Golf + Partial Ocean Views - Grand Champions 71From $344/night · Sleeps 4
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
Golf + Partial Ocean Views - Grand Champions 71From $344/night · Sleeps 4
Tiki Tiki - A Gorgeous Boho Beach Hideaway!From $625/night · Sleeps 2
Sunset Ocean Views | Whale Watching | Wailea Ekahi 38BFrom $672/night · Sleeps 4
Walk to Waves, Snorkeling, & RestaurantsFrom $868/night · Sleeps 4
Wailea Villa in Top-Rated Hawaii ResortFrom $1,080/night · Sleeps 6
Exceptional Design & Ocean ViewsFrom $1,084/night · Sleeps 6
Wailea Beach Villas PH502 - Professionally ManagedFrom $1,129/night · Sleeps 6
KBM Resorts | FREE CAR | Wailea Beach Villa | Spacious 3-Bedroom Condo with Sweeping Ocean view! WBV-PH 412From $1,529/night · Sleeps 6
Spacious Condo - Great for FamiliesFrom $2,043/night · Sleeps 8
Golfer's Dream | Condo on Wailea CourseFrom $216/night · Sleeps 4
Stylish Beach Studio - Professional ManagedFrom $276/night · Sleeps 2
Spacious Condo on Favorite Local BeachFrom $348/night · Sleeps 4
Wailea Grand Champions 152 | Golf & Ocean Views, Whales Sighting & Resort PoolsFrom $358/night · Sleeps 4
Recently Renovated Ocean View - Platinum RatedFrom $501/night · Sleeps 4
Wailea Elua 2004 | Hot tub | Pool | Sunset ViewsFrom $833/night · Sleeps 4
Tropical Ocean & Pool ViewsFrom $1,085/night · Sleeps 6
Panoramic Ocean Views - Wailea Beach Villas PH406From $1,113/night · Sleeps 6
Walk to Wailea Waves, Snorkeling, RestaurantsFrom $1,150/night · Sleeps 6
Wailea Elua Village 1102 | Nicely Remodeled, Ocean Views & Walk to Ulua BeachFrom $1,183/night · Sleeps 4
Spacious Condo on Top Snorkeling BeachFrom $1,269/night · Sleeps 6
Wailea Elua Village 1604 | Oceanfront, Renovated, 1 Min to Ulua BeachFrom $1,681/night · Sleeps 4
Spacious Wailea Condo - Professionally Managed - Ekolu 1607From $196/night · Sleeps 4
Spacious Condo on Favorite Local BeachFrom $217/night · Sleeps 4
Wailea Grand Champions 183 | Ground Floor, Resort Pools & Walk to WaileaFrom $232/night · Sleeps 6
Wailea Grand Champions 43 | Golf, Tennis, Resort Pools & 5-Min Walk to WaileaFrom $278/night · Sleeps 6
Golf + Partial Ocean Views - Grand Champions 73From $315/night · Sleeps 4
Wailea Ekahi Village 39A | Garden Views, Private Lanai Grill & Beach AccessFrom $335/night · Sleeps 4
Wailea Ekahi Village 54D | Sweeping Ocean Views, Updated Kitchen & Resort PoolsFrom $451/night · Sleeps 4
Wailea Ekahi Village 10F | Tropical Garden Views, Resort Pools & Beach AccessFrom $474/night · Sleeps 4
Wailea Ekahi Village 7B | Spacious Garden Retreat, 1-min Walk to Pool & BeachFrom $481/night · Sleeps 4
Wailea Ekahi Village 34E | Spacious Ocean View Condo & Beach AccessFrom $482/night · Sleeps 4
Palms at Wailea Villa 806 Ocean View 2BD 2BAFrom $508/night · Sleeps 5
Ocean View Stunner - Professionally Managed - Elua 2402From $811/night · Sleeps 4
From $344/night
Golf + Partial Ocean Views - Grand Champions 71
Wailea, Hawaii
★★★★★ 10.0/10 · 3 reviews
Wailea Grand Champions 71 is a beautifully updated ground-floor vacation rental that offers both fairway and ocean views from the living room and...
From $625/night
Tiki Tiki - A Gorgeous Boho Beach Hideaway!
Wailea, Hawaii
★★★★★ 10.0/10 · 3 reviews
Fall in ALOHA with Tiki Tiki!! This special studio is truly a piece of Paradise! A magical retreat that will have you feeling zen & refreshed. Tiki...
From $672/night
Sunset Ocean Views | Whale Watching | Wailea Ekahi 38B
Wailea, Hawaii
★★★★★ 10.0/10 · 3 reviews
Enjoy a relaxing indoor/outdoor tropical vacation experience from this ground floor ocean view vacation rental. Start your morning on the lanai with...
From $868/night
Walk to Waves, Snorkeling, & Restaurants
Wailea, Hawaii
★★★★★ 10.0/10 · 3 reviews
Wailea Elua Village 2012 is a luxurious vacation rental located in the stunning Wailea area of Maui. This one-bedroom, two-bathroom condo offers an...
From $1,080/night
Wailea Villa in Top-Rated Hawaii Resort
Wailea, Hawaii
★★★★★ 10.0/10 · 3 reviews
Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms...
From $1,084/night
Exceptional Design & Ocean Views
Wailea, Hawaii
★★★★★ 10.0/10 · 3 reviews
Settle into your very own slice of Maui paradise with a stay in Wailea Beach Villas PH306. This exquisite two bedroom, two bathroom penthouse with...
From $1,129/night
Wailea Beach Villas PH502 - Professionally Managed
Wailea, Hawaii
★★★★★ 10.0/10 · 3 reviews
Wailea Beach Villas Penthouse 502 boasts a panoramic ocean vista, ideal for whale watching in the winter, and with spectacular sunset views all year...
From $1,529/night
KBM Resorts | FREE CAR | Wailea Beach Villa | Spacious 3-Bedroom Condo with Sweeping Ocean view! WBV-PH 412
Wailea, Hawaii
★★★★★ 10.0/10 · 3 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 $2,043/night
Spacious Condo - Great for Families
Wailea, Hawaii
★★★★★ 10.0/10 · 3 reviews
The Wailea Elua 804 vacation rental is a true gem nestled within the picturesque Wailea resort community on the island of Maui. From the moment you...
From $216/night
Golfer's Dream | Condo on Wailea Course
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
Villa 104 at Wailea Grand Champions Villas is a beautiful Maui vacation rental that offers an exceptional blend of style, comfort, and convenience....
From $276/night
Stylish Beach Studio - Professional Managed
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
Wailea Ekahi 4D is a charming studio vacation rental perfect for the couple or solo traveler. This second-floor unit offers an elevated retreat with...
From $348/night
Spacious Condo on Favorite Local Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
Wailea Ekahi 3E is a charming one-bedroom vacation rental located in the picturesque Wailea Ekahi Village. Situated on the second floor, this condo...
From $358/night
Wailea Grand Champions 152 | Golf & Ocean Views, Whales Sighting & Resort Pools
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 152Wailea Grand Champions is an 11-acre country club-style resort set along the...
From $501/night
Recently Renovated Ocean View - Platinum Rated
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
Make your Maui dreams come true at Wailea Ekahi 35D! This vacation rental is perched on the top floor with a private entrance surrounded by manicured...
From $833/night
Wailea Elua 2004 | Hot tub | Pool | Sunset Views
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
Wailea Elua 2004 is a luxurious vacation rental located along the shores of Maui\'s southern coastline. This one-bedroom, one-bathroom condominium...
From $1,085/night
Tropical Ocean & Pool Views
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
In Wailea Beach Villas PH307 you can immerse yourself in luxe tropical comforts blended with blue ocean views. This delightful Maui ocean view...
From $1,113/night
Panoramic Ocean Views - Wailea Beach Villas PH406
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
Wailea Beach Villas Penthouse 406 is desirable for its remarkable Pacific Ocean and Island views. This upscale penthouse vacation rental features two...
From $1,150/night
Walk to Wailea Waves, Snorkeling, Restaurants
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
Call this private piece of paradise home, which features panoramic views of Maui and the ocean below as well as luxurious interior elements...
From $1,183/night
Wailea Elua Village 1102 | Nicely Remodeled, Ocean Views & Walk to Ulua Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1102 Elua Village sits steps from Ulua Beach and connects directly to the 3.2-mile...
From $1,269/night
Spacious Condo on Top Snorkeling Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
Wailea Elua Village 708 is a luxurious two-bedroom, two-bathroom vacation rental located in the prestigious Wailea community on Maui\'s southern...
From $1,681/night
Wailea Elua Village 1604 | Oceanfront, Renovated, 1 Min to Ulua Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 2 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1604Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $196/night
Spacious Wailea Condo - Professionally Managed - Ekolu 1607
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
Wailea Ekolu 1607 is a stunning one-bedroom, two-bathroom vacation rental that offers an exceptional escape in beautiful Wailea. This beautifully...
From $217/night
Spacious Condo on Favorite Local Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
Wailea Ekahi 35C is a stunning vacation rental located in the desirable Wailea community. This beautifully appointed one-bedroom, one-bathroom condo...
From $232/night
Wailea Grand Champions 183 | Ground Floor, Resort Pools & Walk to Wailea
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 183Wailea Grand Champions is an 11-acre country club-style resort set along the...
From $278/night
Wailea Grand Champions 43 | Golf, Tennis, Resort Pools & 5-Min Walk to Wailea
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 43Wailea Grand Champions is an 11-acre country club-style resort set along the...
From $315/night
Golf + Partial Ocean Views - Grand Champions 73
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 73Wailea Grand Champions sits along the Wailea Blue Golf Course, next door to the...
From $335/night
Wailea Ekahi Village 39A | Garden Views, Private Lanai Grill & Beach Access
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
A short distance from birdwatching, wildlife walks, and more, this smoke-free condo lets you experience it all. Shops at Wailea is within an easy...
From $451/night
Wailea Ekahi Village 54D | Sweeping Ocean Views, Updated Kitchen & Resort Pools
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 54D Picture your evening: golden Maui sunsets lighting up the Pacific from the...
From $474/night
Wailea Ekahi Village 10F | Tropical Garden Views, Resort Pools & Beach Access
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 10FNestled inside 34 acres of lush botanical gardens, a short walk from Keawakapu...
From $481/night
Wailea Ekahi Village 7B | Spacious Garden Retreat, 1-min Walk to Pool & Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 7BA spacious 1,160 sq.ft. 1-bedroom ground-floor condo with 2 full bathrooms,...
From $482/night
Wailea Ekahi Village 34E | Spacious Ocean View Condo & Beach Access
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 34E At 1,180 square feet, Wailea Ekahi Village 34E is one of the most spacious...
From $508/night
Palms at Wailea Villa 806 Ocean View 2BD 2BA
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
This two-bedroom villa boasts stunning ocean vistas and a tranquil setting within Wailea’s resort community. With a full kitchen, comfortable living...
From $811/night
Ocean View Stunner - Professionally Managed - Elua 2402
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
Wailea Elua Village 2402 is an exquisite ocean-view second-floor condo located in the prestigious Wailea area of Maui. This elevated condo with...