Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui
Wailea is Maui's most refined resort area, offering a curated selection of luxury vacation rentals. Choose from spacious oceanview condos, private beachfront villas, or gated residences-each within walking distance to top beaches like Wailea Beach, Polo Beach, and Ulua Beach. With championship golf, fine dining, luxury spas, and The Shops at Wailea nearby, Wailea is perfect for honeymoons, family vacations, and long-term stays.
Browse Wailea Vacation Rentals by condo/hotel name:
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 retreat, 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
- Ho'olei 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 perfect for long stays
- Consistently sunny weather and calm swimming beaches
Plan Your Stay in Wailea
Wailea offers the best of South Maui-tranquil surroundings, world-class amenities, and stunning natural beauty. Whether you're visiting for a romantic retreat or a long-term tropical escape, Wailea vacation rentals provide the perfect home base for a luxurious island experience.
Spectacular Views at Wailea Elua 2010: Tranquil Oasis on Lush Oceanfront Grounds
Wailea Elua #2010 – Elevated Island Comfort with Panoramic ViewsEnjoy the perfect blend of comfort and convenience at Wailea Elua #2010, a beautifully maintained 2-bedroom, 2-bathroom partial ocean view condo. Located on the second floor, this spacious unit offers...
Amazing Gem Nestled on Lush & Beachfront Grounds -Wailea Elua 2106
Wailea Elua #2106 – Elevated Island Comfort with Ocean & Village ViewsWelcome to Wailea Elua #2106, a beautifully updated second-floor condo offering tranquil garden surroundings and ocean views in one of Wailea’s most sought-after beachfront communities. With spacious...
Snorkel Directly Out Front - Wailea Elua 1502
Situated near the center of the resort, Wailea Elua 1502 is siutated near the putting green and central swimming pool. Just a short walk away is the oceanside Wailea Beach Walk where you can stroll along the shore for a few miles on a paved path and watch Hawaiian sea...
Ground-Level Beauty on a Verdant Oceanfront Property - Wailea Elua 1601
Wailea Elua #1601 – Oceanfront Luxury with Upgraded Interior & Ground Floor AccessStep into effortless island living at Wailea Elua #1601, a beautifully upgraded 1-bedroom, 2-bathroom oceanfront condo designed for relaxation, comfort, and style. With a convenient...
Minutes from Wailea Beaches, Dining & Golf
Wailea Ekolu 1404 is a beautifully appointed one-bedroom, two-bathroom vacation rental that offers an idyllic escape in Maui\'s popular town of Wailea. This elevated condo on the second floor boasts stunning ocean views and a serene ambiance. Upon entering, guests eyes...
Wailea Ekolu 408 Spacious Second-Floor Retreat with Panoramic Ocean Views
Experience the perfect Maui getaway at Wailea Ekolu 408, a charming 1-bedroom, 2-bath condominium situated on the second floor. This inviting vacation retreat feels spacious and airy, featuring vaulted ceilings and sweeping ocean views that stretch from West Maui to...
Maui Wailea 3 Bedroom Luxurious Home
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Wailea is waiting for you at this perfect 3 bedroom house. This warm, single-level home spans over 3,100 square feet, featuring 3 bedrooms and 2.5 baths, thoughtfully designed to blend...
Ocean and Molokini Views by Beach - Wailea Ekahi 13D
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 a California-king bed, and queen sofa bed in the living room. With vaulted ceilings and a bright, open floor plan, this...
Ocean View w/AC - Wailea Elua 306
Book with us and come to Maui to explore everything we have to offer!Wailea Elua is a premier resort located on Ulua Beach in the heart of Wailea. Maui's sunny south shore has some of the best beaches on the island. Ulua Beach is a top snorkeling and dive location in...
Wailea Ekahi 49A 1BD Condo in Wailea with Garden Lanai & Beach Access
Wailea Ekahi 49A Enjoy Your Next Maui Vacation from this 1Bedroom, 2 Bathroom Wailea Condo. Amazing Convenient Location Just a Short Stroll from the BeachWelcome to Your Maui Retreat: This comfortable Wailea condo offers an easygoing South Maui escape set just above...
2 2 Luxurious Wailea Oceanview Resort Vistas
Summary:Perched overlooking Wailea on southern Maui, this wonderful two-bedroom condo is a dreamy escape into open airy luxury. With incredible ocean views, and every amenity a Maui visitor could hope for, guests will fall in love with Wailea's beautiful lushness, while...
Wailea Beach Villas | Penthouse Panoramic Ocean Views | KBM Resorts | 2 Units, 6 Bedrooms | ML-3485
** 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 and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Wailea Beach Villas K207 Luxury 2-Bed Penthouse with Partial Ocean Views
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 best on Maui!This property is hotel zoned, and not affected by the recent proposed legislation.Welcome to your luxurious...
Experience luxury in Wailea Ekolu 1106, a spacious 2BR Stunning Ocean views
Wailea Ekolu 1106 Breathtaking Panoramic Ocean and Neighboring Island Views from High Above Wailea MauiWelcome to your Maui Retreat: Wailea Ekolu 1106 is a newly remodeled 2-bedroom, 2-bath upper-level townhome tucked into the serene Wailea Ekolu Village on South Maui's...
** 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 and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Incredibly roomy, adjacent to the best beaches/Wailea
Extremely roomy, high-end 1-bedroom 2-bathroom, deluxe 1039 square feet condo at the gateway to Wailea. Remodled and features a king bed, high-end furnishings, and a sofa bed. The property has two pools, two hot tubs, two tennis courts and lush gardens. Home boasts...
WE 1605 Wailea Hillside Condo w/ Lanai, AC & Golf Views Near Beaches
Wailea Ekolu 1605 Experience Wailea Maui from this Hillside Retreat on the Golf Course, Minutes from Beaches, Dining and ShoppingWelcome to your Maui Retreat: A beautifully updated 2-bedroom, 2-bath condo nestled in the lush tropical slopes of Wailea. From the inviting...
Ocean View Bliss on Wailea Beach Path
Wailea Point is the ultimate in privacy and elegance for those seeking stays of 30 nights or longer. For shorter stays, please select from one of our other beautiful Wailea resort properties. The finest development in the finest neighborhood on the finest Hawaiian...
Wailea Perfection - Professionally Managed
Welcome to your dream vacation in Wailea, Maui! This beautiful two-bedroom residence combines comfort, style, and convenience for an unforgettable stay in paradise. Upon entering, you\'ll be welcomed by a spacious, open living area, tastefully furnished for a relaxed...
Guest Favorite at Wailea Grand Champions
This two-bedroom, two-bath villa at Wailea Grand Champions offers a perfect blend of contemporary style and tropical paradise. The open floor plan seamlessly connects the fully-equipped kitchen, dining area, and spacious living room, creating an inviting atmosphere for...
Recently Renovated - Wailea Golf Views
Welcome to Wailea Grand Champions 102, a luxurious 2-bedroom, 2-bathroom residence nestled between the fairways of one of Maui\'s most popular championship golf courses. This spacious second-floor unit, spanning over 1,400 square feet, offers a perfect blend of privacy...
Wailea Beach Villas PH508 | Pools | Hot Tubs
Experience Wailea at its absolute best in Penthouse 508, a spectacular 2,893-square-foot residence that stands apart with a totally unique layoutâperched at the top of the Wailea Beach Villas with sweeping ocean views, soaring ceilings, and a spacious design unlike...
Unforgettable Views - Ocean Sunsets - Wailea Elua 707
Ideally situated in a quiet corner along the northern edge of the resort, Wailea Elua Village 707 is just a short stroll to the beachfront pavilion with swimming pool. This vacation rental in the heart of Wailea offers guests a comfortable and upgraded home which...
Modern Ocean View Elegance - Wailea Beach Villas PH404
Wailea Beach Villas Penthouse 404 is a stunning two-bedroom plus den, two-bathroom ocean view residence offering over 1,978 sq. ft. of elegant indoor-outdoor living. Situated on the fourth floor, this penthouse enjoys sweeping views of the Pacific Ocean, Kaho\'olawe and...
Newly Renovated - Professionally Managed | Wailea Elua 706
Welcome to your dream vacation retreat in Wailea! As you step inside the newly renovated Wailea Elua 706, you\'ll immediately be captivated by the spacious and thoughtfully designed interior. The open concept living area is flooded with natural light, creating a warm...
Stunning Wailea Villa with Resort Amenities
Welcome to Wailea Beach Villas Penthouse 205, an elegant retreat that showcases sophisticated furnishings, vibrant colors, and striking artwork. This family-friendly penthouse features three bedrooms and three full baths, offering ample space for families or groups to...
Recently Renovated - Wailea Beach Villas Excellence
Welcome to Wailea Beach Villas Penthouse 106, a luxurious ground-floor retreat in one of Mauiâs most prestigious beachfront communities. This stunning 1,899-square-foot villa offers the perfect blend of island elegance and modern comfort, making it an exceptional...
Award-Winning Resort & Amenities | Wailea Beach Villas PH104
Marvel at the sophisticated style and décor of Wailea Beach Villas Penthouse 104, where a touch of Bali influence seamlessly merges with rustic undertones to create an unforgettable ambiance. The interior design captivates with elements like a textured wall-mounted...
Private Plunge Pool + Lanai Lounge | Wailea Beach Villas G101
Villa G101 is, simply stated, lovely. Swaying palms and a smiling Buddha welcome you into the golden pearl and shell inlay foyer of this beautiful three bedroom, three and a half bath luxury vacation home. 3,592 square feet provide you indoor-outdoor living in the...
Complete Renovation - Everything Brand New | Wailea Ekahi 6F
Wailea Ekahi Village 6F is a premier vacation rental located in the heart of Wailea, Maui. This one-bedroom, two-bathroom condo located within the resort community of the Wailea Ekahi Village, a low-density collection of condo clusters set across 34 acres of beautifully...
Bright & Colorful Beach Condo at Wailea Ekahi
Wailea Ekahi 52 is a luxurious vacation rental property located in the heart of the idyllic Wailea resort community on the southern shores of Maui. This spacious, one-bedroom, one-bathroom condominium offers guests a serene and indulgent island getaway, with all the...
Walk to Favorite Beach - Wailea Ekahi 50C
Experience the ultimate in island luxury with a stay at Wailea Ekahi 50C, a beautiful one-bedroom, one-bathroom vacation rental situated in the heart of Wailea. This elegant ground floor condo offers the perfect blend of modern comfort and tropical charm. From the...
Indoor-Outdoor Tropical Living - Wailea Ekahi 47B
Welcome to your tropical retreat at Wailea Ekahi Village 47Bâan ideal vacation escape for families or a group of friends. This beautifully appointed ground-floor residence offers the perfect blend of comfort, space, and convenience. With serene garden views and easy...
Chic Coastal Living in the Heart of Wailea
** PLEASE NOTE: The Pool will be closed from September 15th - September 18th, 2026, for yearly maintenance. A brand-new split air-conditioning system has been installed throughout the property, ensuring year-round comfort with contemporary efficiency and quiet...
** 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 and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Wailea Ekolu 1608 | 1 Bedroom | Prime Wailea Location with Golf Course Views
Experience the beauty and convenience of Wailea from this tastefully appointed 1-bedroom, 2-bath condo at Wailea Ekolu 1608. Perfectly situated along the fairway of Wailea’s prestigious Blue Golf Course, this ground-level home offers comfort, privacy, and stunning...
Wailea Ekolu 804 | 1BD/2BA | Ocean Views | Prime Wailea Location
Interior photos coming soon. Wailea Ekolu 804 | 1BD/2BA | Ocean Views | Prime Wailea LocationWelcome to Wailea Ekolu 804, a beautifully appointed one-bedroom, two-bathroom retreat perfectly positioned in the heart of Wailea. This spacious condo is nestled along the...
** 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 and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Refined Resort Wailea Oceanview Vistas
Summary:Perched overlooking Wailea on southern Maui, this wonderful two-bedroom condo is a dreamy escape into open airy luxury. With incredible ocean views, and every amenity a Maui visitor could hope for, guests will fall in love with Wailea's beautiful lushness, while...
WAILEA POINT Sweet 2 Bedroom/3 Bath Oceanview Condominium
Please call or email us about the dates for your visit. Free Car promotion! Want a mini-Cooper or similar ride while you're here on Maui - Ask us! New media posted! Check out the new photos and video. Make yourself home at Wailea Point Village 3003. A first-floor...
Tranquil Stay at Wailea Ekahi Oceanfront Complex-2 Beds-Balcony
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 Building 36 features a California King bed, a Queen Murphy bed, a fully stocked kitchen, and modern amenities including...
Cozy 1-bedroom condo with AC, WiFi in lovely Wailea-Makena
This enchanting condo in Wailea-Makena is the perfect home base for your trip. With 1 bedroom featuring a cozy king bed and a stylish living room with a sofa bed, this awesome property is ideal for couples or small families. Open floor plan living area which opens to a...
Wailea Ekahi 6E-Gorgeous Condo, #1 Location, Serene/Private, steps to Pool/Beach
***Please note: This unit is under NEW ownership. The previous owner had a 10/10 rating with 67 reviews!LOCATION, LOCATION, LOCATION is everything at Ekahi Village! Ekahi Village is a premiere condo complex in beautiful Wailea, Maui. Unit 6E is perfectly situated within...
Oceanview Paradise: Tropical Retreat in Wailea
Welcome to our beautiful, elegantly remodeled 2-bedroom, 2-bathroom condo in the prestigious Wailea Grand Champions Villas. Perched on the 2nd floor, this luxurious condo offers breathtaking ocean views and a spacious, open floor plan with tasteful modern finishes.Upon...
Impressive Wailea Point 2 Bedroom+Loft/2 Bath Oceanview Condominium
Yes, you can rent a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment. Each of our privately...
Wailea Point 3 Bedroom/3+ Bath Oceanview Condominium #2503
Yes, you can enjoy a holiday and vacation stay at Wailea Point, the iconic red roofs on Maui's wonderful southern shore; and at a rate lower than a suite at the Wailea hotels. 2503 just may be the 'best location in the whole property'; with an expansive outdoor lanai...
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment....
Palms at Wailea Villa 1210 Garden Deluxe 1 BD 2 BA
This charming one-bedroom garden-view villa is located in Maui’s sought-after Wailea resort community. With a full kitchen, open concept living area, and private patio, it’s a perfect base for enjoying nearby beaches, world-class golf, and island dining. Villa 1210...
Large Charming Ocean View studio in terrific Wailea with WiFi, AC
Comfort meets convenience. Our spacious bedroom suite features two queen beds, a covered lanai overlooking gorgeous tropical scenery and stunning ocean sunsets. Nearby tennis/pickleball courts, and golf, active leisure is just steps away. AC wall unit and ceiling fan...
Luxurious Wailea Ekahi 19A - Ground Floor with Ocean Views & Easy Beach Access
Wailea Ekahi #19A – Spacious Townhouse Comfort Near Keawakapu BeachWelcome to Wailea Ekahi #19A, a rare and spacious 2-bedroom, 2-bathroom townhouse nestled within the beautifully landscaped Wailea Ekahi Village. Located just steps from world-famous Keawakapu Beach and...