Makena Surf G203 | Secluded Ocean Views, Lush Gardens & Poolside RelaxationFrom $1,145/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
Makena Surf G203 | Secluded Ocean Views, Lush Gardens & Poolside RelaxationFrom $1,145/night · Sleeps 6
Top Floor Remodel! Ocean & Fairway Views Ekolu 908From $516/night · Sleeps 5
Prime Wailea: Split AC, Wailea Ekahi 36EFrom $338/night · Sleeps 4
Wailea Grand Champion Golf Villa 2 Bdr/2 BathFrom $395/night · Sleeps 6
Wailea Ekolu 1403 -1 Bed/2 Bath Vacation CondoFrom $244/night · Sleeps 4
April Special: Beautiful, Palms At Wailea Condo #608- 2BR/2BA,Great Location!From $428/night · Sleeps 5
Luxury 2-bedroom with ocean & fairway views, upgraded and beautifully decoratedFrom $460/night · Sleeps 6
Walk to Waves, Snorkeling, Hot TubFrom $1,200/night · Sleeps 6
Wailea Ekolu Village 912 – Ocean-View Couple’s Retreat, Walk to Wailea VillageFrom $440/night · Sleeps 2
Conde Nast Award Winning Property - Wailea Beach Villas PH504From $1,234/night · Sleeps 6
Summer Deal Wailea Condo with Ocean Golf Views Pool and Hot TubFrom $129/night · Sleeps 4
Redesigned 1BD/2BA condo with Haleakala views, near Wailea's beaches + diningFrom $131/night · Sleeps 4
Summer Deal Wailea 2BR Condo with Lanai Pools and Beach AccessFrom $187/night · Sleeps 4
KBM Resorts | FREE CAR | Wailea Elua | 2-Bedroom Condo Condo with Luxury Amenities! WEV-2009From $1,303/night · Sleeps 6
Wailea Ike by AvantStay | Walk to the Beach | Balcony w/ ViewsFrom $305/night · Sleeps 6
Wailea Elua Village 1303 - 2 Bedroom Oceanfront CondoFrom $1,899/night · Sleeps 4
Wailea Ekahi 11A | Four Pools | Resort AmenitiesFrom $269/night · Sleeps 4
Wailea Ekahi Village 12A | Ocean Views, Split-Level, Resort Pools & Beach AccessFrom $512/night · Sleeps 4
Wailea Elua Village 1103 – Oceanview XL Lanai, 1-min to Ulua Beach, Resort PerksFrom $848/night · Sleeps 6
Wailea Ekahi Village 3B | Garden-View Studio Near Pool & BeachFrom $236/night · Sleeps 2
Platinum Rated & Golf Course ViewsFrom $238/night · Sleeps 6
Ekahi 4C - 4 Pools | Beach Access | Professional ManagedFrom $306/night · Sleeps 2
Walk to the Beach, Shops, Pool | Wailea Elua 2008From $853/night · Sleeps 4
Summer Deal Wailea Condo with Golf and Ocean Views Resort PoolsFrom $142/night · Sleeps 4
Summer Deal Wailea Condo with Golf Course Views Pool and Hot TubFrom $198/night · Sleeps 2
Lush Wailea Ground Floor Condo Tropical Oasis Four Pools Keawakapu BeachFrom $333/night · Sleeps 4
Wailea Ekahi Village 9A – 4 Resort Pools, Pickleball, at Keawakapu BeachFrom $527/night · Sleeps 4
Wailea Ekolu Village 1703 – Ocean-View Walkout by the Golf, Walk to Wailea VillaFrom $198/night · Sleeps 4
Garden Studio Steps From The Beach - Wailea Ekahi 4BFrom $303/night · Sleeps 2
Serene Wailea Escape with Island Views & Resort PoolFrom $349/night · Sleeps 6
Wailea Ekahi 48C ~ 1 Bedroom 2 Bath Wailea Condo!From $340/night · Sleeps 4
Amazing! Beautifully Remodeled and Upgraded! Palms at Wailea 403From $372/night · Sleeps 6
Grand Champions 144 | Tropical Golf Resort w/ PoolFrom $254/night · Sleeps 6
From $1,145/night
Makena Surf G203 | Secluded Ocean Views, Lush Gardens & Poolside Relaxation
Wailea, Hawaii
★★★★★ 9.4/10 · 3 reviews
CORALTREE RESIDENCE COLLECTION presents... Makena Surf G203! Immerse yourself in tranquility at this secluded 2-bedroom, second-floor sanctuary...
From $516/night
Top Floor Remodel! Ocean & Fairway Views Ekolu 908
Wailea, Hawaii
★★★★★ 9.2/10 · 72 reviews
Beautiful and completely remodeled! The moment you walk through the front door, you will be mesmerized by the views and the beautiful upgrades! This...
From $338/night
Prime Wailea: Split AC, Wailea Ekahi 36E
Wailea, Hawaii
★★★★★ 9.2/10 · 60 reviews
*Wailea Ekahi 36E | Tropical Retreat Near Keawakapu Beach*Escape to Wailea Ekahi 36E, a beautifully appointed one-bedroom, two-bath condo nestled...
From $395/night
Wailea Grand Champion Golf Villa 2 Bdr/2 Bath
Wailea, Hawaii
★★★★★ 9.2/10 · 43 reviews
New, new, new. Upgrades galore. Fresh paint, new tile, new furniture, flooring, electronics, beds, and more!Professional photos pending! Comfortable...
From $244/night
Wailea Ekolu 1403 -1 Bed/2 Bath Vacation Condo
Wailea, Hawaii
★★★★★ 9.2/10 · 35 reviews
Fresh new upgrades - new king bed, new wood flooring, new TVs, kitchen appliances, window blinds, lighting, and two comfortable lanais with an...
From $428/night
April Special: Beautiful, Palms At Wailea Condo #608- 2BR/2BA,Great Location!
Wailea, Hawaii
★★★★★ 9.2/10 · 35 reviews
The Aloha Spirit is Alive and Well in Maui! It's absolutely beautiful. The best beaches , clean air, amazing sunsets, rainbows, humpback whales and...
From $460/night
Luxury 2-bedroom with ocean & fairway views, upgraded and beautifully decorated
Wailea, Hawaii
★★★★★ 9.2/10 · 17 reviews
Luxury awaits you in this beautifully upgraded 2-bedroom condo. Magnificent ocean and fairway views from this beachy unit with 1,056 square ft of...
From $1,200/night
Walk to Waves, Snorkeling, Hot Tub
Wailea, Hawaii
★★★★★ 9.2/10 · 17 reviews
Welcome to Makena Surf E105, your ideal oceanfront getaway nestled within the luxurious Makena Surf resort, located on the pristine Po\'olenalena...
From $440/night
Wailea Ekolu Village 912 – Ocean-View Couple’s Retreat, Walk to Wailea Village
Wailea, Hawaii
★★★★★ 9.2/10 · 5 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 912An exquisite 1,000 sq.ft. 1-bedroom condo offering elevated hillside views over...
From $1,234/night
Conde Nast Award Winning Property - Wailea Beach Villas PH504
Wailea, Hawaii
★★★★★ 9.2/10 · 5 reviews
Wailea Beach Villas Penthouse 504 enjoys 180 degree views of the Pacific Ocean, Kaho‘olawe, Molokini crater, and Lanai. This generous two-bedroom,...
From $129/night
Summer Deal Wailea Condo with Ocean Golf Views Pool and Hot Tub
Wailea, Hawaii
★★★★★ 9.0/10 · 56 reviews
Views! Views! Views! Experience breathtaking ocean and fairway vistas from this top-floor unit. This spacious condo features a generously sized...
From $131/night
Redesigned 1BD/2BA condo with Haleakala views, near Wailea's beaches + dining
Wailea, Hawaii
★★★★★ 9.0/10 · 47 reviews
Grand Champions 136 is situated in a lush tropical setting. This 1 bedroom / 2 bathroom is located on the top floor with wonderful views of...
From $187/night
Summer Deal Wailea 2BR Condo with Lanai Pools and Beach Access
Wailea, Hawaii
★★★★★ 9.0/10 · 35 reviews
Incredible Renovation! Kick back and relax on your own private lanai and take in wonderful garden views, with some ocean and mountain views. Feel the...
From $1,303/night
KBM Resorts | FREE CAR | Wailea Elua | 2-Bedroom Condo Condo with Luxury Amenities! WEV-2009
Wailea, Hawaii
★★★★★ 9.0/10 · 10 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 $305/night
Wailea Ike by AvantStay | Walk to the Beach | Balcony w/ Views
Wailea, Hawaii
★★★★★ 9.0/10 · 9 reviews
Pack your swimwear and prepare for an unforgettable getaway at this newly renovated condo, where every morning greets you with stunning balcony views...
From $1,899/night
Wailea Elua Village 1303 - 2 Bedroom Oceanfront Condo
Wailea, Hawaii
★★★★★ 9.0/10 · 9 reviews
When vacationing in Wailea Elua 1303, you’ll feel pampered by the extra touches that await you in this suite featuring modern comforts throughout....
From $269/night
Wailea Ekahi 11A | Four Pools | Resort Amenities
Wailea, Hawaii
★★★★★ 9.0/10 · 4 reviews
Wailea Ekahi 11A offers a truly exceptional and luxurious island getaway on Maui. Situated in the prestigious Wailea resort community, this spacious...
From $512/night
Wailea Ekahi Village 12A | Ocean Views, Split-Level, Resort Pools & Beach Access
Wailea, Hawaii
★★★★★ 9.0/10 · 4 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 12AStep off the ground-floor walk-out patio and you're on the tropical grounds —...
From $848/night
Wailea Elua Village 1103 – Oceanview XL Lanai, 1-min to Ulua Beach, Resort Perks
Wailea, Hawaii
★★★★★ 9.0/10 · 4 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1103Elua Village sits steps from Ulua Beach and connects directly to the 3.2-mile...
From $236/night
Wailea Ekahi Village 3B | Garden-View Studio Near Pool & Beach
Wailea, Hawaii
★★★★★ 9.0/10 · 2 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 3BA cozy 600 sq.ft. ground-floor studio, offering step-free access and direct garden...
From $238/night
Platinum Rated & Golf Course Views
Wailea, Hawaii
★★★★★ 9.0/10 · 2 reviews
Nestled in the heart of Wailea, this charming Grand Champions residence offers a tranquil retreat that feels like your own private Hawaiian...
From $306/night
Ekahi 4C - 4 Pools | Beach Access | Professional Managed
Wailea, Hawaii
★★★★★ 9.0/10 · 2 reviews
Wailea Ekahi 3C is a captivating vacation rental that offers a truly idyllic island getaway in the heart of Maui's picturesque Wailea resort area....
From $853/night
Walk to the Beach, Shops, Pool | Wailea Elua 2008
Wailea, Hawaii
★★★★★ 9.0/10 · 2 reviews
Wailea Elua Village 2008 is a luxurious vacation rental situated along the southern coastline of Maui in the desirable Wailea region. This elegant...
From $142/night
Summer Deal Wailea Condo with Golf and Ocean Views Resort Pools
Wailea, Hawaii
★★★★★ 8.8/10 · 46 reviews
Grand Champions 68! Beautiful golf and ocean views.As you enter you will be greeted by the charm of this condo! Open and inviting! Floor to ceiling...
From $198/night
Summer Deal Wailea Condo with Golf Course Views Pool and Hot Tub
Wailea, Hawaii
★★★★★ 8.8/10 · 16 reviews
Perched along the lush fairways of the Wailea Blue Golf Course, Wailea Grand Champions #122 offers the ideal blend of ocean views, tropical serenity,...
From $333/night
Lush Wailea Ground Floor Condo Tropical Oasis Four Pools Keawakapu Beach
Wailea, Hawaii
★★★★★ 8.8/10 · 9 reviews
Enjoy your open and airy living area with breathtaking views of the picturesque foliage through your lanai door in unit 52A! Ample seating available...
From $527/night
Wailea Ekahi Village 9A – 4 Resort Pools, Pickleball, at Keawakapu Beach
Wailea, Hawaii
★★★★★ 8.8/10 · 8 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 9AThis spacious 945 sq.ft. ground-floor condo offers lush tropical garden views and...
From $198/night
Wailea Ekolu Village 1703 – Ocean-View Walkout by the Golf, Walk to Wailea Villa
Wailea, Hawaii
★★★★★ 8.8/10 · 3 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1703An elegant 1,069 sq.ft. 1-bedroom condo offering a spacious hillside retreat with...
From $303/night
Garden Studio Steps From The Beach - Wailea Ekahi 4B
Wailea, Hawaii
★★★★★ 8.8/10 · 3 reviews
Wailea Ekahi 4B is a charming ground-floor vacation studio nestled on a gentle slope in the picturesque Wailea Ekahi Village. This island hideaway...
From $349/night
Serene Wailea Escape with Island Views & Resort Pool
Wailea, Hawaii
★★★★★ 8.6/10 · 79 reviews
The main living area boasts expansive high beam ceilings that add to the wonderful flow of air blowing in off the Shores of Maui. Very spacious and...
From $340/night
Wailea Ekahi 48C ~ 1 Bedroom 2 Bath Wailea Condo!
Wailea, Hawaii
★★★★★ 8.6/10 · 44 reviews
Wailea Ekahi Village - Spacious one bedroom, two bath condo with a enchanting garden view located in the Upper Village. New carpet throughout the...
From $372/night
Amazing! Beautifully Remodeled and Upgraded! Palms at Wailea 403
Wailea, Hawaii
★★★★★ 8.6/10 · 29 reviews
This cool, ground floor condominium is the most spacious 1200 sq ft two-bedroom 'C' plan, with sunken living room, brand new designer furniture, and...
From $254/night
Grand Champions 144 | Tropical Golf Resort w/ Pool
Wailea, Hawaii
★★★★★ 8.6/10 · 16 reviews
Welcome to Grand Champions 144, a spacious three-bedroom, two-bathroom condo that sleeps six guests in beautiful Wailea, Hawaii. This stunning...