maui Condo at Wailea Ekahi Village

Secluded Maui Condo at Wailea Ekahi Village

Experience a tranquil and private Maui escape at Wailea Ekahi Village 39A, a beautifully appointed ground-floor condo nestled behind lush tropical foliage. This secluded retreat offers a perfect blend of comfort and natural beauty, ideal for unwinding after exploring Maui's scenic spots.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Wailea
from $492 
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Luxury Maui Condo Near Wailea Beach and Golf
Luxury Maui Condo Near Wailea Beach and Golf
Luxury Maui Condo Near Wailea Beach and Golf

Luxury Maui Condo Near Wailea Beach and Golf

Experience the perfect Maui getaway at Wailea Grand Champions 95, a spacious and beautifully appointed three-bedroom condo nestled among lush tropical landscaping and rolling green fairways. This rental combines comfort and luxury, making it ideal for families or groups seeking a memorable escape in paradise.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $604 
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Wailea Elua Village Beachfront Condo with Pool
Wailea Elua Village Beachfront Condo with Pool
Wailea Elua Village Beachfront Condo with Pool

Wailea Elua Village Beachfront Condo with Pool

Welcome to Wailea Elua Village #2301, a stunning vacation condominium nestled directly on the pristine sugar sand of Ulua Beach. This beautifully updated unit boasts new living room and lanai furniture, creating an inviting and comfortable atmosphere for your Maui holiday.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,000 
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Wailea Elua Village #1001 Oceanfront Condo
Wailea Elua Village #1001 Oceanfront Condo
Wailea Elua Village #1001 Oceanfront Condo

Wailea Elua Village #1001 Oceanfront Condo

Discover the stunning Wailea Elua Village #1001, a recently renovated oceanfront retreat offering breathtaking panoramic views of the Pacific. This ground-floor condo provides an ideal blend of modern comfort and natural beauty, making it perfect for your Maui holiday.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $1,245 
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Wailea Beach Villas D302: Luxury Ocean View Retreat
Wailea Beach Villas D302: Luxury Ocean View Retreat
Wailea Beach Villas D302: Luxury Ocean View Retreat

Wailea Beach Villas D302: Luxury Ocean View Retreat

Welcome to Wailea Beach Villas D302, a beautifully renovated luxury residence offering over 2,900 square feet of indoor and outdoor living space. Situated on the upper floor of the exclusive beachfront villas, this stunning retreat provides unobstructed views of the Pacific Ocean, Wailea Beach, and the surrounding resort area.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Wailea
from $2,380 
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Wailea Elua 1203 Oceanfront Condo with Beach Access
Wailea Elua 1203 Oceanfront Condo with Beach Access
Wailea Elua 1203 Oceanfront Condo with Beach Access

Wailea Elua 1203 Oceanfront Condo with Beach Access

Experience the ultimate Maui getaway at Wailea Elua 1203, a luxurious ground-floor one-bedroom, one-bathroom oceanfront condo situated within the prestigious Wailea Elua Village community. Step outside your door and find direct access to Ulua Beach, renowned for its gentle surf perfect for swimming and snorkeling, making it easy to explore vibrant coral reefs right from your condo.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 2
Hawaii> Wailea
from $739 
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Wailea Grand Champions 97 Luxury Golf Course Condo
Wailea Grand Champions 97 Luxury Golf Course Condo
Wailea Grand Champions 97 Luxury Golf Course Condo

Wailea Grand Champions 97 Luxury Golf Course Condo

Experience the perfect Maui escape at Wailea Grand Champions 97, a beautifully appointed ground-floor condo offering stunning views of the Wailea Blue Golf Course. This 1-bedroom, 2-bathroom residence spans 1,069 square feet and combines elegant design with modern comforts to ensure a memorable vacation.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $427 
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Luxury 3-Bed Maui Ocean View Condo at Ho'olei
Luxury 3-Bed Maui Ocean View Condo at Ho'olei
Luxury 3-Bed Maui Ocean View Condo at Ho'olei

Luxury 3-Bed Maui Ocean View Condo at Ho'olei

5-bath condo perched atop the fourth tier of the exclusive Ho'olei community in Maui. Completely remodeled in 2023, this spacious residence offers breathtaking ocean and island views from multiple lanais, perfect for relaxing and entertaining. The open-concept living area features a large lounge, a fully equipped kitchen with Mr.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Wailea
from $1,524 
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Wailea Beach Villas Penthouse 406 Ocean View
Wailea Beach Villas Penthouse 406 Ocean View
Wailea Beach Villas Penthouse 406 Ocean View

Wailea Beach Villas Penthouse 406 Ocean View

Experience the ultimate Maui escape at Wailea Beach Villas Penthouse 406, a stunning 1,900 sq. ft. oceanfront retreat offering breathtaking Pacific Ocean and island views. This upscale penthouse features two spacious bedrooms and two bathrooms, perfect for relaxation and comfort.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,485 
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Stylish Maui Villa with Golf Course Views
Stylish Maui Villa with Golf Course Views
Stylish Maui Villa with Golf Course Views

Stylish Maui Villa with Golf Course Views

Villa 104 at Wailea Grand Champions Villas offers a perfect blend of style, comfort, and convenience for your Maui getaway. This modern condo features striking golf course views and a thoughtfully curated interior that captures the island’s vibrant spirit.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $435 
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Wailea Grand Champions Villa 111 - Maui Condo
Wailea Grand Champions Villa 111 - Maui Condo
Wailea Grand Champions Villa 111 - Maui Condo

Wailea Grand Champions Villa 111 - Maui Condo

Experience the comfort and relaxed island vibe of Wailea Grand Champions Villa 111, a spacious two-bedroom, two-bath condo ideally situated in the heart of Maui's premier resort area. This vacation rental comfortably accommodates up to six guests, making it perfect for families or groups of friends seeking a memorable Maui escape.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $474 
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Makena Surf Oceanfront Condo with Pool & Beach Access
Makena Surf Oceanfront Condo with Pool & Beach Access
Makena Surf Oceanfront Condo with Pool & Beach Access

Makena Surf Oceanfront Condo with Pool & Beach Access

Makena Surf B205 is a stunning oceanfront vacation home located within the exclusive Makena Surf resort on the beautiful Po'olenalena Beach in Maui. This second-floor condo offers a peaceful retreat, ideal for families or couples seeking privacy and relaxation in a tropical paradise.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $922 
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Stunning Ocean View Condo in Wailea with Modern Upgrades
Stunning Ocean View Condo in Wailea with Modern Upgrades
Stunning Ocean View Condo in Wailea with Modern Upgrades

Stunning Ocean View Condo in Wailea with Modern Upgrades

Immerse yourself in paradise with this beautifully updated top-floor condo at Grand Champs in Wailea. Boasting one of the best ocean views in the complex, this 2-bedroom, 2-bath residence offers a perfect blend of comfort, style, and natural beauty.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $358 
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Wailea Grand Champions 121 Ground-Floor Condo
Wailea Grand Champions 121 Ground-Floor Condo
Wailea Grand Champions 121 Ground-Floor Condo

Wailea Grand Champions 121 Ground-Floor Condo

Experience the comfort and convenience of Wailea Grand Champions 121, a beautifully appointed ground-floor condo perfect for your Maui getaway. Spanning 1,069 sq. , this residence offers garden views and easy access from your parking spot, making unpacking and beach gear transportation hassle-free.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $435 
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Luxury Wailea Elua Village Condo with Ocean Views
Luxury Wailea Elua Village Condo with Ocean Views
Luxury Wailea Elua Village Condo with Ocean Views

Luxury Wailea Elua Village Condo with Ocean Views

Welcome to Wailea Elua Village #1603, a stunning condo boasting some of the best ocean views on Maui. Located within one of the most prestigious and beautifully maintained properties, this residence offers an unparalleled island experience. The condo has been thoughtfully updated with high-quality finishes, handcrafted local art, and elegant decor that create a luxurious and inviting atmosphere.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $1,437 
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Luxury Wailea Beach Villas Penthouse with Ocean Views
Luxury Wailea Beach Villas Penthouse with Ocean Views
Luxury Wailea Beach Villas Penthouse with Ocean Views

Luxury Wailea Beach Villas Penthouse with Ocean Views

Welcome to Penthouse 309 at Wailea Beach Villas, a stunning ocean view residence that combines luxury, cultural charm, and privacy. Spanning 2,520 square feet, this third-floor suite offers exclusive access via a private elevator, ensuring a tranquil retreat.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Wailea
from $1,863 
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Grand Champions #152 Maui Golf Course View
Grand Champions #152 Maui Golf Course View
Grand Champions #152 Maui Golf Course View

Grand Champions #152 Maui Golf Course View

Discover the perfect Maui escape at Grand Champions #152, a beautifully decorated second-floor condo offering breathtaking views of manicured fairways, putting greens, and tee boxes at the Wailea Golf Course. The tropical decor, featuring floral print furniture, framed Hawaiian shirt artwork, and metal reef fish accents, creates a vibrant island ambiance that reminds you you're on Maui.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $426 
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Charming 1-Bedroom Condo in Ekahi Village Maui
Charming 1-Bedroom Condo in Ekahi Village Maui
Charming 1-Bedroom Condo in Ekahi Village Maui

Charming 1-Bedroom Condo in Ekahi Village Maui

Welcome to your ideal Maui retreat located in the heart of Ekahi Village, just a short, flat walk of less than four minutes to the stunning Keawakapu Beach. This private, ground-floor one-bedroom condo offers a peaceful, smoke-free environment with easy access to the beach and all the amenities Ekahi Village has to offer.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> wailea
from $446 
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Luxury Ho'olei Villa with Ocean Views and Pool
Luxury Ho'olei Villa with Ocean Views and Pool
Luxury Ho'olei Villa with Ocean Views and Pool

Luxury Ho'olei Villa with Ocean Views and Pool

Stay longer, enjoy more! Book 10+ nights and receive a free mid-stay clean. Book 14+ nights and get one night free! This luxurious Ho'olei Villa offers stunning ocean views and top-tier amenities. The spacious open floor plan includes a large private lanai that seamlessly connects indoor and outdoor living, perfect for relaxing or entertaining.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,931 
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Charming Tiki Tiki Studio in Wailea’s Paradise
Charming Tiki Tiki Studio in Wailea’s Paradise
Charming Tiki Tiki Studio in Wailea’s Paradise

Charming Tiki Tiki Studio in Wailea’s Paradise

Discover Tiki Tiki, a charming studio nestled in the heart of Wailea, offering a true piece of paradise for your Hawaiian escape. This special retreat is perfect for honeymooners, couples, or anyone seeking a peaceful tropical getaway. The studio exudes a zen ambiance, designed to refresh and rejuvenate guests after a day of exploring the island.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Wailea
from $495 
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