Wailea Condo with Private Lanai, Pool & Minutes to Keawakapu BeachFrom $225/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
Wailea Condo with Private Lanai, Pool & Minutes to Keawakapu BeachFrom $225/night · Sleeps 6
Wrap-Around Beach & Ocean Views | Polo Beach 301From $1,397/night · Sleeps 6
Polo Beach Club 409 | Ocean View Lanai, Beachfront Pool & Direct Beach AccessFrom $1,046/night · Sleeps 6
Oceanfront Polo Beach 407 - Professionally ManagedFrom $1,078/night · Sleeps 6
Floor to Ceiling Ocean Views - Wailea Elua 2006From $1,541/night · Sleeps 7
Recently Renovated - Walk to the BeachFrom $424/night · Sleeps 4
Wailea Elua Village 1301 | Front Row to the Ocean, Sunset Views & Steps to UluaFrom $871/night · Sleeps 4
Elevated Beachfront Views - Wailea Elua 1704From $1,169/night · Sleeps 6
Penthouse Retreat Walk to Wailea BeachFrom $2,107/night · Sleeps 6
3BD Wailea Villa - Great for Families | Wailea Beach Villas PH309From $2,880/night · Sleeps 8
Watch the Golfers Play ThroughFrom $216/night · Sleeps 4
Wailea Ekahi Village 12C - 1 Bedroom Ocea View CondoFrom $291/night · Sleeps 4
Recent Renovation - Close to Golf & DiningFrom $394/night · Sleeps 6
Beachfront Condo with Postcard Views - Makena Surf F306From $1,069/night · Sleeps 6
Wailea Elua Village 1703 | Oceanfront, Step-Free Walkout, 1 Min to BeachFrom $1,585/night · Sleeps 6
Conde Nast Award Winning Property - Wailea Beach Villas E202From $1,667/night · Sleeps 8
Stunning ocean view! 2/2 in the heart of WaileaFrom $329/night · Sleeps 5
Ocean Views | Tropical Decor | Professionally ManagedFrom $511/night · Sleeps 6
Newly Remodeled-Quiet Location-Ac-Well Equipped-Meticulous CleaningFrom $552/night · Sleeps 8
Wailea Elua Village 910 | Remodeled, Vaulted Ceilings, 2 Min to Ulua Beach and PFrom $776/night · Sleeps 4
Recently Renovated - Steps from SnorkelingFrom $1,077/night · Sleeps 6
Beachfront Condo – Hear the Waves Crash | Makena Surf C207From $1,182/night · Sleeps 6
Recently Renovated & Professionally Managed Ocean View VillaFrom $2,117/night · Sleeps 8
Recently Renovated | Wrap-Around Ocean Views | Wailea Beach Villas D302From $2,489/night · Sleeps 8
Golfer's Dream | Condo on Wailea CourseFrom $237/night · Sleeps 6
Wailea Ekahi Village 29D | Ocean Views, Resort Pools & Walkable LocationFrom $523/night · Sleeps 4
Prime Location | Snorkeling | Wailea Beach PathFrom $686/night · Sleeps 2
Wailea Ocean Views | Great for FamiliesFrom $897/night · Sleeps 6
Bright & Colorful Ocean View Villa | Wailea Beach Villas PH402From $2,061/night · Sleeps 4
Oceanfront 3BR villa w/ private lanai and Wailea Beach accessFrom $3,541/night · Sleeps 8
Wailea Grand Champions 111 | Tennis Views, Resort Pools & Walk to Wailea ShopsFrom $220/night · Sleeps 6
Ocean Views | Close to Wailea Golf & BeachesFrom $246/night · Sleeps 4
Wailea Ekahi 11C | Snorkeling & Waves Out FrontFrom $330/night · Sleeps 6
From $225/night
Wailea Condo with Private Lanai, Pool & Minutes to Keawakapu Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 10 reviews
Palms at Wailea 1203, offers the perfect location in Wailea. This 2-bedroom/2-bath ground-level unit surrounded by lush landscaping makes this a...
From $1,397/night
Wrap-Around Beach & Ocean Views | Polo Beach 301
Wailea, Hawaii
★★★★★ 10.0/10 · 10 reviews
Welcome to Polo Beach Club 301, a stunning third-floor corner residence that offers breathtaking views of Polo Beach. This spacious unit exemplifies...
From $1,046/night
Polo Beach Club 409 | Ocean View Lanai, Beachfront Pool & Direct Beach Access
Wailea, Hawaii
★★★★★ 10.0/10 · 8 reviews
CORALTREE RESIDENCE COLLECTION presents... Polo Beach Club 409 Experience the laid-back Hawaiian getaway at this spacious 2-bedroom oceanfront condo....
From $1,078/night
Oceanfront Polo Beach 407 - Professionally Managed
Wailea, Hawaii
★★★★★ 10.0/10 · 8 reviews
Polo Beach Club 407 is a premier oceanfront vacation rental located in the upscale resort area of Wailea. This two-bedroom, two-bathroom condo offers...
From $1,541/night
Floor to Ceiling Ocean Views - Wailea Elua 2006
Wailea, Hawaii
★★★★★ 10.0/10 · 8 reviews
Wailea Elua Village 2006 is a charming vacation rental that epitomizes the luxury and tranquility of Maui. This beautifully appointed two-bedroom,...
From $424/night
Recently Renovated - Walk to the Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 7 reviews
Welcome to Wailea Ekahi Village 23C. This residence was fully renovated in the fall of 2024 and features beautiful furnishings and decor to offer you...
From $871/night
Wailea Elua Village 1301 | Front Row to the Ocean, Sunset Views & Steps to Ulua
Wailea, Hawaii
★★★★★ 10.0/10 · 7 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1301 Elua Village sits adjacent to Ulua Beach and connects directly to the 3.2-mile...
From $1,169/night
Elevated Beachfront Views - Wailea Elua 1704
Wailea, Hawaii
★★★★★ 10.0/10 · 7 reviews
Wailea Elua 1704 is a stunning oceanfront vacation rental located a short stroll from one of the top snorkeling beaches on Maui. This spacious...
From $2,107/night
Penthouse Retreat Walk to Wailea Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 7 reviews
Curated with our guests in mind, Wailea Beach Villas PH111\'s outdoor elements are just as immaculate as the home’s interiors. Unwind and enjoy...
From $2,880/night
3BD Wailea Villa - Great for Families | Wailea Beach Villas PH309
Wailea, Hawaii
★★★★★ 10.0/10 · 7 reviews
Penthouse 309 at Wailea Beach Villas offers a distinctive blend of luxury and cultural charm, making it an ideal vacation rental for families or...
From $216/night
Watch the Golfers Play Through
Wailea, Hawaii
★★★★★ 10.0/10 · 6 reviews
Wailea Grand Champions 97 is a premier vacation rental located in the serene tourist retreat of Wailea. This exquisite property combines elegant...
From $291/night
Wailea Ekahi Village 12C - 1 Bedroom Ocea View Condo
Wailea, Hawaii
★★★★★ 10.0/10 · 6 reviews
Wailea Ekahi 12C is a beautiful vacation rental nestled within the landscaped 32 acres that make up Wailea Ekahi Village. This upgraded condo offers...
From $394/night
Recent Renovation - Close to Golf & Dining
Wailea, Hawaii
★★★★★ 10.0/10 · 6 reviews
Do your Maui vacation right! Wailea Grand Champions 95 is surrounded by tropical landscaping and rolling green fairways, that serve as a constant...
From $1,069/night
Beachfront Condo with Postcard Views - Makena Surf F306
Wailea, Hawaii
★★★★★ 10.0/10 · 6 reviews
Experience effortless mingling and entertaining in Makena Surf F306, where the open living area seamlessly connects to a spacious lanai. Enjoy the...
From $1,585/night
Wailea Elua Village 1703 | Oceanfront, Step-Free Walkout, 1 Min to Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 6 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1703Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $1,667/night
Conde Nast Award Winning Property - Wailea Beach Villas E202
Wailea, Hawaii
★★★★★ 10.0/10 · 6 reviews
Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointed interior blends seamlessly...
From $329/night
Stunning ocean view! 2/2 in the heart of Wailea
Wailea, Hawaii
★★★★★ 10.0/10 · 5 reviews
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and...
From $511/night
Ocean Views | Tropical Decor | Professionally Managed
Wailea, Hawaii
★★★★★ 10.0/10 · 5 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1107 Perched above Wailea, 1107 is the most walkable condo in our portfolio — 1,316...
From $552/night
Newly Remodeled-Quiet Location-Ac-Well Equipped-Meticulous Cleaning
Wailea, Hawaii
★★★★★ 10.0/10 · 5 reviews
Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that was just completely remodeled with all new furnishings. This condo is...
From $776/night
Wailea Elua Village 910 | Remodeled, Vaulted Ceilings, 2 Min to Ulua Beach and P
Wailea, Hawaii
★★★★★ 10.0/10 · 5 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 910Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $1,077/night
Recently Renovated - Steps from Snorkeling
Wailea, Hawaii
★★★★★ 10.0/10 · 5 reviews
Wailea Elua 2104 is a charming two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. Designed with an island-inspired...
From $1,182/night
Beachfront Condo – Hear the Waves Crash | Makena Surf C207
Wailea, Hawaii
★★★★★ 10.0/10 · 5 reviews
Welcome to Makena Surf C207, a vacation rental nestled in paradise. This spacious suite offers a serene escape, featuring two large lanais surrounded...
From $2,117/night
Recently Renovated & Professionally Managed Ocean View Villa
Wailea, Hawaii
★★★★★ 10.0/10 · 5 reviews
Welcome to Villa G302, your luxurious Hawaiian escape where relaxation meets elegance. This stunning ocean view villa features two walls of...
From $2,489/night
Recently Renovated | Wrap-Around Ocean Views | Wailea Beach Villas D302
Wailea, Hawaii
★★★★★ 10.0/10 · 5 reviews
Wailea Beach Villas D302 is a stunning, newly renovated ocean-view retreat offering over 2,900 square feet of refined indoor-outdoor living in one of...
From $237/night
Golfer's Dream | Condo on Wailea Course
Wailea, Hawaii
★★★★★ 10.0/10 · 4 reviews
Wailea Grand Champions 31 is a recently updated vacation rental that offers a perfect blend of comfort, style, and convenience in the heart of...
From $523/night
Wailea Ekahi Village 29D | Ocean Views, Resort Pools & Walkable Location
Wailea, Hawaii
★★★★★ 10.0/10 · 4 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 29D From the private lanai, ocean and pool views stretch out before you — Keawakapu...
From $686/night
Prime Location | Snorkeling | Wailea Beach Path
Wailea, Hawaii
★★★★★ 10.0/10 · 4 reviews
Wailea Elua 1203 is a stunning one-bedroom, one-bathroom oceanfront vacation rental located on the ground floor of the prestigious Wailea Elua...
From $897/night
Wailea Ocean Views | Great for Families
Wailea, Hawaii
★★★★★ 10.0/10 · 4 reviews
Wailea Ekahi Village 19B is a two-story, two-bedroom, two-and-a-half-bath townhome that comfortably accommodates up to four guests. This beautifully...
From $2,061/night
Bright & Colorful Ocean View Villa | Wailea Beach Villas PH402
Wailea, Hawaii
★★★★★ 10.0/10 · 4 reviews
Experience the very best in tropical island living from ocean view Wailea Beach Villas Penthouse 402. Revel in sweet sunsets and seasonal whale...
From $3,541/night
Oceanfront 3BR villa w/ private lanai and Wailea Beach access
Wailea, Hawaii
★★★★★ 10.0/10 · 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 $220/night
Wailea Grand Champions 111 | Tennis Views, Resort Pools & Walk to Wailea Shops
Wailea, Hawaii
★★★★★ 10.0/10 · 3 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 111Wailea Grand Champions is an 11-acre country club-style resort set along the...
From $246/night
Ocean Views | Close to Wailea Golf & Beaches
Wailea, Hawaii
★★★★★ 10.0/10 · 3 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1007A spacious 1,316 sq.ft. 2-bedroom condo offering ground-floor convenience and...
From $330/night
Wailea Ekahi 11C | Snorkeling & Waves Out Front
Wailea, Hawaii
★★★★★ 10.0/10 · 3 reviews
Wailea Ekahi 11C is an ideal Hawaiian retreat for friends or families traveling together. Each of the two bedrooms in this spacious condo feature a...