Wailea Elua 1507 in the Wailea ResortFrom $1,395/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 Elua 1507 in the Wailea ResortFrom $1,395/night · Sleeps 4
WE 1605 Wailea Hillside Condo w/ Lanai, AC & Golf Views Near BeachesFrom $414/night · Sleeps 6
New Fall Special Ocean-View Cottage Above Kihei Near Wailea BeachesFrom $202/night · Sleeps 5
*NEW* Fall Sale Wailea Blue Fairway and Sunset-View CondoFrom $214/night · Sleeps 4
New Partial Ocean-View Wailea Ohana Near Beach and ShopsFrom $473/night · Sleeps 4
Wailea Elua #1903: 1 BR, 1.5 BA Condominium in Kihei, Sleeps 2From $1,395/night · Sleeps 2
NEW Palms at Wailea 2 Bedroom Garden-View Villa | Car Incl. w/ 6 nights | PAW-1706 by KBMFrom $314/night · Sleeps 4
Wailea Beach penthouse w/ ocean view and pool accessFrom $1,482/night · Sleeps 6
NEW! KBM Resorts | Ocean Views | FREE CAR | Wailea Ekahi | 1-Bedroom Condo with Luxury Amenities! WKV-45CFrom $221/night · Sleeps 2
Luxurious Wailea Ekahi 19A - Ground Floor with Ocean Views & Easy Beach AccessFrom $704/night · Sleeps 7
Wailea Elua 1104 - Ocean Views, Central A/C, Walk to Ulua Beach, Shops & Dining!From $742/night · Sleeps 6
Wailea Ekolu 804 | 1BD/2BA | Ocean Views | Prime Wailea LocationFrom $143/night · Sleeps 4
The Palms at Wailea 1805 - Luxury 2BR condo, large lanai, Full AC, Kitchen, WiFiFrom $334/night · Sleeps 6
2 2 Luxurious Wailea Oceanview Resort VistasFrom $461/night · Sleeps 6
The Best Condo in Wailea Ekahi VillageFrom $684/night · Sleeps 6
Wailea Elua Unit 806From $1,395/night · Sleeps 6
Wailea Ekahi 49A 1BD Condo in Wailea with Garden Lanai & Beach AccessFrom $208/night · Sleeps 4
Wailea Ekolu 1608 | 1 Bedroom | Prime Wailea Location with Golf Course ViewsFrom $273/night · Sleeps 4
Ocean and Molokini Views by Beach - Wailea Ekahi 13DFrom $276/night · Sleeps 4
Wailea Ekolu 408 Spacious Second-Floor Retreat with Panoramic Ocean ViewsFrom $343/night · Sleeps 4
Wailea Blue Golf Course Condo-Walk to Shops, BeachFrom $431/night · Sleeps 6
Peaceful Golf Course Retreat with Partial Ocean Views-Wailea Grand Champions #78From $179/night · Sleeps 6
NEW! GC 148-Front-Row Sunsets Over the Ocean & Golf Course | Wailea Luxury 2BRFrom $203/night · Sleeps 5
Tranquil Stay at Wailea Ekahi Oceanfront Complex-2 Beds-BalconyFrom $340/night · Sleeps 4
Ground Floor Wailea Condo with Private Lanai Near BeachesFrom $355/night · Sleeps 4
Wailea Ekahi 52D - Wailea 1BR Condo, Garden Lanai, AC, Island Luxury Beach CondoFrom $379/night · Sleeps 4
Wailea Elua | Steps to Ulua Beach, Ocean ViewsFrom $1,644/night · Sleeps 6
Palms at Wailea 406 Spacious Condo, Large Lanai, A/C, Partial Ocean ViewFrom $281/night · Sleeps 4
New Listing | Maui Oasis at The Grand Champions unit 53From $335/night · Sleeps 4
Wailea Grand Champions 185 | Spacious Wailea Condo Near Beaches and GolfFrom $344/night · Sleeps 6
New! Rare 3 BR Wailea Condo-Beaches, Shops & GolfFrom $405/night · Sleeps 8
Wailea Ekahi 42C - Peekaboo Ocean Views, 2 Full Baths, King TempurPedic, Full ACFrom $461/night · Sleeps 4
Oceanview Paradise: Tropical Retreat in WaileaFrom $475/night · Sleeps 8
From $1,395/night
Wailea Elua 1507 in the Wailea Resort
Kihei, Hawaii
★★★★★ 68 reviews
Beautiful finishes and amenities define this restful space. Access to pickleball courts, workout center, two pools and jacuzzi spas on property....
From $414/night
WE 1605 Wailea Hillside Condo w/ Lanai, AC & Golf Views Near Beaches
Kihei, Hawaii
★★★★★ 54 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.Welcome to...
From $202/night
New Fall Special Ocean-View Cottage Above Kihei Near Wailea Beaches
Kihei, Hawaii
★★★★★ 40 reviews
Summary:Let the morning begin on the covered lanai, with ocean views, a little extra quiet, and nowhere you need to be in a hurry. Set in peaceful...
From $214/night
*NEW* Fall Sale Wailea Blue Fairway and Sunset-View Condo
Kihei, Hawaii
★★★★★ 31 reviews
Summary:Settle onto the furnished balcony and watch the sun drop toward the ocean beyond the Wailea Blue fairway. This one-bedroom, two-bath condo...
From $473/night
New Partial Ocean-View Wailea Ohana Near Beach and Shops
Kihei, Hawaii
★★★★★ 23 reviews
Summary:Bring your coffee to the lanai and catch the partial ocean view before the beach day begins. This bright, one-bedroom Wailea condo sleeps...
From $1,395/night
Wailea Elua #1903: 1 BR, 1.5 BA Condominium in Kihei, Sleeps 2
Kihei, Hawaii
★★★★★ 16 reviews
Unparalleled oceanfront views and serene location with a privacy garden and spacious outdoor area for relaxing and having dinner. Beautiful finishes...
From $314/night
NEW Palms at Wailea 2 Bedroom Garden-View Villa | Car Incl. w/ 6 nights | PAW-1706 by KBM
Lahaina, Hawaii
★★★★★ 14 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 $1,482/night
Wailea Beach penthouse w/ ocean view and pool access
Kihei, Hawaii
★★★★★ 7 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 $221/night
NEW! KBM Resorts | Ocean Views | FREE CAR | Wailea Ekahi | 1-Bedroom Condo with Luxury Amenities! WKV-45C
Kihei, Hawaii
★★★★★ 6 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 $704/night
Luxurious Wailea Ekahi 19A - Ground Floor with Ocean Views & Easy Beach Access
Wailea, Maui, Hawaii
★★★★★ 6 reviews
Wailea Ekahi #19A – Spacious Townhouse Comfort Near Keawakapu BeachWelcome to Wailea Ekahi #19A, a rare and spacious 2-bedroom, 3-bathroom townhouse...
From $742/night
Wailea Elua 1104 - Ocean Views, Central A/C, Walk to Ulua Beach, Shops & Dining!
Kihei, Hawaii
★★★★★ 6 reviews
The primary bedroom features a king bed with quality linens and a private bathroom. The guest bedroom is furnished with two twin beds, making the...
From $143/night
Wailea Ekolu 804 | 1BD/2BA | Ocean Views | Prime Wailea Location
Kihei, Hawaii
★★★★★ 3 reviews
Interior photos coming soon. Wailea Ekolu 804 | 1BD/2BA | Ocean Views | Prime Wailea LocationWelcome to Wailea Ekolu 804, a beautifully appointed...
From $334/night
The Palms at Wailea 1805 - Luxury 2BR condo, large lanai, Full AC, Kitchen, WiFi
Kihei, Hawaii
★★★★★ 3 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 $461/night
2 2 Luxurious Wailea Oceanview Resort Vistas
Wailea-Makena, Hawaii
★★★★★ 3 reviews
Summary:Perched overlooking Wailea on southern Maui, this wonderful two-bedroom condo is a dreamy escape into open airy luxury. With incredible ocean...
From $684/night
The Best Condo in Wailea Ekahi Village
Kihei, Hawaii
★★★★★ 3 reviews
WOW! Unit 32-A is the most AMAZING unit in all of Wailea Ekahi! It was designer renovated from floor to ceiling over a six month period with no...
From $1,395/night
Wailea Elua Unit 806
Kihei, Hawaii
★★★★★ 3 reviews
An incredible 1,250 sq ft three bedroom / two bath condo in Wailea's Luxury Resort. It includes access to Wailea Elua Village Resort's pickleball...
From $208/night
Wailea Ekahi 49A 1BD Condo in Wailea with Garden Lanai & Beach Access
Kihei, Hawaii
★★★★★ 2 reviews
Welcome to Your Maui Retreat: This comfortable Wailea condo offers an easygoing South Maui escape set just above Keawakapu Beach, one of the area's...
From $273/night
Wailea Ekolu 1608 | 1 Bedroom | Prime Wailea Location with Golf Course Views
Kihei, Hawaii
★★★★★ 2 reviews
Wailea Ekolu 1608 | 1 Bedroom, 2 Bath | Prime Wailea Location with Golf Course ViewsExperience the beauty and convenience of Wailea from this...
From $276/night
Ocean and Molokini Views by Beach - Wailea Ekahi 13D
Kihei, Hawaii
★★★★★ 2 reviews
Book with us and come to Maui to explore everything we have to offer!Ocean views can be enjoyed from Wailea Ekahi Unit 13D. This one-bedroom features...
From $343/night
Wailea Ekolu 408 Spacious Second-Floor Retreat with Panoramic Ocean Views
Kihei, Hawaii
★★★★★ 2 reviews
Experience an elevated Maui escape at Wailea Ekolu Village Unit 408, where comfort, views, and location come together for a truly memorable stay....
From $431/night
Wailea Blue Golf Course Condo-Walk to Shops, Beach
Kihei, Hawaii
★★★★★ 2 reviews
New! Wailea Blue Golf Course Condo-Walk to Shops, Beach | Luxury Golf & Beach Retreat 2 Bedrooms | 2 Bathrooms | 1,150 Sq Ft | Sleeps 6Experience the...
From $179/night
Peaceful Golf Course Retreat with Partial Ocean Views-Wailea Grand Champions #78
Wailea, Maui, Hawaii
★★★★★ 1 reviews
Beautiful Golf Course Views | Wailea Grand Champions #78Escape to the peaceful beauty of Wailea Grand Champions #78, a spacious two-bedroom,...
From $203/night
NEW! GC 148-Front-Row Sunsets Over the Ocean & Golf Course | Wailea Luxury 2BR
Kihei, Hawaii
★★★★★ 1 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 $340/night
Tranquil Stay at Wailea Ekahi Oceanfront Complex-2 Beds-Balcony
Kihei, Hawaii
★★★★★ 1 reviews
Relax in our renovated 1BR/1BA condo at Wailea Ekahi Village, perfect for up to 4 guests. This bright and comfortable upstairs second-floor condo in...
From $355/night
Ground Floor Wailea Condo with Private Lanai Near Beaches
Kihei, Hawaii
★★★★★ 1 reviews
Welcome to your tropical home away from home in beautiful Wailea. Located within the highly sought-after Palms at Wailea resort community, this...
From $379/night
Wailea Ekahi 52D - Wailea 1BR Condo, Garden Lanai, AC, Island Luxury Beach Condo
Kihei, Hawaii
★★★★★ 1 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 $1,644/night
Wailea Elua | Steps to Ulua Beach, Ocean Views
Wailea-Makena, Hawaii
★★★★★ 1 reviews
Summary:New to our portfolio — not new to hospitality. We're the same 5-star team behind other top-rated Wailea Elua vacation rentals. This freshly...
From $281/night
Palms at Wailea 406 Spacious Condo, Large Lanai, A/C, Partial Ocean View
Kihei, Hawaii
Escape to your private Wailea retreat at The Palms at Wailea, where island comfort, partial ocean views, and tropical serenity create the perfect...
From $335/night
New Listing | Maui Oasis at The Grand Champions unit 53
Kihei, Hawaii
Forget your worries in the spacious and serene space. This recently refreshed bright, 1 bedroom, 2 bath condo is perfect for up to 4 guests to enjoy...
From $344/night
Wailea Grand Champions 185 | Spacious Wailea Condo Near Beaches and Golf
Kihei, Hawaii
Wailea Grand Champions 185 is a beautifully updated 2-bedroom, 2-bath condo in the heart of Wailea, offering a spacious and comfortable retreat for...
From $405/night
New! Rare 3 BR Wailea Condo-Beaches, Shops & Golf
Wailea-Makena, Hawaii
Summary:Panoramic Ocean + Golf Views | 3BR/2BA Luxury Wailea Villa | Walk to Shops & BeachWelcome to your upscale Maui retreat at Wailea Grand...
From $461/night
Wailea Ekahi 42C - Peekaboo Ocean Views, 2 Full Baths, King TempurPedic, Full AC
Kihei, Hawaii
* * * * 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 $475/night
Oceanview Paradise: Tropical Retreat in Wailea
Wailea-Makena, Hawaii
Welcome to our beautiful, elegantly remodeled 2-bedroom, 2-bathroom condo in the prestigious Wailea Grand Champions Villas. Perched on the 2nd floor,...