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 Grand Champions Villas Condo with Ocean Views
Wailea Grand Champions Villas Condo with Ocean Views
Wailea Grand Champions Villas Condo with Ocean Views

Wailea Grand Champions Villas Condo with Ocean Views

Welcome to Wailea Grand Champions Villas Condo #188, your perfect Maui retreat. This spacious, meticulously updated top-floor condo offers a tranquil escape with stunning peek-a-boo ocean views and garden vistas. Nestled between the Wailea Blue golf course and Wailea Tennis Club, your stay includes access to premier golf and tennis amenities, with discounted rates and clinics available for guests.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $558 
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Wailea Ekahi Village 20G Renovated Vacation Condo
Wailea Ekahi Village 20G Renovated Vacation Condo
Wailea Ekahi Village 20G Renovated Vacation Condo

Wailea Ekahi Village 20G Renovated Vacation Condo

Upgrades galore as of July 2025. The condominium will be unavailable from May - July 2025 due to renovations. Stay with Wailea Rentals at Wailea Ekahi Village 20G. You and your guests will enjoy premier accommodations, furnishings and holiday experiences at this top-floor Wailea Ekahi vacation home.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $531 
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Luxury Maui Condo at Wailea Grand Champions
Luxury Maui Condo at Wailea Grand Champions
Luxury Maui Condo at Wailea Grand Champions

Luxury Maui Condo at Wailea Grand Champions

Welcome to Wailea Grand Champions 183, a beautifully appointed condo offering the perfect blend of comfort and style in Maui's paradise. This spacious two-bedroom, two-bathroom residence provides an ideal retreat for travelers seeking a memorable Hawaiian escape.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $475 
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Renovated Ocean View Condo in Wailea Maui
Renovated Ocean View Condo in Wailea Maui
Renovated Ocean View Condo in Wailea Maui

Renovated Ocean View Condo in Wailea Maui

Experience the ultimate Maui escape in our fully renovated top-floor condo located in the prestigious Grand Champions Villas in Wailea. This luxurious one-bedroom, two-bath unit comfortably accommodates two adults, offering stunning fairway and partial ocean views from its private lanai.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 2
Hawaii> Wailea
from $283 
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Luxurious 1-Bedroom Condo Near Keawakapu Beach
Luxurious 1-Bedroom Condo Near Keawakapu Beach
Luxurious 1-Bedroom Condo Near Keawakapu Beach

Luxurious 1-Bedroom Condo Near Keawakapu Beach

Discover this beautifully remodeled 1-bedroom, 2-bath condo at The Palms at Wailea, offering 1022 sq. ft. of modern elegance and comfort. Located on the ground floor for easy access, the unit features a spacious lanai with two chaise lounges, perfect for relaxing and enjoying the Maui sunshine.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $340 
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Luxurious Oceanview Condo in Maui's Wailea Elua
Luxurious Oceanview Condo in Maui's Wailea Elua
Luxurious Oceanview Condo in Maui's Wailea Elua

Luxurious Oceanview Condo in Maui's Wailea Elua

Welcome to your perfect Maui getaway! This stunning condo in Wailea Elua Village offers a seamless blend of luxury and comfort with a thoughtfully renovated interior. Inside, you'll find new Ohia wood cabinets, stylish sandstone tile flooring, and top-of-the-line Miele appliances, creating a modern and inviting kitchen space.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,512 
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Wailea Elua Ocean-View Condo with Beach Access
Wailea Elua Ocean-View Condo with Beach Access
Wailea Elua Ocean-View Condo with Beach Access

Wailea Elua Ocean-View Condo with Beach Access

Experience the ultimate Maui escape in this spacious 1259 sqft Wailea Elua condo nestled on 24 scenic acres. Just steps from Ulua Beach, renowned for swimming, snorkeling, and unforgettable sunsets, this property offers the perfect blend of comfort and luxury.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,094 
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Wailea Palms 1904: Stylish 2-Bed Maui Condo
Wailea Palms 1904: Stylish 2-Bed Maui Condo
Wailea Palms 1904: Stylish 2-Bed Maui Condo

Wailea Palms 1904: Stylish 2-Bed Maui Condo

Welcome to Palms at Wailea 1904, a beautifully updated and conveniently located 2-bedroom, 2-bathroom condo in the scenic Wailea area of Maui. This inviting retreat is ideal for families or couples seeking both comfort and luxury during their Hawaiian getaway.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $474 
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Elua Village Beachfront Maui Condo with Pool
Elua Village Beachfront Maui Condo with Pool
Elua Village Beachfront Maui Condo with Pool

Elua Village Beachfront Maui Condo with Pool

Welcome to your dream Maui vacation at Elua Village, a private beachfront resort nestled in the heart of Wailea on the stunning Ulua Beach. Spanning 24 acres of lush lawns and gardens, this resort offers a perfect blend of tranquility and adventure.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $1,069 
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Wailea Ekolu 706 Ocean View Condo with Pool
Wailea Ekolu 706 Ocean View Condo with Pool
Wailea Ekolu 706 Ocean View Condo with Pool

Wailea Ekolu 706 Ocean View Condo with Pool

Experience the beauty of Maui at Wailea Ekolu 706, a spacious and beautifully decorated condo perched on the second floor with sweeping ocean views. Towering oleander and bougainvillea adorn the lush front entry, welcoming you into a tropical paradise.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $498 
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Wailea Ekahi Beachfront Condo with Pool
Wailea Ekahi Beachfront Condo with Pool
Wailea Ekahi Beachfront Condo with Pool

Wailea Ekahi Beachfront Condo with Pool

Welcome to your perfect Maui getaway in this beautifully remodeled, fully furnished ground-floor condo located in Wailea Ekahi. Situated directly on the beach, this private corner unit offers unmatched convenience and tranquility.
Our home, unit 40A, is in pristine condition with tasteful island decor, fresh appliances, and high-end fixtures, providing a comfortable and stylish retreat.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $337 
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Wailea Ekolu 1107 Ocean View Ground-Floor Condo
Wailea Ekolu 1107 Ocean View Ground-Floor Condo
Wailea Ekolu 1107 Ocean View Ground-Floor Condo

Wailea Ekolu 1107 Ocean View Ground-Floor Condo

Immerse yourself in the beauty of Maui at Wailea Ekolu 1107, a charming ground-floor condo offering breathtaking ocean, mountain, and Lana'i vistas. This 2-bedroom, 2-bath residence spans 1,316 sq. ft. and is thoughtfully decorated to create a relaxing tropical retreat.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $439 
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Wailea Elua 1703 Oceanfront Vacation Condo
Wailea Elua 1703 Oceanfront Vacation Condo
Wailea Elua 1703 Oceanfront Vacation Condo

Wailea Elua 1703 Oceanfront Vacation Condo

Elua 1703 offers a unique oceanfront retreat in Wailea, Maui, perfectly positioned directly in front of Ulua Beach and the Wailea Beachfront Walking Path. Surrounded on three sides by lush, meticulously landscaped gardens and lawns, this ground-floor condo provides unmatched privacy and panoramic ocean views without neighboring obstructing structures.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,395 
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Wailea Ekolu 1607 Luxury Maui Condo with Golf Views
Wailea Ekolu 1607 Luxury Maui Condo with Golf Views
Wailea Ekolu 1607 Luxury Maui Condo with Golf Views

Wailea Ekolu 1607 Luxury Maui Condo with Golf Views

Discover Wailea Ekolu 1607, a beautifully appointed one-bedroom, two-bathroom condo nestled in the scenic Wailea community. This ground-floor residence boasts 1,069 sq ft of living space with serene views of the lush Wailea Blue Golf Course, providing an ideal setting for your Hawaiian holiday.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $437 
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Luxury Beachfront Condo at Wailea Elua Village
Luxury Beachfront Condo at Wailea Elua Village
Luxury Beachfront Condo at Wailea Elua Village

Luxury Beachfront Condo at Wailea Elua Village

Experience the ultimate Maui retreat in this meticulously renovated single-level luxury condo at Wailea Elua Village. From the moment you step inside, you're greeted with sweeping ocean vistas visible through fleetwood sliding doors that frame the stunning scenery.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,083 
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Wailea Elua 905 Beachfront Luxury Condo Maui
Wailea Elua 905 Beachfront Luxury Condo Maui
Wailea Elua 905 Beachfront Luxury Condo Maui

Wailea Elua 905 Beachfront Luxury Condo Maui

Escape to Wailea Elua 905, a beautifully appointed 3-bedroom, 2-bathroom condo nestled along Maui's scenic coastline. This spacious residence offers a perfect blend of comfort and elegance, ideal for families or friends seeking a luxurious beachside retreat.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $901 
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Luxury 3BR Condo at Wailea Grand Champion Villas
Luxury 3BR Condo at Wailea Grand Champion Villas
Luxury 3BR Condo at Wailea Grand Champion Villas

Luxury 3BR Condo at Wailea Grand Champion Villas

Bldg. 16 - Unit #153 - A ground-floor, front-row condo in the Wailea Grand Champion Villas, offering a luxurious 3-bedroom + 2-bath retreat. Recently upgraded throughout, the unit features split A/C systems, a modern kitchen, and stunning sunset views overlooking the Wailea Ol' Blue Golf Course and the West Maui mountains.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $686 
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Makena Surf F109 Oceanfront Maui Condo
Makena Surf F109 Oceanfront Maui Condo
Makena Surf F109 Oceanfront Maui Condo

Makena Surf F109 Oceanfront Maui Condo

Makena Surf F109 is a beautiful oceanfront condo located on the stunning shores of Maui. Situated just steps from the beach, this ground-floor unit offers unobstructed ocean views from a private lanai, perfect for enjoying Maui’s natural beauty.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $826 
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Luxury Family-Friendly Wailea Condo with Ocean Views
Luxury Family-Friendly Wailea Condo with Ocean Views
Luxury Family-Friendly Wailea Condo with Ocean Views

Luxury Family-Friendly Wailea Condo with Ocean Views

Experience a luxurious, family-friendly retreat in the heart of Wailea at The Palms. This completely renovated condo features brand new everything—modern appliances, stylish decor, and high-end linens. The spacious unit boasts a fully equipped, deluxe kitchen with all new appliances, perfect for preparing memorable meals.

  • 2 bedroom
  • 1 bathroom
  • Sleeps 6
Hawaii> Wailea
from $517 
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Luxury Oceanfront Condo at Polo Beach Club Wailea
Luxury Oceanfront Condo at Polo Beach Club Wailea
Luxury Oceanfront Condo at Polo Beach Club Wailea

Luxury Oceanfront Condo at Polo Beach Club Wailea

Experience the ultimate beachfront getaway at Polo Beach Club 409, a luxurious oceanfront condo nestled in the heart of Wailea Maui. This stunning two-bedroom, two-bathroom residence offers direct access to the pristine Polo Beach and panoramic ocean views from nearly every room, including the living area, kitchen, and primary bedroom.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $780 
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Luxury Wailea Villa with Pool and Ocean Views
Luxury Wailea Villa with Pool and Ocean Views
Luxury Wailea Villa with Pool and Ocean Views

Luxury Wailea Villa with Pool and Ocean Views

Experience the stunning beauty of Wailea from this spacious and stylish villa located in the secluded Grand Champions resort. Set in a peaceful position, the villa offers a perfect retreat with breathtaking views from the lanai. Relax on the outdoor space, unwind with a good book, or catch your favorite shows on streaming services.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 2
Hawaii> Wailea
from $571 
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Wailea Elua 2204 Ocean View Luxury Villa
Wailea Elua 2204 Ocean View Luxury Villa
Wailea Elua 2204 Ocean View Luxury Villa

Wailea Elua 2204 Ocean View Luxury Villa

Experience breathtaking panoramic views of the Pacific Ocean from Wailea Elua 2204, a beautifully renovated second-floor villa in South Maui. This luxurious residence features expansive living spaces with fully stacking sliding doors that open to a private lanai, allowing guests to immerse themselves in the warm sea breeze and listen to the soothing sound of waves.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,184 
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Makena Surf F304 Oceanfront Maui Condo
Makena Surf F304 Oceanfront Maui Condo
Makena Surf F304 Oceanfront Maui Condo

Makena Surf F304 Oceanfront Maui Condo

Experience the ultimate Maui getaway at Makena Surf F304, a stunning oceanfront condo nestled in the beautiful Makena region. This third-floor residence offers breathtaking views of the Pacific Ocean, perfect for couples or families seeking relaxation and luxury.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $930 
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Luxurious Wailea Beach Villas Penthouse with Bali Style
Luxurious Wailea Beach Villas Penthouse with Bali Style
Luxurious Wailea Beach Villas Penthouse with Bali Style

Luxurious Wailea Beach Villas Penthouse with Bali Style

Experience the sophisticated charm of Wailea Beach Villas Penthouse 104, a beautifully designed residence blending Bali influence with rustic touches to create a memorable escape. This 2,000 sq. ft. garden-view penthouse is located within a secure, gated community just steps from Wailea Beach and the renowned Shops at Wailea, offering unparalleled convenience and luxury.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,287 
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Wailea Ekahi Oceanfront 1BR Condo with Sunset Views
Wailea Ekahi Oceanfront 1BR Condo with Sunset Views
Wailea Ekahi Oceanfront 1BR Condo with Sunset Views

Wailea Ekahi Oceanfront 1BR Condo with Sunset Views

Experience the beauty of Wailea in this beautifully remodeled 1-bedroom, 2-bath condo located on the front row of Wailea Ekahi. This second-floor unit offers spectacular ocean views from every room, thanks to vaulted ceilings and extra-large sliding glass doors that create a bright, airy ambiance.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $457 
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Wailea Grand Champion Villas Beachfront Condo
Wailea Grand Champion Villas Beachfront Condo
Wailea Grand Champion Villas Beachfront Condo

Wailea Grand Champion Villas Beachfront Condo

Escape to this stunning front-row 2-bedroom, 2-bathroom condominium at Wailea Grand Champion Villas, offering an upscale Maui retreat. Recently upgraded with split A/C systems, a modern kitchen, and breathtaking sunset views over the Wailea Ol' Blue Golf Course towards the West Maui mountains, this property promises both comfort and elegance.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $488 
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Ekahi Oceanview Condo in Maui with Pools
Ekahi Oceanview Condo in Maui with Pools
Ekahi Oceanview Condo in Maui with Pools

Ekahi Oceanview Condo in Maui with Pools

Discover this beautifully maintained condo in Ekahi Village, Maui, featuring one large bedroom plus a sofa bed in the living room, two full baths, and stunning ocean views from the lanai and kitchen window. Located in a tranquil greenbelt area, the second-floor unit is surrounded by lush tropical gardens and offers a peaceful retreat with modern amenities.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $453 
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Luxurious Maui Condo with Ocean Views at Wailea
Luxurious Maui Condo with Ocean Views at Wailea
Luxurious Maui Condo with Ocean Views at Wailea

Luxurious Maui Condo with Ocean Views at Wailea

Aloha! Discover the warmth and beauty of Maui at our stunning condo in Wailea Ekolu Village. Located on the ground floor of highly sought-after building #3, this spacious one-bedroom, two-bath condominium offers an ideal retreat with breathtaking ocean views and modern comforts.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $405 
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Luxury Maui Villa with Ocean Views and Modern Comforts
Luxury Maui Villa with Ocean Views and Modern Comforts
Luxury Maui Villa with Ocean Views and Modern Comforts

Luxury Maui Villa with Ocean Views and Modern Comforts

Call this private piece of paradise your home-away-from-home, offering stunning panoramic views of Maui and the Pacific Ocean, complemented by luxurious interior touches. Spanning 2,500 square feet, this contemporary residence captures the essence of Hawaiian elegance and comfort, blending indoor and outdoor living seamlessly.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,479 
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Wailea Ekahi Village 23C Renovated Garden Condo
Wailea Ekahi Village 23C Renovated Garden Condo
Wailea Ekahi Village 23C Renovated Garden Condo

Wailea Ekahi Village 23C Renovated Garden Condo

Welcome to Wailea Ekahi Village 23C, a beautifully renovated ground-floor condo offering a serene island escape. Nestled within 34 acres of lush tropical gardens, this residence combines modern comfort with Maui's natural beauty. Fully updated in fall 2024, the condo features stylish furnishings and decor that foster a relaxed, island-inspired ambiance.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $516 
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Wailea Beach Villas PH207 Luxury Oceanview Penthouse
Wailea Beach Villas PH207 Luxury Oceanview Penthouse
Wailea Beach Villas PH207 Luxury Oceanview Penthouse

Wailea Beach Villas PH207 Luxury Oceanview Penthouse

Step into Wailea Beach Villas PH207 and be greeted by an open, airy layout that combines comfort and elegance. The spacious living room flows seamlessly into a quiet den with traditional shoji screen doors, perfect for relaxing or working in peace.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,292 
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Spacious 3BR Condo with Ocean Views in Wailea
Spacious 3BR Condo with Ocean Views in Wailea
Spacious 3BR Condo with Ocean Views in Wailea

Spacious 3BR Condo with Ocean Views in Wailea

Discover this stunning 3-bedroom, 2-bathroom condo at Grand Champions Villas in Wailea. Recently renovated, it offers ocean and garden views in a peaceful location backing onto a golf course. The spacious living area features a fully equipped kitchen with stainless steel appliances, granite counters, and all essentials including BBQ tools and beach gear like Tommy Bahama beach chairs, boogie boards, umbrellas, and coolers.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Wailea
from $635 
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Stunning Wailea Ocean View Condo with Private Lanais
Stunning Wailea Ocean View Condo with Private Lanais
Stunning Wailea Ocean View Condo with Private Lanais

Stunning Wailea Ocean View Condo with Private Lanais

Experience breathtaking panoramic ocean vistas from this exquisite Wailea condo situated in a private, peaceful setting. This top-tier unit offers unobstructed views from the living room, dining area, kitchen, master bedroom, and two lanais, making it an ideal haven for relaxation and enjoyment.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Wailea
from $508 
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Luxury Maui Penthouse with Ocean Views at Wailea Beach Villas
Luxury Maui Penthouse with Ocean Views at Wailea Beach Villas
Luxury Maui Penthouse with Ocean Views at Wailea Beach Villas

Luxury Maui Penthouse with Ocean Views at Wailea Beach Villas

5-bedroom, 2-bath villa offering over 2,200 sq ft of elegant living space and a 280 sq ft lanai with breathtaking ocean and pool views. Nestled amidst lush tropical landscaping on 11 acres, this condo combines privacy with proximity to Wailea's finest attractions.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,298 
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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

Escape to the serene beauty of Maui at Wailea Beach Villas Penthouse 411, a luxurious 1,900 sq. ft. oceanview residence on the fourth floor. This stunning two-bedroom, two-bathroom penthouse offers the perfect blend of comfort, privacy, and breathtaking views, making it an ideal retreat for families or groups of friends.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,577 
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Luxury 3-Bedroom Condo in Wailea with Modern Amenities
Luxury 3-Bedroom Condo in Wailea with Modern Amenities
Luxury 3-Bedroom Condo in Wailea with Modern Amenities

Luxury 3-Bedroom Condo in Wailea with Modern Amenities

Experience a luxurious stay in this stunning, fully remodeled 3-bedroom, 2-bathroom condo located in the desirable Grand Champions Villas in Wailea. The unit boasts all-new furnishings and modern upgrades, ensuring a comfortable and stylish retreat for your Maui vacation.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Wailea
from $655 
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Luxury Beachfront Condo in Wailea Maui
Luxury Beachfront Condo in Wailea Maui
Luxury Beachfront Condo in Wailea Maui

Luxury Beachfront Condo in Wailea Maui

Step into this stunning newly renovated 1536 sq ft beachfront condo in Wailea, Maui, offering breathtaking ocean and Haleakala mountain views. The airy, modern interior features high-end mahogany furnishings and a fully equipped kitchen for your culinary needs.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,044 
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Wailea Beach Villas Penthouse with Ocean Views
Wailea Beach Villas Penthouse with Ocean Views
Wailea Beach Villas Penthouse with Ocean Views

Wailea Beach Villas Penthouse with Ocean Views

Experience unparalleled luxury at Wailea Beach Villas Penthouse 502, a stunning top-floor residence boasting sweeping ocean views and elegant decor. The private elevator landing opens to a spacious living area with floor-to-ceiling windows and sliding glass doors that frame the vibrant blue Pacific Ocean, creating a seamless indoor-outdoor living experience.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $1,593 
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Elegant Maui Ocean View Condo at Ekolu Village
Elegant Maui Ocean View Condo at Ekolu Village
Elegant Maui Ocean View Condo at Ekolu Village

Elegant Maui Ocean View Condo at Ekolu Village

Escape to this stunning 2-bedroom, 2-bath condo nestled on 18 acres of lush tropical foliage bordering the acclaimed Wailea Blue Golf Course. Ekolu Village offers a peaceful retreat free from traffic noise, located less than five minutes from Maui’s beautiful beaches.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $542 
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Ho'olei 21-6 Luxury Maui Villa with Ocean Views
Ho'olei 21-6 Luxury Maui Villa with Ocean Views
Ho'olei 21-6 Luxury Maui Villa with Ocean Views

Ho'olei 21-6 Luxury Maui Villa with Ocean Views

Welcome to Ho'olei 21-6, a brand-new luxury vacation rental managed by Waiola Realty, offering a perfect blend of comfort, style, and stunning ocean vistas in Wailea, Maui. Although new, this villa has a proven track record through our other Ho'olei listings with hundreds of 5-star reviews, ensuring a memorable stay for your family or friends.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Wailea
from $1,406 
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Luxury Wailea Beach Villas Modern Maui I404
Luxury Wailea Beach Villas Modern Maui I404
Luxury Wailea Beach Villas Modern Maui I404

Luxury Wailea Beach Villas Modern Maui I404

Experience the ultimate Maui getaway in this stunning Modern Maui I404 penthouse at Wailea Beach Villas. Managed by Private Paradise Villas, this 2,300 sq ft luxury residence offers breathtaking west-facing views of the Pacific Ocean, Wailea Beach, and mesmerizing sunsets.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,748 
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Luxury Maui Meadows Guesthouse with Pool & Hot Tub
Luxury Maui Meadows Guesthouse with Pool & Hot Tub
Luxury Maui Meadows Guesthouse with Pool & Hot Tub

Luxury Maui Meadows Guesthouse with Pool & Hot Tub

The Maui Meadows Guesthouse offers an exceptional vacation experience just 3/4 mile from eight premier beaches. This spacious 4-bedroom, 5-bath single-story home spans 2,700 sq ft and combines comfort with luxury. Inside, you'll find air conditioning, a 65" streaming TV with NFL RedZone, and a 60" projector and screen in one bedroom, perfect for relaxing after a day on the beach.

  • 4 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Wailea
from $1,464 
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Luxury Ocean View Penthouse Villa at Wailea
Luxury Ocean View Penthouse Villa at Wailea
Luxury Ocean View Penthouse Villa at Wailea

Luxury Ocean View Penthouse Villa at Wailea

Experience the ultimate Hawaiian getaway in this stunning 4th-floor penthouse located within the centrally situated "Penthouse" building of Wailea Beach Villas. 5-bedroom residence offers a perfect blend of luxury, comfort, and style.
The spacious living area is flooded with natural light through floor-to-ceiling windows, creating a cheerful and inviting atmosphere.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,727 
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Luxury Maui Condo Near Ulua Beach with Ocean Views
Luxury Maui Condo Near Ulua Beach with Ocean Views
Luxury Maui Condo Near Ulua Beach with Ocean Views

Luxury Maui Condo Near Ulua Beach with Ocean Views

Discover this beautifully remodeled Maui condo just a minute's walk from the stunning Ulua Beach, renowned for its clear waters and vibrant marine life. From your private lanai, enjoy unobstructed ocean views and soothing sounds of the sea amidst tropical gardens, creating a perfect retreat for relaxation.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Wailea
from $704 
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Remodeled 2BR Condo with Ocean View in Wailea
Remodeled 2BR Condo with Ocean View in Wailea
Remodeled 2BR Condo with Ocean View in Wailea

Remodeled 2BR Condo with Ocean View in Wailea

Welcome to Palms at Wailea 503, your beautifully remodeled sanctuary in paradise! This spacious two-bedroom, two-bath condo is situated in the prestigious Wailea Resort area, offering stunning ocean views and modern comforts. Recently renovated in December 2023, the condo features a fully equipped kitchen with granite countertops, modern appliances, and ample cookware—perfect for preparing delicious meals during your stay.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $545 
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Luxury Wailea Townhome with Ocean Views & Private Elevator
Luxury Wailea Townhome with Ocean Views & Private Elevator
Luxury Wailea Townhome with Ocean Views & Private Elevator

Luxury Wailea Townhome with Ocean Views & Private Elevator

Experience the ultimate island getaway in this luxurious two-story Wailea townhome, offering stunning ocean and pool views. Designed for comfort and convenience, this property sleeps up to 10 guests and features a private elevator, an attached garage, and stylish indoor and outdoor spaces.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Wailea
from $1,312 
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Luxury Oceanview Wailea Beach Villas Penthouse
Luxury Oceanview Wailea Beach Villas Penthouse
Luxury Oceanview Wailea Beach Villas Penthouse

Luxury Oceanview Wailea Beach Villas Penthouse

Experience the ultimate Maui retreat in this luxurious oceanview 3-bedroom, 3-bath penthouse at Wailea Beach Villas. Adorned with monkeypod cabinetry and high-end finishes, this spacious unit offers a perfect blend of modern elegance and Hawaiian charm.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Wailea
from $2,311 
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Elegant 1-Bedroom Maui Condo Near Beach
Elegant 1-Bedroom Maui Condo Near Beach
Elegant 1-Bedroom Maui Condo Near Beach

Elegant 1-Bedroom Maui Condo Near Beach

Discover our beautifully renovated 1-bedroom, 2-bath condo nestled in Wailea Ekahi Village, just moments from pristine beaches and vibrant attractions. This top-floor gem, updated in 2021, combines modern elegance with a relaxed coastal vibe. The open-concept living space is filled with natural light, offering breathtaking views of palm trees and stunning sunsets from the spacious lanai—perfect for sipping drinks or enjoying romantic dinners while soaking in the tropical ambiance.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $513 
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Charming Kihei Condo with 2 King Beds & Amenities
Charming Kihei Condo with 2 King Beds & Amenities
Charming Kihei Condo with 2 King Beds & Amenities

Charming Kihei Condo with 2 King Beds & Amenities

Located in the heart of Kihei, this inviting condo offers a perfect family retreat. The two bedrooms each feature plush king beds with ceiling fans, ensuring restful nights. The bathrooms are equipped with luxurious rainfall showers, providing a spa-like experience.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Wailea
from $452 
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Makena Surf Turquoise Cove Villa with Ocean Views
Makena Surf Turquoise Cove Villa with Ocean Views
Makena Surf Turquoise Cove Villa with Ocean Views

Makena Surf Turquoise Cove Villa with Ocean Views

Welcome to the newly renovated, top-floor ''Turquoise Cove'' Villa - Makena Surf F301. This exceptional property offers unparalleled ocean views and a unique double wrap-around lanai, perfect for enjoying tropical sunsets or catching the sight of whales in season.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Wailea
from $1,832 
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