Grand Champions Villas 156 - Ocean & Golf Course View, King Size BedFrom $450/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
Grand Champions Villas 156 - Ocean & Golf Course View, King Size BedFrom $450/night · Sleeps 4
#21B Grand Champions Studio -Ulua & Mokapu beachesFrom $175/night · Sleeps 2
Tranquil Garden Oasis Steps from Oceanfront Pool & Ulua Beach - Elua 909From $620/night · Sleeps 4
Mana Kai Kihei condo w/ private lanai, pool access, summer dealFrom $730/night · Sleeps 6
Ekahi Village 44C - Beautifully appointed Ocean View Condo mins from the beachFrom $342/night · Sleeps 4
Sweet Studio Whaler #813, Romantic Ocean ViewsFrom $217/night · Sleeps 2
New! Palms 702 - Romantic Retreat - Split AC in Bedroom - Open-Air Living AreaFrom $361/night · Sleeps 4
Save 25% Instantly from 04/06/25-04/15/25! Grand Champions 61! 2B/2B, AC, Slps 8From $312/night · Sleeps 8
Cozy, Well-Furnished StudioFrom $198/night · Sleeps 2
Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112From $220/night · Sleeps 4
#21A Grand Champions 1 Bed - Ulua & Mokapu beachesFrom $214/night · Sleeps 3
SUMMER SALE! Experience luxury in a spacious 2BR Stunning Ocean views- WE 1106From $273/night · Sleeps 6
Luxury Penthouse w/ ocean views and poolFrom $2,196/night · Sleeps 6
Beachfront condo w/ ocean views and 4 resort poolsFrom $179/night · Sleeps 2
From $450/night
Grand Champions Villas 156 - Ocean & Golf Course View, King Size Bed
Kihei, Hawaii
★★★★★ 9.6/10 · 31 reviews
We are located in the heart of Wailea at the Grand Champions Villas, close to Maui's best beaches and within walking distance to great restaurants,...
From $175/night
#21B Grand Champions Studio -Ulua & Mokapu beaches
Kihei, Hawaii
★★★★★ 9.6/10 · 26 reviews
Located in the heart of Wailea. Grand Champions is a 4-star world class resort that features two pools with whirlpool spas, BBQ facilities, and...
From $620/night
Tranquil Garden Oasis Steps from Oceanfront Pool & Ulua Beach - Elua 909
Wailea, Maui, Hawaii
★★★★★ 9.6/10 · 17 reviews
Wailea Elua #909 – Garden View Comfort Just Steps from the Pavilion, Pool, and BeachWelcome to Wailea Elua #909, a charming 1-bedroom, 1-bathroom...
From $730/night
Mana Kai Kihei condo w/ private lanai, pool access, summer deal
Kihei, Hawaii
★★★★★ 9.6/10 · 6 reviews
Come stay on one of the most popular beaches in Hawaii! Mana Kai Resort is situated on Keawakapu beach and faces South, perfectly blocking the North...
From $342/night
Ekahi Village 44C - Beautifully appointed Ocean View Condo mins from the beach
Kihei, Hawaii
★★★★★ 9.4/10 · 85 reviews
Wailea Ekahi Village 44C is a lovely and romantic two-story townhouse. The downstairs lanai is surrounded by lush gardens with the sweet aroma of...
From $217/night
Sweet Studio Whaler #813, Romantic Ocean Views
Lahaina, Hawaii
★★★★★ 9.4/10 · 35 reviews
The Whaler is an ocean front resort located next to Whalers Village. This gorgeous studio located on the 8th floor in Tower I, has views of the West...
From $361/night
New! Palms 702 - Romantic Retreat - Split AC in Bedroom - Open-Air Living Area
Kihei, Hawaii
★★★★★ 9.4/10 · 26 reviews
* * * * The Palms at Wailea Pool Area will be Closed for Annual Maintenance Tuesday, Sept,. 15th through Friday, Sept,.18th 2026. The Pool Area Will...
From $312/night
Save 25% Instantly from 04/06/25-04/15/25! Grand Champions 61! 2B/2B, AC, Slps 8
Kihei, Hawaii
★★★★★ 9.4/10 · 16 reviews
Nestled in the prestigious Wailea Resort community, Grand Champions Villas 61 offers a prime retreat with breathtaking views of the Wailea Blue Golf...
From $198/night
Cozy, Well-Furnished Studio
Kihei, Hawaii
★★★★★ 9.0/10 · 70 reviews
Relax, enjoy the gentle breeze, take a deep breath and enjoy the birds, flowers and scents of Maui that surround you. Our quiet location is...
From $220/night
Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112
Kihei, Hawaii
★★★★★ 9.0/10 · 9 reviews
Book with us and come to Maui to explore everything we have to offer!This spacious Wailea Grand Champions Villas 2 bedroom 2 bath second floor unit...
From $214/night
#21A Grand Champions 1 Bed - Ulua & Mokapu beaches
Kihei, Hawaii
★★★★★ 9.0/10 · 7 reviews
Welcome to our spacious ground floor condo with a tropical garden view.Located in the heart of Wailea. Grand Champions is a world class resort...
From $273/night
SUMMER SALE! Experience luxury in a spacious 2BR Stunning Ocean views- WE 1106
Kihei, Hawaii
★★★★★ 36 reviews
FLASH SUMMER SALE! We're offering exclusive discounts on all summer stays booked this week—don't miss out on these updated lower rates.Wailea Ekolu...
From $2,196/night
Luxury Penthouse w/ ocean views and pool
Kihei, Hawaii
★★★★★ 4 reviews
Wailea Beach Villas has been ranked #4 in Hawaii by Condé Nast Readers. This recognition places WBV among the very best resorts in Hawaii, and the...
From $179/night
Beachfront condo w/ ocean views and 4 resort pools
Wailea-Makena, Hawaii
★★★★★ 2 reviews
Experience this elegant one-bedroom, two-bathroom retreat set within the highly sought-after Wailea Ekahi Village in Wailea. Surrounded by 34 acres...