Wailea Grand Champion #90 Breathtaking Fairway Views & Serene Surroundings AwaitFrom $249/night · Sleeps 5
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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Map View · Page 17
Wailea Vacation Rentals Map
Wailea Grand Champion #90 Breathtaking Fairway Views & Serene Surroundings AwaitFrom $249/night · Sleeps 5
Bright Wailea Retreat with Pool Palms at Wailea 604From $685/night · Sleeps 8
Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And PalmsFrom $1,377/night · Sleeps 8
Tropical setting on the Wailea Blue Golf CourseFrom $173/night · Sleeps 6
Breathtaking Ocean Vistas Above the Fairway - Wailea Ekolu #312From $299/night · Sleeps 4
Tranquil Groundfloor Retreat - Wailea Ekolu Village 401 - Close to Pool & BBQ!From $428/night · Sleeps 6
Wailea Ekahi Village 50E - Relaxing Ocean and Mountain ViewsFrom $463/night · Sleeps 2
WEK 37C Getaway at Wailea Retreat w AC Pool Near Beach and Golf CourseFrom $175/night · Sleeps 4
🌺 Wailea Beachfront Escape — A One-of-a-Kind Hawaiian RetreatFrom $230/night · Sleeps 4
Wailea Ekolu Village 1406 | Gorgeous Views + Community Pool!From $404/night · Sleeps 4
Grand Champion Villa: Luxury Stay, Pool, Fast WiFiFrom $327/night · Sleeps 4
Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.From $195/night · Sleeps 4
Hidden Gem! Beautifully upgraded, Top floor! Palms at Wailea 2106From $188/night · Sleeps 4
Tranquil Ground-Floor Retreat: Wailea Elua 105, Set in an Enchanting PropertyFrom $854/night · Sleeps 6
Wailea Ekolu 1514 - Ocean Views, Private Lanais, Spacious 2-Story in Beautiful WaileaFrom $457/night · Sleeps 6
Unique Private Ocean View House With Pool - Walking Distance To Wailea ResortsFrom $199/night · Sleeps 9
Stunning Ground-Level Oasis W/ Breathtaking Oceanfront Views - Wailea Elua 1403From $1,651/night · Sleeps 4
Stay Longer, Save More at Palms at Wailea 1405From $279/night · Sleeps 6
Your Island Sanctuary: Spacious Ground-Floor Condo at Wailea Elua #2201From $1,298/night · Sleeps 6
Unforgettable Maui Escape: Experience Wailea Elua 1402, Your Oceanfront Haven!From $949/night · Sleeps 4
Wailea Ekahi 46F Paradise Found- Spacious 2 bedroom 2 Bath Condo in WaileaFrom $325/night · Sleeps 6
Spacious 2 bedroom 2 bath Palms at Wailea 1703From $195/night · Sleeps 6
Spacious Wailea Condo Near Beaches, Shops & RestaurantsFrom $399/night · Sleeps 6
GC 179 Relaxing 3Bedroom Wailea Condo w AC Pools Hot TubFrom $275/night · Sleeps 8
Beautifully Remodeled Wailea Condo Perfect for your Family VacationFrom $450/night · Sleeps 4
NEW!! Wailea Ekolu Ocean Suite 207 with AC and Ocean ViewsFrom $637/night · Sleeps 4
Elegant Wailea Retreat Near Keawakapu Beach & Resort AmenitiesFrom $152/night · Sleeps 6
Townhouse Retreat with Ocean Views From Upper & Lower Lanai - Wailea Ekahi #30BFrom $489/night · Sleeps 5
Grand Champion Villa Getaway - Wailea BeachesFrom $269/night · Sleeps 4
Exquisite Prime Beachfront Haven, Indulge in Tropical Luxury -Wailea Elua 1302From $858/night · Sleeps 4
Spectacular Views at Wailea Elua 2010: Tranquil Oasis on Lush Oceanfront GroundsFrom $851/night · Sleeps 6
Amazing Gem Nestled on Lush & Beachfront Grounds -Wailea Elua 2106From $919/night · Sleeps 6
Ground-Level Beauty on a Verdant Oceanfront Property - Wailea Elua 1601From $1,058/night · Sleeps 4
From $249/night
Wailea Grand Champion #90 Breathtaking Fairway Views & Serene Surroundings Await
Wailea, Maui, Hawaii
★★★★★ 9.4/10 · 5 reviews
Wailea Grand Champions #90 – Partial Ocean & Fairway Views in the Heart of WaileaEscape to the peaceful beauty of Wailea Grand Champions #90, a...
From $685/night
Bright Wailea Retreat with Pool Palms at Wailea 604
Kihei, Hawaii
★★★★★ 9.4/10 · 4 reviews
Experience the perfect blend of luxury and comfort in this beautifully updated 2-bedroom, 2-bathroom condo at the prestigious Palms at Wailea. This...
From $1,377/night
Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms
Wailea-Makena, Hawaii
★★★★★ 9.2/10 · 49 reviews
Features of our 3300 sq condo include: Two full master suites Second and Third bedroom can have two twins or king sized bedFourth Bedroom is queen...
From $173/night
Tropical setting on the Wailea Blue Golf Course
Kihei, Hawaii
★★★★★ 9.2/10 · 26 reviews
Ekolu 1602 is a 2-bedroom, 2-bathroom condo on the second floor featuring amenities such as three private lanais, air-conditioning, and a...
From $299/night
Breathtaking Ocean Vistas Above the Fairway - Wailea Ekolu #312
Wailea, Maui, Hawaii
★★★★★ 9.2/10 · 24 reviews
Wailea Ekolu #312 – Unforgettable Ocean Views & Island EleganceFind your private slice of paradise at Wailea Ekolu #312, a beautifully appointed...
From $428/night
Tranquil Groundfloor Retreat - Wailea Ekolu Village 401 - Close to Pool & BBQ!
Wailea, Maui, Hawaii
★★★★★ 9.2/10 · 21 reviews
Wailea Ekolu #401 – Your Ocean View Wailea RetreatSurround yourself with sunshine, palm trees, and endless ocean views at Wailea Ekolu #401. This...
From $463/night
Wailea Ekahi Village 50E - Relaxing Ocean and Mountain Views
Kihei, Hawaii
★★★★★ 9.2/10 · 18 reviews
Welcome to Wailea Ekahi 50E, our deluxe condo for two. We are on the 2nd (top) floor with beautiful ocean and garden views and wonderful tropical...
From $175/night
WEK 37C Getaway at Wailea Retreat w AC Pool Near Beach and Golf Course
Kihei, Hawaii
★★★★★ 9.2/10 · 15 reviews
Experience the Luxury of Wailea at Updated 1Bedroom Condo with Split AC Throughout and Comfortably Furnished and a Short Walk to South Maui...
From $230/night
🌺 Wailea Beachfront Escape — A One-of-a-Kind Hawaiian Retreat
Kihei, Hawaii
★★★★★ 9.2/10 · 10 reviews
This isn't your typical vacation rental. Unit 43C at Ekahi Village is a thoughtfully renovated, ground-floor condo decorated in rich Hawaiiana style...
From $404/night
Wailea Ekolu Village 1406 | Gorgeous Views + Community Pool!
Kihel, Hawaii
★★★★★ 9.2/10 · 10 reviews
Welcome to Wailea Ekolu Village 1406, your serene tropical oasis nestled in the heart of Kihei, Hawaii. This stunning condo offers a tranquil retreat...
From $327/night
Grand Champion Villa: Luxury Stay, Pool, Fast WiFi
Wailea-Makena, Hawaii
★★★★★ 9.2/10 · 8 reviews
Summary:🏖 Prime Location – Walk to beaches & top dining 🛏️ King Suite + Sofa Bed – Comfort & space for all 🌅 Private Lanai – Relax with poolside...
From $195/night
Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.
Kihei, Hawaii
★★★★★ 9.0/10 · 101 reviews
The tropical splendor surrounding Grand Champion Villas is a paradise. Wailea, near Kihei is where you can play 54 holes of championship golf and...
From $188/night
Hidden Gem! Beautifully upgraded, Top floor! Palms at Wailea 2106
Kihei, Hawaii
★★★★★ 9.0/10 · 69 reviews
Fabulous condo! This luxury, private unit is located on the top floor and has all the amenities this popular complex affords.This spacious 2 bedroom...
From $854/night
Tranquil Ground-Floor Retreat: Wailea Elua 105, Set in an Enchanting Property
Wailea-Makena, Hawaii
★★★★★ 9.0/10 · 11 reviews
Wailea Elua #105 – Ocean View Luxury and Secluded Serenity in the Heart of WaileaWelcome to Wailea Elua #105, a beautifully remodeled 2-bedroom,...
From $457/night
Wailea Ekolu 1514 - Ocean Views, Private Lanais, Spacious 2-Story in Beautiful Wailea
Kihei, Hawaii
★★★★★ 9.0/10 · 9 reviews
Welcome to Wailea Ekolu 1514 - a spacious, two-story luxury condo designed for travelers seeking comfort, privacy, and jaw-dropping ocean views. This...
From $199/night
Unique Private Ocean View House With Pool - Walking Distance To Wailea Resorts
Kihei, Hawaii
★★★★★ 9.0/10 · 2 reviews
Wailea Freedom House is pure and simple elegance in an unmatched location backing onto the Wailea Blue Golf Course. This home has a large heated...
From $1,651/night
Stunning Ground-Level Oasis W/ Breathtaking Oceanfront Views - Wailea Elua 1403
Kihei, Hawaii
★★★★★ 9.0/10 · 2 reviews
Wailea Elua #1403 is a stunning ocean-view retreat that blends contemporary elegance with Maui's relaxed beachfront charm. Completely rebuilt in...
From $279/night
Stay Longer, Save More at Palms at Wailea 1405
Kihei, Hawaii
★★★★★ 8.8/10 · 22 reviews
Escape to paradise in our luxurious ocean-view condo at the Palms at Wailea. Enjoy stunning sunsets, resort amenities, and the perfect Maui getaway...
From $1,298/night
Your Island Sanctuary: Spacious Ground-Floor Condo at Wailea Elua #2201
Kihei, Hawaii
★★★★★ 8.8/10 · 13 reviews
Wailea Elua #2201 – Spacious Island Comfort with Partial Ocean ViewsWelcome to Wailea Elua Village #2201, a beautifully upgraded ground-floor condo...
From $949/night
Unforgettable Maui Escape: Experience Wailea Elua 1402, Your Oceanfront Haven!
Wailea, Maui, Hawaii
★★★★★ 8.8/10 · 3 reviews
Wailea Elua #1402 – Oceanfront Luxury with Spectacular ViewsIf you're searching for an exceptional oceanfront condo on Maui, look no further than...
From $325/night
Wailea Ekahi 46F Paradise Found- Spacious 2 bedroom 2 Bath Condo in Wailea
Kihei, Hawaii
★★★★★ 8.6/10 · 46 reviews
Wailea Ekahi - Beautiful Garden and Ocean Views from this comforting unit! Nice 2 bedroom, 2 bath condo over looking the top pool area. Take pathways...
From $195/night
Spacious 2 bedroom 2 bath Palms at Wailea 1703
Kihei, Hawaii
★★★★★ 8.6/10 · 33 reviews
Book with us and come to Maui to explore everything we have to offer!Enjoy the beautiful lanai and grounds of the Palms at Wailea with this elegant...
From $399/night
Spacious Wailea Condo Near Beaches, Shops & Restaurants
Kihei, Hawaii
★★★★★ 8.6/10 · 33 reviews
Palms at Wailea 601 offers the perfect location in Wailea. This 2-bedroom/2-bath ground level unit surrounded by the lush landscaping makes this a...
From $275/night
GC 179 Relaxing 3Bedroom Wailea Condo w AC Pools Hot Tub
Kihei, Hawaii
★★★★★ 8.6/10 · 26 reviews
3Bedroom, 2Bathroom, Corner Unit Set Amidst the 18-Hole Wailea Blue Golf Course. Walk to 5-Star Resorts, Restaurants, and Luxury Shopping at the...
From $450/night
Beautifully Remodeled Wailea Condo Perfect for your Family Vacation
Kihei, Hawaii
★★★★★ 8.6/10 · 13 reviews
Hawaii Tax ID: TA-043-585-3312-01TMK: 210080770146Beautifully remodeled second floor unit is perfect for your family vacation. Nice and quiet...
From $637/night
NEW!! Wailea Ekolu Ocean Suite 207 with AC and Ocean Views
Kihei, Hawaii
★★★★★ 8.4/10 · 8 reviews
Welcome to Wailea Ekolu #207, a modern, newly renovated condo on the 10th hole of the Wailea Blue Course with a breathtaking 180° ocean view—perfect...
From $152/night
Elegant Wailea Retreat Near Keawakapu Beach & Resort Amenities
Kihei, Hawaii
★★★★★ 8.2/10 · 25 reviews
Top floor condo, #1302 overlooks the lush, landscaped grounds of Palms at Wailea out to a beautiful view of the Pacific Ocean. Watch whales breaching...
From $489/night
Townhouse Retreat with Ocean Views From Upper & Lower Lanai - Wailea Ekahi #30B
Wailea, Maui, Hawaii
★★★★★ 8.0/10 · 6 reviews
Wailea Ekahi Village #30B Discover the perfect blend of luxury, comfort, and location at Wailea Ekahi Village #30B. This spacious two-story townhouse...
From $269/night
Grand Champion Villa Getaway - Wailea Beaches
Wailea-Makena, Hawaii
★★★★★ 8.0/10 · 2 reviews
Summary:🌴 Prime Location – Walk to beach, dining & shops🌅 Tranquil Balcony – Enjoy morning coffee w/ lush views 💤 Luxury Beds & Linens – Ultimate...
From $858/night
Exquisite Prime Beachfront Haven, Indulge in Tropical Luxury -Wailea Elua 1302
Wailea, Maui, Hawaii
★★★★★ 8.0/10 · 2 reviews
Wailea Elua #1302 – Premier Beachfront One-Bedroom Escape in the Heart of WaileaWelcome to Wailea Elua #1302, a luxurious 1-bedroom, 1-bathroom...
From $851/night
Spectacular Views at Wailea Elua 2010: Tranquil Oasis on Lush Oceanfront Grounds
Wailea, Maui, Hawaii
★★★★★ 7.8/10 · 20 reviews
Wailea Elua #2010 – Elevated Island Comfort with Panoramic ViewsEnjoy the perfect blend of comfort and convenience at Wailea Elua #2010, a...
From $919/night
Amazing Gem Nestled on Lush & Beachfront Grounds -Wailea Elua 2106
Wailea, Maui, Hawaii
★★★★★ 7.4/10 · 9 reviews
Wailea Elua #2106 – Elevated Island Comfort with Ocean & Village ViewsWelcome to Wailea Elua #2106, a beautifully updated second-floor condo offering...
From $1,058/night
Ground-Level Beauty on a Verdant Oceanfront Property - Wailea Elua 1601
Wailea-Makena, Hawaii
★★★★★ 6.6/10 · 5 reviews
Wailea Elua #1601 – Oceanfront Luxury with Upgraded Interior & Ground Floor AccessStep into effortless island living at Wailea Elua #1601, a...