Makena Surf B201 | 2nd Floor Oceanfront, On the Beach & Turtle ReefFrom $1,403/night · Sleeps 6
South Maui Luxury Villas and Condos
Wailea Vacation Rentals
Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui
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 stay, 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
- Hoolei 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 right for long stays
- Consistently sunny weather and calm swimming beaches
Plan Your Stay in Wailea
Wailea offers the best of South Maui-quiet surroundings, world-class amenities, and stunning natural beauty. Whether you're visiting for a romantic stay or a long-term tropical escape, Wailea vacation rentals provide the right home base for a luxurious island experience.
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Wailea Vacation Rentals Listings
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Wailea Vacation Rentals Map
Makena Surf B201 | 2nd Floor Oceanfront, On the Beach & Turtle ReefFrom $1,403/night · Sleeps 6
Recently Renovated - Stunning Design & ViewsFrom $1,438/night · Sleeps 5
Modern Ocean View Elegance - Wailea Beach Villas PH404From $1,488/night · Sleeps 6
NEW! KBM Resorts | FREE CAR | Wailea Beach Villa | Spacious 3-Bedroom Condo with Sweeping Ocean view! WBV-PH505From $1,627/night · Sleeps 6
Award-Winning Resort & Amenities | Wailea Beach Villas PH104From $1,855/night · Sleeps 6
Recently Renovated - Wailea Golf ViewsFrom $238/night · Sleeps 5
Palms at Wailea Villa 1210 Garden Deluxe 1 BD 2 BAFrom $393/night · Sleeps 2
Ocean View Bliss on Wailea Beach PathFrom $719/night · Sleeps 4
Makena Surf A204 | 3-Sided Ocean & Mountain Views, Beach Access & Turtle ReefFrom $1,033/night · Sleeps 6
Newly Renovated - Professionally Managed | Wailea Elua 706From $1,120/night · Sleeps 4
Ground Floor with Instant Beach Access - Polo Beach 102From $1,268/night · Sleeps 6
Makena Surf B204 | Beachfront, Ocean & Mountain Views, Heated Pool, Hot TubFrom $1,292/night · Sleeps 6
Stunning Wailea Villa with Resort AmenitiesFrom $1,492/night · Sleeps 8
Grand Champions | Ocean View 6 BR, Sleeps 16 | Car Incl. w/ 6+ Nights | GCH ML-3782 by KBMFrom $2,056/night · Sleeps 16
Wailea Ekahi Village 54B – 4 Resort Pools & Pickleball on Keawakapu BeachFrom $217/night · Sleeps 4
Indoor-Outdoor Tropical Living - Wailea Ekahi 47BFrom $220/night · Sleeps 4
Wailea Ekahi Village 49C | Romantic Ocean View Retreat for Two, Beach AccessFrom $280/night · Sleeps 2
Walk to Favorite Beach - Wailea Ekahi 50CFrom $312/night · Sleeps 4
Palms at Wailea Garden Deluxe Villas 1 BD 2 BAFrom $318/night · Sleeps 4
Ekahi 47E | Hot tub | Pool | Sunset ViewsFrom $323/night · Sleeps 4
Palms at Wailea Ocean View Villas 1 Bedroom 2 BathFrom $335/night · Sleeps 4
Wailea Grand Champions 177 | Golf Course Views, Tennis & Walk to Wailea ShopsFrom $340/night · Sleeps 4
Walk to Waves & Snorkeling - Great for FamiliesFrom $340/night · Sleeps 6
Palms at Wailea Garden Villas 1 Bedroom 2 BathFrom $341/night · Sleeps 4
Grand Champions | Ocean View 2 BR, Sleeps 8 | Car Incl. w/ 6+ Nights | GCH ML-1493 by KBMFrom $344/night · Sleeps 8
Wailea Ekolu Village 1203 | Golf Walk-Out, Renovated, Pools & WalkableFrom $348/night · Sleeps 4
Palms at Wailea Villa 1103 Ocean View 1 BD 2 BAFrom $356/night · Sleeps 4
Tropical Garden & Pool Views - Professionally ManagedFrom $374/night · Sleeps 4
Palms at Wailea Villa 2203 Garden Deluxe 1 BD 2 BAFrom $378/night · Sleeps 4
Elevated Ocean Views | Walk to the BeachFrom $395/night · Sleeps 4
Remodeled Ocean View | Wailea Ekolu 703From $396/night · Sleeps 6
Sunset & Ocean Views | Fun Resort AmenitiesFrom $400/night · Sleeps 4
Beachfront 2BR condo in Wailea w/ pool and hot tubFrom $432/night · Sleeps 4
From $1,403/night
Makena Surf B201 | 2nd Floor Oceanfront, On the Beach & Turtle Reef
Wailea, Hawaii
★★★★★ 2 reviews
CORALTREE RESIDENCE COLLECTION presents... Makena Surf B201! Experience an intimate Hawaiian retreat at this carefully updated 2-bedroom second-floor...
From $1,438/night
Recently Renovated - Stunning Design & Views
Wailea, Hawaii
★★★★★ 2 reviews
Welcome to Wailea Elua Village #2108. This two-bedroom, two-bath residence is fully remodeled and redecorated, features an extra-large floor plan of...
From $1,488/night
Modern Ocean View Elegance - Wailea Beach Villas PH404
Wailea, Hawaii
★★★★★ 2 reviews
Wailea Beach Villas Penthouse 404 is a stunning two-bedroom plus den, two-bathroom ocean view residence offering over 1,978 sq. ft. of elegant...
From $1,627/night
NEW! KBM Resorts | FREE CAR | Wailea Beach Villa | Spacious 3-Bedroom Condo with Sweeping Ocean view! WBV-PH505
Wailea, Hawaii
★★★★★ 2 reviews
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more...
From $1,855/night
Award-Winning Resort & Amenities | Wailea Beach Villas PH104
Wailea, Hawaii
★★★★★ 2 reviews
Marvel at the sophisticated style and décor of Wailea Beach Villas Penthouse 104, where a touch of Bali influence seamlessly merges with rustic...
From $238/night
Recently Renovated - Wailea Golf Views
Wailea, Hawaii
★★★★★ 1 reviews
Welcome to Wailea Grand Champions 102, a luxurious 2-bedroom, 2-bathroom residence nestled between the fairways of one of Maui\'s most popular...
From $393/night
Palms at Wailea Villa 1210 Garden Deluxe 1 BD 2 BA
Wailea, Hawaii
★★★★★ 1 reviews
This charming one-bedroom garden-view villa is located in Maui’s sought-after Wailea resort community. With a full kitchen, open concept living area,...
From $719/night
Ocean View Bliss on Wailea Beach Path
Wailea, Hawaii
★★★★★ 1 reviews
Wailea Point is the ultimate in privacy and elegance for those seeking stays of 30 nights or longer. For shorter stays, please select from one of our...
From $1,033/night
Makena Surf A204 | 3-Sided Ocean & Mountain Views, Beach Access & Turtle Reef
Wailea, Hawaii
★★★★★ 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Makena Surf A204! Experience an intimate Hawaiian retreat at this 2-bedroom second-floor condo on...
From $1,120/night
Newly Renovated - Professionally Managed | Wailea Elua 706
Wailea, Hawaii
★★★★★ 1 reviews
Welcome to your dream vacation retreat in Wailea! As you step inside the newly renovated Wailea Elua 706, you\'ll immediately be captivated by the...
From $1,268/night
Ground Floor with Instant Beach Access - Polo Beach 102
Wailea, Hawaii
★★★★★ 1 reviews
Welcome to the serene Polo Beach Club 102, your perfect ocean retreat in Wailea. This stunning 2-bedroom, 2-bathroom condo offers a luxurious escape...
From $1,292/night
Makena Surf B204 | Beachfront, Ocean & Mountain Views, Heated Pool, Hot Tub
Wailea, Hawaii
★★★★★ 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Makena Surf B204Experience an intimate Hawaiian retreat at this peaceful 2-bedroom condo right on...
From $1,492/night
Stunning Wailea Villa with Resort Amenities
Wailea, Hawaii
★★★★★ 1 reviews
Welcome to Wailea Beach Villas Penthouse 205, an elegant retreat that showcases sophisticated furnishings, vibrant colors, and striking artwork. This...
From $2,056/night
Grand Champions | Ocean View 6 BR, Sleeps 16 | Car Incl. w/ 6+ Nights | GCH ML-3782 by KBM
Wailea, Hawaii
★★★★★ 1 reviews
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more...
From $217/night
Wailea Ekahi Village 54B – 4 Resort Pools & Pickleball on Keawakapu Beach
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 54BA recently remodeled 1,180 sq.ft. ground-floor condo with 2 full bathrooms,...
From $220/night
Indoor-Outdoor Tropical Living - Wailea Ekahi 47B
Wailea, Hawaii
Welcome to your tropical retreat at Wailea Ekahi Village 47B—an ideal vacation escape for families or a group of friends. This beautifully...
From $280/night
Wailea Ekahi Village 49C | Romantic Ocean View Retreat for Two, Beach Access
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 49C At 49C, the private lanai walks straight out to the tropical gardens — step...
From $312/night
Walk to Favorite Beach - Wailea Ekahi 50C
Wailea, Hawaii
Experience the ultimate in island luxury with a stay at Wailea Ekahi 50C, a beautiful one-bedroom, one-bathroom vacation rental situated in the heart...
From $318/night
Palms at Wailea Garden Deluxe Villas 1 BD 2 BA
Wailea, Hawaii
Experience elevated island comfort in a deluxe one-bedroom villa with lush garden views, located in Maui’s exclusive Wailea resort community. Enjoy a...
From $323/night
Ekahi 47E | Hot tub | Pool | Sunset Views
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 47E Picture your morning: coffee on a sweeping 224-square-foot lanai, tropical...
From $335/night
Palms at Wailea Ocean View Villas 1 Bedroom 2 Bath
Wailea, Hawaii
Enjoy stunning ocean views from villas featuring a full kitchen, spacious living area, and a private patio; it’s the perfect spot to relax while...
From $340/night
Wailea Grand Champions 177 | Golf Course Views, Tennis & Walk to Wailea Shops
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 177Wailea Grand Champions is an 11-acre country club-style resort set along the...
From $340/night
Walk to Waves & Snorkeling - Great for Families
Wailea, Hawaii
Wailea Ekahi Village tropical vacation condos are situated above Maui's beautiful Keawakapu Beach and close to all the top Wailea resort hotels....
From $341/night
Palms at Wailea Garden Villas 1 Bedroom 2 Bath
Wailea, Hawaii
A peaceful one-bedroom villa with lush garden views, located in Maui’s renowned Wailea Resort community. Perfect for a relaxing getaway, it features...
From $344/night
Grand Champions | Ocean View 2 BR, Sleeps 8 | Car Incl. w/ 6+ Nights | GCH ML-1493 by KBM
Wailea, Hawaii
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more...
From $348/night
Wailea Ekolu Village 1203 | Golf Walk-Out, Renovated, Pools & Walkable
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1203 Step off the private lanai at 1203 and you're on the Wailea Blue Golf Course —...
From $356/night
Palms at Wailea Villa 1103 Ocean View 1 BD 2 BA
Wailea, Hawaii
This ocean-view one-bedroom villa offers a serene retreat with sweeping views of the Pacific. Located within Wailea’s resort community, it includes a...
From $374/night
Tropical Garden & Pool Views - Professionally Managed
Wailea, Hawaii
"Welcome to your serene oasis at Wailea Ekahi Village 42D, a meticulously designed 1-bedroom garden view condo that promises an unforgettable stay....
From $378/night
Palms at Wailea Villa 2203 Garden Deluxe 1 BD 2 BA
Wailea, Hawaii
Tucked within the world-famous Wailea resort community, this garden-view villa offers a serene retreat surrounded by tropical beauty. Enjoy a...
From $395/night
Elevated Ocean Views | Walk to the Beach
Wailea, Hawaii
Wailea Ekahi 47D is a spacious and beautifully updated one-bedroom, two-bath condo located in one of Wailea’s most sought-after beachfront...
From $396/night
Remodeled Ocean View | Wailea Ekolu 703
Wailea, Hawaii
Beautifully remodeled and thoughtfully appointed, this 2-bedroom, 2-bathroom ground-floor residence offers a sophisticated yet relaxed setting...
From $400/night
Sunset & Ocean Views | Fun Resort Amenities
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 49B Wake up to the open ocean and swaying palms — then step out to the private lanai,...
From $432/night
Beachfront 2BR condo in Wailea w/ pool and hot tub
Wailea, Hawaii
Welcome to Polo Beach Club 703, a beautifully positioned two-bedroom, two-bath residence in the exclusive beachfront Polo Beach Club in Wailea. This...