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.
Wailea Ekahi 52B | Resort Level Amenities!
With 34 acres of landscaped resort bordering one of Hawaii’s best beaches, Wailea Ekahi 52B is the ideal place to experience the very best of Hawaii. It’s affordable luxury that’s perfect for two couples wanting to share an island getaway. There’s a minimum stay...
Wailea Ekahi Village 7A - 1 Bedroom Garden View Condo
In a quiet corner, close to the ocean and resort’s pool pavilion, Wailea Ekahi Village 7A offers a place to relax and unwind. Stretch your legs in the morning with a stroll on the cool, green grass just off the lanai and surround yourself with colorful blooms and...
Wailea Elua Village 1502 - 2 Bedroom Ocean View Condo
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...
Makena Surf F304 Beachfront Resort - 2 Bedroom Oceanfront Condo
Makena Surf F304 is a stunning oceanfront vacation rental located in the beautiful Makena region of Maui, Hawaii. This luxurious third-floor condo offers breathtaking views of the Pacific Ocean and is perfect for families or couples seeking a relaxing getaway. The...
Lovely First Floor Townhome! A/C + W/D! Ekahi 25B
Welcome to Tutu’s House! Step into 25B and be transported back to the days as a child visiting your favorite Auntie or Tutu’s (grandma) home. Furnishings are new versions of classic Hawaiiana with bamboo chairs and bar stools and even a fun Queen Size Wall Bed that...
Wailea Ekahi Village 18C - 1 Bedroom Garden View Condo
E Komo Mai. Welcome to Wailea Ekahi Village 18C, a delightful one-bedroom vacation rental located in the stunning Wailea area of Maui! This cozy retreat offers a serene garden view, making it an ideal choice for those seeking a peaceful and relaxing getaway. Upon...
Wailea Ekolu Village 1404 - 1 Bedroom Ocean View Condo
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 Grand Champions 177 - 1 Bedroom Golf Course View Condo
Welcome to Maui\'s Wailea Grand Champions, a paradise nestled in the heart of Wailea. This exquisite one-bedroom, two-bathroom vacation rental offers the perfect blend of comfort, luxury, and breathtaking views, ideal for couples or small families seeking an...
Wailea Elua Village 104 - 1 Bedroom Ocean View Condo
Wailea Elua Village 104 is a stunning Wailea condominium rental that offers a truly unparalleled Hawaii vacation experience. Situated along the pristine golden sands of Ulua Beach on Maui\'s southern shore, this luxurious one-bedroom, two-bathroom condo provides guests...
Wailea Grand Champions 185 - 2 Bedroom Garden View Condo
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...
Wailea Grand Champions 52 - 2 Bedroom Garden View Condo
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...
Wailea Elua Village 1202 - 1 Bedroom Ocean View Condo
Wailea Elua 1202 is a stunning vacation rental property that offers visitors a truly luxurious and unforgettable experience in the heart of Maui\'s renowned Wailea resort area. Situated just steps away from the pristine white sands and crystal-clear waters of Ulua...
REDECORATED! NEW OFFERING SUMMER 2025 - THE PALM COAST F202 OCEAN VIEW GRAND LUXE VILLA SLEEPS 8!
New Offering! Reservations are accepted now. An extensive redecoration is coming soon and F202 will be ready to greet guests as of October 2025.The Palm Coast F202 at Wailea Beach Villas recently joined Private Paradise Villas, and it will be fully refreshed with mostly...
Wailea Point | 2301 - 2 Bedroom Ocean View Condo - 30+ Night Luxury Stays
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 Ekahi Village 12B - Studio Ocean View Condo
Wailea Ekahi Village 12B is a beautiful vacation rental that underwent a complete update in March 2021. Interior designers may want to take notes! This gorgeous ocean view studio is ideal for couples looking for a cozy retreat or solo travelers looking for the perfect...
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...
Wailea Beach Villas G101 - 3 Bedroom Garden View Villa
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...
Wailea Elua Village 1504 - 2 Bedroom Ocean View Condo
Wailea Elua Village 1504 is a luxurious vacation rental located in the picturesque Wailea area of Maui. This beautifully designed two-bedroom, two-bathroom condo will check all the boxes your are looking for in your Maui vacation rental steps from the beach. The...
Wailea Elua Village 1509 - 2 Bedroom Garden View Condo
Wailea Elua Village offers tropical vacation condos set amid Wailea’s resort hotels, making it a perfect luxury destination. Enjoy easy access from this vacation condo at Wailea Elua Village to the restaurants and spas of the Wailea resorts via the picturesque...
Wailea Beach Villas PH104 - 2 Bedroom Garden View Penthouse
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...
Wailea Elua Village 1510 - 2 Bedroom Ocean View Condo
Wailea Elua 1510 is a charming two-bedroom, two-bathroom vacation rental located in the premier Maui vacation destination of Wailea. This upstairs condo offers stunning ocean views and is just a short stroll away from the pristine Ulua Beach, one of the favorite...
Wailea Ekahi Village 42D - 1 Bedroom Garden View Condo
"Welcome to your serene oasis at Wailea Ekahi Village 42D, a meticulously designed 1-bedroom garden view condo that promises an unforgettable stay. This charming retreat features a king-sized bed in the bedroom, ensuring a restful night's sleep, and a cozy living room...
Wailea Beach Villas PH106 - 2 Bedroom Garden View Penthouse
Welcome to Wailea Beach Villas Penthouse 106, a luxurious ground-floor retreat in one of Maui’s 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...
Wailea Ekahi Village 26D - 1 Bedroom Garden View Condo
Escape to paradise in this beautifully appointed one-bedroom vacation rental nestled in the lush tropical gardens of Wailea Ekahi Village. Located on Maui’s sunny south shore, 26D is a tranquil second-floor unit that offers the perfect blend of privacy, comfort,...
Wailea Beach Villas PH107 - 2 Bedroom Garden View Penthouse
Wailea Beach Villas Penthouse 107 is a luxurious haven that embodies the essence of island living, offering breathtaking pool views and peekaboo ocean views from its prime Wailea location. This expansive 2-bedroom villa includes a versatile den that can be used as a...
Wailea Beach Villas PH205 - 3 Bedroom Garden View Penthouse
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...
Makena Surf A204 Beachfront Resort - 2 Bedroom Oceanfront Condo
Makena Surf A204 is a luxurious oceanfront residence offering a serene Hawaiian retreat. This spacious 1,600 square foot condo, located on the second floor, boasts breathtaking ocean views and direct access to the pristine Po\'olenalena Beach. The open-concept layout...
Wailea Elua Village 2102 - 1 Bedroom Garden View Condo
Wailea Elua 2102 is a delightful one-bedroom with a bonus room, two bathroom second-floor condo that comfortably accommodates up to five guests. Designed with a relaxed, island-inspired style, this residence blends casual elegance with modern comfort, creating an...
Makena Surf B204 Beachfront Resort - 2 Bedroom Oceanfront Condo
Experience the ultimate beachfront getaway at this luxurious 2-bedroom oceanfront vacation rental at Makena Surf, located on the stunning shores of Maui. This exquisite condominium offers breathtaking views of the Pacific Ocean and the nearby islands, including Molokini...
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...
Wailea Elua Village 2108 - 2 Bedroom Ocean View Condo
Welcome to Wailea Elua Village #2108. This two-bedroom, two-bath residence is fully remodeled and redecorated, features an extra-large floor plan of more than 1,500 square feet, and boasts gorgeous, elevated views of the ocean, off-shore islets, and lush tropical...
Wailea Elua Village 2402 - 1 Bedroom Ocean View Condo
Wailea Elua Village 2402 is an exquisite ocean-view second-floor condo located in the prestigious Wailea area of Maui. This elevated condo with vaulted ceilings enjoys great views out over the South Maui coastline, especially remarkable during whale season, since you...
Wailea Ekahi Village 47B - 1 Bedroom Garden View Condo
Welcome to your tropical retreat at Wailea Ekahi Village 47B—an 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...
Wailea Ekahi Village 47D - 1 Bedroom Ocean View Condo
Wailea Ekahi 47D is a spacious and beautifully updated one-bedroom, two-bath condo located in one of Wailea’s most sought-after beachfront communities. Perched on a gentle slope, this upper-level unit offers breathtaking ocean views from the private lanai,...
Wailea Ekahi Village 47E - 1 Bedroom Garden View Condo
Wailea Ekahi 47E is a beautiful vacation rental nestled within the landscaped 32 acres of lush tropical gardens that make up Wailea Ekahi Village. This condo offers a perfect blend of comfort and tropical elegance, making it the perfect home to relax and unwind after a...
Wailea Ekahi Village 49B - 1 Bedroom Ocean View Condo
Wailea Ekahi 49B is a stunning ocean view condominium located in the heart of the renowned Wailea resort area. Nestled along the pristine white sand beaches of Keawakapu Beach, this luxurious condo complex offers sits on 34 acres of lush tropical landscaping. Spanning...
Wailea Ekahi Village 49C - 1 Bedroom Ocean View Condo
Wailea Ekahi Village 49C is a charming vacation rental located in one of the most popular Wailea vacation rental communities. This one-bedroom ocean-view condo offers a perfect blend of comfort, luxury, and tropical ambiance, making it an ideal destination for travelers...
Makena Surf F111 Beachfront Resort - 2 Bedroom Oceanfront Condo
Welcome to Makena Surf F111, a stunning ground floor oceanfront vacation condo that embodies the essence of tropical island relaxation. This spacious 1,510 sq. ft. suite features a quaint entryway that leads you into a beautifully furnished living space, complete with...
Wailea Ekahi Village 50C - 1 Bedroom Garden View Condo
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...
Wailea Ekahi Village 51D - Wailea Ekahi Village 51D
Wailea Ekahi Village tropical vacation condos are situated above Maui\'s beautiful Keawakapu Beach and close to all the top Wailea resort hotels. Enjoy easy access from your vacation condo at Wailea Ekahi Village to the restaurants and spas of the Grand Wailea, Four...
Wailea Beach Villas PH403 - 3 Bedroom Ocean View Penthouse
Wailea Beach Villas Penthouse 403 offers a luxurious escape with stunning ocean views and ample space for the whole family. Spanning 2,000 square feet, this penthouse features three bedrooms and three full bathrooms, making it an ideal holiday retreat. Guests can enjoy...
Chic Coastal Living in the Heart of Wailea
This is a NEW listing and it's gorgeous! We are confident you will have a great experience. Welcome to Palms at Wailea 2206 | Your Perfect Hawaiian EscapeStep inside and be instantly captivated by breathtaking views that draw you out to the spacious private lanai....
Wailea Ekahi Village 52D - 1 Bedroom Garden View Condo
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...
Wailea Elua Village 706 - 2 Bedroom Ocean View Condo
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...
Wailea Beach Villas PH404 - 2 Bedroom Ocean View Penthouse
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...
Wailea Ekahi Village 54B - 1 Bedroom Garden View Condo
Wailea Ekahi 54B is a luxurious one-bedroom two-bathroom vacation rental offering an exceptional blend of comfort and elegance, set within the stunning Wailea Ekahi Village. This inviting ground floor condo boasts a prime location with direct access to lush, tropical...
Wailea Elua Village 707 - 2 Bedroom Ocean View Condo
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...
Wailea Ekahi Village 6F - 1 Bedroom Garden View Condo
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...
Wailea Ekolu Village 1203 - 1 Bedroom Ocean View Condo
Wailea Ekolu Village condo #1203 is an exquisite one-bedroom, two-bathroom ocean view retreat designed for discerning travelers seeking the best of Wailea. This sanctuary offers a seamless indoor-outdoor living experience, allowing guests to enjoy breathtaking panoramic...
Wailea Beach Villas PH508 - 3 Bedroom Ocean View Penthouse
Experience Wailea at its absolute best in Penthouse 508, a spectacular 2,893-square-foot residence that stands apart with a totally unique layout—perched at the top of the Wailea Beach Villas with sweeping ocean views, soaring ceilings, and a spacious design...