Wailea Ekahi 10C - Just steps away from Main Pool & Beach! - Family ManagedFrom $539/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
Wailea Ekahi 10C - Just steps away from Main Pool & Beach! - Family ManagedFrom $539/night · Sleeps 4
Steps to Beach. Stunning View. Lovely 2BR Condo near WaileaFrom $689/night · Sleeps 6
Discount Week Rates! Elua Premier 2-Bedroom Front-Row... Oceanfront Unit!From $1,666/night · Sleeps 4
Palms at Wailea Spectacular Ocean Views with Exceptional Star RatingFrom $390/night · Sleeps 6
Wailea Ekahi 54C: Best View/New Kitchen Paint and Refresh September 2026!From $563/night · Sleeps 6
Beautiful Wailea Ekolu Townhouse- Spectacular View- Your Perfect Maui Get-AwayFrom $704/night · Sleeps 6
Hawaiian Reno on Wailea Blue Golf *Ocean View*PoolFrom $379/night · Sleeps 6
Steps to Kamaole beaches/Upgraded kitchen & baths/2 Pools/Tennis/Close to WaileaFrom $423/night · Sleeps 5
Maui's Best - Wailea Ekahi 47AFrom $454/night · Sleeps 4
Stunning Ocean Front Views, Wailea, Polo Beach Club Condo - unit 303From $1,268/night · Sleeps 6
16B; Ocean View, Quiet Beachfront King Studio in Luxurious Wailea Ekahi ResortFrom $404/night · Sleeps 2
Luxury Condo in Wailea with sweeping viewsFrom $550/night · Sleeps 5
Spectacular Panoramic Ocean Views - Private Ohana - Wailea Custom Pole HomeFrom $575/night · Sleeps 5
Stunning 2-bedroom Wailea Elua, walk to beach, ocean view!From $405/night · Sleeps 6
New Listing, Wailea Ekahi 4A, Close to Best Beaches, Shops of Wailea & World Class GolfFrom $452/night · Sleeps 6
Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach accessFrom $499/night · Sleeps 6
Sandy Beach Front Property - Family Friendly - 4 min stroll to H2O - Ocean ViewsFrom $791/night · Sleeps 6
Grand Champions 105 I Spacious Wailea 3bdFrom $550/night · Sleeps 8
Wailea Beach Villas E-302 on Wailea BeachFrom $2,400/night · Sleeps 8
Private Ocean View Cottage Overlooking WaileaFrom $261/night · Sleeps 4
Newly Renovated High-end 1 bedroom, 2 bathroom Wailea Condo close to beachFrom $484/night · Sleeps 4
Wailea Ekahi 24B, 1BR Ground-Floor Condo with 2 Baths, Split AC, Pool, Sleeps 4From $502/night · Sleeps 4
Modern Spacious Beachfront Luxury in Wailea. Family Friendly!From $675/night · Sleeps 6
Receive a $100 Gift Card for Snorkel Gear or Wailea Dining Options!From $199/night · Sleeps 6
Fantastic Beachfront Wailea Ekahi 2/2 43AFrom $649/night · Sleeps 6
Luxury Oceanfront 2-Bedroom Condo with Sunset Views | Polo Beach Club #707, Wailea-MakenaFrom $1,249/night · Sleeps 4
Wailea 2BR Condo-GC100. Golf Course View. Full AC. Walk to Shops & BeachesFrom $209/night · Sleeps 6
WE 907 Breathtaking Ocean Views from the Top of Wailea 2BD Amazing LocationFrom $257/night · Sleeps 6
180 Degree Ocean View in Wailea! WE204From $314/night · Sleeps 5
Ground-Floor Gem in Wailea Ekahi VillageFrom $371/night · Sleeps 4
Close to Everything, Stunning Palms at Wailea Condo, Full A/C, Upper FloorFrom $408/night · Sleeps 6
Luxurious Wailea Ocean VistasFrom $604/night · Sleeps 4
Wailea Luxury Resort VistaFrom $581/night · Sleeps 4
From $539/night
Wailea Ekahi 10C - Just steps away from Main Pool & Beach! - Family Managed
Kihei, Hawaii
★★★★★ 10.0/10 · 59 reviews
Note: The main pool is closed for repairs until October 17th. The adjacent main pavilion is not closed. Unit 10C is very close to one of the other...
From $689/night
Steps to Beach. Stunning View. Lovely 2BR Condo near Wailea
Kihei, Hawaii
★★★★★ 10.0/10 · 54 reviews
Enjoy paradise at one of Maui's premier beaches. Our air-conditioned retreat features a clean, bright interior and stunning views from the main...
From $1,666/night
Discount Week Rates! Elua Premier 2-Bedroom Front-Row... Oceanfront Unit!
Kihei, Hawaii
★★★★★ 10.0/10 · 50 reviews
Ulua Beach Premier 2-Bedroom Oceanfront Unit...Unobstructed Ocean Views!Welcome to Wailea Ulua #1002! This recently renovated luxury beachfront 2...
From $390/night
Palms at Wailea Spectacular Ocean Views with Exceptional Star Rating
Kihei, Hawaii
★★★★★ 10.0/10 · 42 reviews
Aloha and welcome to our retreat in Wailea, Maui, the heart of paradise. Your Hawaiian vacation will be nothing short of spectacular when you stay in...
From $563/night
Wailea Ekahi 54C: Best View/New Kitchen Paint and Refresh September 2026!
Kihei, Hawaii
★★★★★ 10.0/10 · 42 reviews
Our Family owns 2 - Two bedroom units above and below each other in Ekahi Village. This is perfect for large Family vacations or groups of friends...
From $704/night
Beautiful Wailea Ekolu Townhouse- Spectacular View- Your Perfect Maui Get-Away
Kihei, Hawaii
★★★★★ 10.0/10 · 40 reviews
Welcome to Happy Everything!10 Wailea Ekolu Complex!A premier, fully re-modeled, well appointed and comfortable 2-story townhouse situated on hole 10...
From $379/night
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 38 reviews
BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea...
From $423/night
Steps to Kamaole beaches/Upgraded kitchen & baths/2 Pools/Tennis/Close to Wailea
Kihei, Hawaii
★★★★★ 10.0/10 · 38 reviews
This second floor 2 bedroom/2 bath peek-a-boo ocean view condo is your perfect Maui vacation retreat just across the street from beautiful Kamaole...
From $454/night
Maui's Best - Wailea Ekahi 47A
Kihei, Hawaii
★★★★★ 10.0/10 · 38 reviews
Aloha and mahalo for your interest in our spot in Paradise. Ekahi says it all. This one bedroom (with comfortable sleeper sofa), two-bath renovated...
From $1,268/night
Stunning Ocean Front Views, Wailea, Polo Beach Club Condo - unit 303
Kihei, Hawaii
★★★★★ 10.0/10 · 31 reviews
Welcome to your tropical escape at Polo Beach Club, our cherished slice of paradise! Having fallen in love with this magical location years ago, we...
From $404/night
16B; Ocean View, Quiet Beachfront King Studio in Luxurious Wailea Ekahi Resort
Kihei, Hawaii
★★★★★ 10.0/10 · 30 reviews
Ocean View, King Bed, quiet Ground floor Studio condo, in the beautiful Wailea Ekahi Resort, near one of the 4 private pools and a short walk to the...
From $550/night
Luxury Condo in Wailea with sweeping views
Kihei, Hawaii
★★★★★ 10.0/10 · 30 reviews
2 large master ensuite bedrooms with Cal King beds. Sweeping views of Kaho'olawe, Molokini, and Lanai islands and spectacular sunsets. Beaches,...
From $575/night
Spectacular Panoramic Ocean Views - Private Ohana - Wailea Custom Pole Home
Kihei, Hawaii
★★★★★ 10.0/10 · 29 reviews
Live like a local at the Ocean Blue Ohana. You'll have the entire private first floor of this amazing Hawaiian pole home on a half acre property in...
From $405/night
Stunning 2-bedroom Wailea Elua, walk to beach, ocean view!
Kihei, Hawaii
★★★★★ 10.0/10 · 28 reviews
August 17 - November 13, 2026 - Next door unit remodel, prices adjusted and as is:- August 17- 21 - loudest portion, demo- August 21 - September 4,...
From $452/night
New Listing, Wailea Ekahi 4A, Close to Best Beaches, Shops of Wailea & World Class Golf
Kihei, Hawaii
★★★★★ 10.0/10 · 21 reviews
Summary:Lovely, Spacious Maui Townhouse: Steps from Keawakapu Beach!The Space:Maintenance Notice: Our beach front pool will be closed from Monday,...
From $499/night
Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access
Kihei, Hawaii
★★★★★ 10.0/10 · 21 reviews
IMPORTANT NOTICE: Pavilion Pool Deck resurfacing Project - August 10 to October 16, 2026.The pavilion facilities WILL be available, including...
From $791/night
Sandy Beach Front Property - Family Friendly - 4 min stroll to H2O - Ocean Views
Kihei, Hawaii
★★★★★ 10.0/10 · 20 reviews
Experience the gold standard of Maui living at Wailea Ekahi 35B. This impeccably remodeled, 5-star oceanfront townhome offers breathtaking views from...
From $550/night
Grand Champions 105 I Spacious Wailea 3bd
Kihei, Hawaii
★★★★★ 10.0/10 · 19 reviews
Hawaii Life Vacations proudly presents Grand Champions #105, a beautifully updated 3-bedroom condo located in a serene corner of Grand Champions...
From $2,400/night
Wailea Beach Villas E-302 on Wailea Beach
Kihei, Hawaii
★★★★★ 10.0/10 · 17 reviews
Modern living, in one of the best locations at Wailea Beach Villas, with outer island and sunset views that are unmatched. Centrally located in the...
From $261/night
Private Ocean View Cottage Overlooking Wailea
Kihei, Hawaii
★★★★★ 10.0/10 · 13 reviews
Couples find the privacy and space they dream of in our 1-bedroom ocean view cottage set on a hillside in sunny south Maui. Our cottage offers a...
From $484/night
Newly Renovated High-end 1 bedroom, 2 bathroom Wailea Condo close to beach
Kihei, Hawaii
★★★★★ 10.0/10 · 13 reviews
The Palms at Wailea #1804 has been completely renovated, be among the first to enjoy this brand-new high-end renovation in Wailea in which every room...
From $502/night
Wailea Ekahi 24B, 1BR Ground-Floor Condo with 2 Baths, Split AC, Pool, Sleeps 4
Kihei, Hawaii
★★★★★ 10.0/10 · 11 reviews
* * * * The Wailea Ekahi main pool area will be closed for renovations from August 10, 2026 to October 15, 2026. The 3 other pools on property will...
From $675/night
Modern Spacious Beachfront Luxury in Wailea. Family Friendly!
Kihei, Hawaii
★★★★★ 10.0/10 · 11 reviews
A modern 2 bedroom, 2 bath condo with extra bunk beds and an amazing ocean view!South Maui is one of the most beautiful destinations in all of Maui...
From $199/night
Receive a $100 Gift Card for Snorkel Gear or Wailea Dining Options!
Kihei, Hawaii
★★★★★ 10.0/10 · 10 reviews
*Absolutely Stunning Panoramic Ocean and Island Views*Yards Away from Local Favorite Shops and Dining*4 beaches within 1-2 miles (Wailea, Ulua,...
From $649/night
Fantastic Beachfront Wailea Ekahi 2/2 43A
Kihei, Hawaii
★★★★★ 10.0/10 · 10 reviews
Welcome to my sunny Wailea Ekahi Paradise! This unit is a remodeled, expanded and wonderfully furnished 2 bedroom 2 bathroom ground-floor condo (Unit...
From $1,249/night
Luxury Oceanfront 2-Bedroom Condo with Sunset Views | Polo Beach Club #707, Wailea-Makena
Makena, Maui, Hawaii
★★★★★ 10.0/10 · 9 reviews
Polo Beach #707Indulge in the refined elegance of Polo Beach #707, a fully remodeled “Maui Modern Masterpiece” at the exclusive Polo Beach Club in...
From $209/night
Wailea 2BR Condo-GC100. Golf Course View. Full AC. Walk to Shops & Beaches
Kihei, Hawaii
★★★★★ 10.0/10 · 7 reviews
Your Maui vacation should be exciting and stress-free from the moment you book. We Make Booking Easy!>Flexibility: Plans change, life takes turns....
From $257/night
WE 907 Breathtaking Ocean Views from the Top of Wailea 2BD Amazing Location
Kihei, Hawaii
★★★★★ 10.0/10 · 7 reviews
Panoramic 2-bed ocean-view condo at Wailea Ekolu Village for the ultimate Maui stay-Wailea Ekolu 907Welcome to your Maui Retreat: Discover the luxury...
From $314/night
180 Degree Ocean View in Wailea! WE204
Kihei, Hawaii
★★★★★ 10.0/10 · 7 reviews
Welcome to Wailea Ekolu Village, unit 204! This is a top floor, FRONT LINE, two bed, two bath condo with a 180 degree ocean view! Overlooking the...
From $371/night
Ground-Floor Gem in Wailea Ekahi Village
Kihei, Hawaii
★★★★★ 10.0/10 · 7 reviews
Discover true island elegance in this beautifully updated ground-floor residence at Wailea Ekahi Village, one of Maui’s most sought-after beachfront...
From $408/night
Close to Everything, Stunning Palms at Wailea Condo, Full A/C, Upper Floor
Kihei, Hawaii
★★★★★ 10.0/10 · 7 reviews
Welcome to Palms at Wailea 2304. Come to Wailea to enjoy the most beautiful beaches and best restaurants Maui has to offer. Get ready to make...
From $604/night
Luxurious Wailea Ocean Vistas
Kihei, Hawaii
★★★★★ 10.0/10 · 7 reviews
Summary:Completely remodeled. Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor,...
From $581/night
Wailea Luxury Resort Vista
Kihei, Hawaii
★★★★★ 10.0/10 · 6 reviews
Summary:Completely remodeled. Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor,...