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.
Incredibly Large Polynesian Style Villa in Wailea
Spend your vacation in this villa like Polynesian style vacation rental located at the beautiful Palms at Wailea Resort on the Maui's prestigious southern coast. The central air conditioned 1,515 Sq Ft spacious two bedroom, two and a half bath unit is the dream Hawaii...
Wailea Ekolu #708
This Wailea Ekolu retreat goes hand in hand with your Maui experience. Here you will find a clean, open, beautiful condominium, with an amazing ocean view from everywhere within the condo. This is an ideal retreat, in a perfect setting that's a fabulous value.Wailea...
Wailea Elua Village 2401 - 1 Bedroom Ocean View Condo
Completely renovated in 2019, Wailea Elua 2401 is a stunning vacation condo that features a large private wrap-around lanai with breathtaking ocean views. This beautifully designed rental offers a serene indoor/outdoor living space, perfect for enjoying Maui\'s...
Wailea Beach Villas PH302 - 2 Bedroom Ocean View Penthouse
Wailea Beach Villas Penthouse 302, with breathtaking views of the pristine Pacific Ocean, awaits. Take joy in the comfort of luxury and tranquility as it seamlessly infuses with lush tropical surroundings creating long lasting memories. Impeccable contemporary finishes...
Wailea Elua Village 208 - 1 Bedroom Ocean View Condo
Welcome to Wailea Elua 208, where paradise meets luxury! This stunning one-bedroom ocean view vacation rental is the perfect getaway for those seeking both tranquility and adventure. Located in the heart of Wailea, this coastal retreat offers breathtaking views of the...
Wailea Elua Village 1607 - 3 Bedroom Oceanfront Condo
Wailea Elua 1607 is a luxurious ground floor oceanfront vacation rental located in the exclusive Wailea Elua Village. This spacious 1,701 square foot condominium features three bedrooms and two bathrooms, making it an ideal retreat for families or groups of friends...
Wailea Beach Villas D301 - 3 Bedroom Ocean View Villa
Discover for yourself why D301 is one of the most requested Villas in our vacation rental collection. Impressive artwork by internationally known Maui artist Elan Vital provides a fabulous backdrop to the welcoming great room in rich jewel colors of amethyst and jade...
Wailea Elua Village 1001 - 2 Bedroom Oceanfront Condo
Wailea Elua Village #1001 is a stunning oceanfront sanctuary that has recently undergone a complete transformation. For discerning travelers who enjoy the best of Wailea, the extended outdoor living space allows you to enjoy panoramic ocean views while relaxing with a...
Wailea Ekahi Village 17B - 1 Bedroom Garden View Condo
Welcome to Wailea Ekahi 17B, a one-bedroom residence in beautiful Wailea! This vacation rental offers a spacious and comfortable living space, perfect for couples or small families looking for a relaxing getaway. Step onto the large lanai with spectacular garden views...
Wailea Ekahi Village 15D - 1 Bedroom Garden View Condo
Welcome to Wailea Ekahi 15D, a stunning one-bedroom, one-bathroom vacation rental nestled in the heart of Wailea. This second floor vacation condo features a covered lanai along the lush greenbelt that terraces between buildings and leads down to the ocean. Partial...
Stunning Golf Course & Garden Views - WAILEA GRAND CHAMPION #142
Wailea Grand Champions #142- Garden View Comfort in the Heart of WaileaWelcome to Wailea Grand Champions #142, a beautifully maintained one-bedroom, two-bathroom villa set among lush tropical gardens and offering a peaceful retreat in one of Maui’s most sought-after...
Wailea Ekolu 403, Prime Location, Stunning Ocean Views, Spacious Lanai, Split AC
Welcome to Wailea Ekolu 403, a stunning Maui vacation rental offering breathtaking ocean views, luxurious comfort, and a prime location in the heart of Wailea. This spacious two-bedroom, two-bathroom condo sits on the lush fairways of the Wailea Blue Golf Course and...
NEW - Wailea Getaway - steps to great pool & beach
Summary:Aloha, if you are looking for the perfect place to call home in Maui, you just found it! Our Wailea Ekahi Villa is a spacious and private home away from home that makes you feel far from it all yet is still close to everything!Situated above what is widely...
Wailea Ekahi 45D - Ocean & Garden Views, Beautifully Renovated, Split AC, Wi-Fi!
Escape to paradise in this luxurious 1-bedroom, 2-bath condo located in the heart of Wailea, Maui. Enjoy breathtaking ocean views and vibrant sunsets from your private lanai, setting the perfect tone for your island getaway. With Keawakapu Beach and Mokapu Beach just a...
Newly remodeled 2-bedroom! Palms at Wailea 2303
Experience paradise in this newly remodeled 2-bedroom, 2-bathroom condo at Palms at Wailea, 2303. Nestled in a private corner of the property, this tropical oasis offers stunning sunset views, lush surroundings, and one of the largest floor plans that Palms at Wailea...
Prime Wailea Location! Wailea Ekahi 37E
Discover Hawaiian paradise at this beautifully decorated 1 bedroom, 2 bath premium condo in the oceanfront Ekahi Village resort. Highlights include: • Spacious primary suite with king bed • Living area with sleeper sofa • Split AC • Fully-equipped kitchen • Dining area...
Gorgeous Remodel! Two King Suites & Huge Ocean Views! Close To Wailea Beaches
Come experience this recently renovated gem located in the highly desired Wailea Ekolu. Expansive panoramic ocean views, natural lighting, gorgeous art, stylish furniture, and a spacious lanai are just a few of the highlights of this beautiful space. This unit has been...
Wailea Ekolu 206 -Gorgeous Ocean View - AC - Close to Wailea Beach!
E Komo Mai to our luxury 2 bedroom unit on the 2nd floor with a beautiful ocean view and a spacious interior. From our comfortable lanai seating you have a full 180 degree view of the islands of Molokini, Kahoolawe, Lanai, and the West Maui Mountains while enjoying your...
Palms at Wailea 1201! Perfect location in Wailea!
Palms at Wailea 1201! Perfect location in Wailea! This 2-bed/2-bath condo offers the perfect getaway for families or couples traveling together. Enjoy lounging or dining al fresco on your private lanai! Complete with seating for six. The floor to ceiling sliding glass...
Palms at Wailea 705 - Beautifully renovated ground floor unit in premium location, Split AC
The Palms at Wailea 705, a 2 bedroom, 2 bath ground level unit, is your perfect Wailea location. Featuring Mediterranean accents and beautifully manicured grounds, you will be welcomed by the open and inviting living space. Complete with large sectional, with queen...
Spectacular Oceanfront Views with Split AC -Wailea
Kihei Surfside #507 features Incredible views from the lanai, kitchen, dining, and living areas. Completely renovated featuring porcelain tile flooring, custom cabinetry, granite countertops, and a fully equipped kitchen with stainless steel appliances. Bath has a...
Renovated Luxury Palms at Wailea 703: Prime Location, Split AC, Close to Pool!
Welcome to Palms at Wailea 703, your luxurious oasis in the heart of Wailea Resort, Maui's premier destination. This ground-floor, fully air-conditioned condo offers nearly 1,200 sq. ft of meticulously upgraded interior space as well as a spacious wrap around lanai....
Tropical garden view Wailea condo
Grand Champions 8 is a 2 bedroom, 2 bathroom condo featuring amenities such as a private lanai, air-conditioning and a washer/dryer. Located on the 3rd floor, this condo can comfortably accommodate up to 6 guests with a King-size bed in the master bedroom, a Queen-size...
Spacious Condo Near Kihei and Wailea Beaches - Kam III and Keawakapu Beach.
Come enjoy this tranquil unit with modern updated furnishings and two great lanais. Unit 59 has 2 bedrooms and 2 bathrooms with plenty of room inside and out. Well stocked with free Wifi and guest amenities. Close to the large swimming pool, hot tub, tennis court,...
Fantastic ALL NEWLY DECORATED Wailea condo
WELCOME to The Palms at Wailea, Unit 202 - your home away from home! This unit has been completely refurbished and newly decorated. The 2nd floor location provides nice vistas and a cool breeze from the large lanai (BR has AC). The living room has a new queen size sofa...
Wailea Luxury on a Budget at Grand Champion Villas - 2 Bd+2 Bath
Bldg. 13 - Unit #118 - wonderful upgrades in a comfortable and spacious 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Golf Villas. Wailea Grand Champions Golf Villas is in the heart of the Wailea Resort Community in sunny South Maui, nestled...
GC 163 Spacious Wailea 2BD w AC Pool Close to Beach
Grand Champions 163 Spacious 2Bedroom, 2Bathroom Luxurious Wailea Condo. Ideal Location to Walk to Beach, Tennis, Golf, Fine Dining, Luxury Shopping, and so much more. FREE daily activities included with your stay value up to $956! Complimentary admission, every day of...
Wailea Ekahi6D NEWLY UPDATED 2nd Floor, Part Ocean View,1 min walk to Beach&Pool
Hale Wailea 6D – Wailea Ekahi Village[TA-164-628-0704-01]Welcome to Hale Wailea 6D, an elegantly updated, spacious second-floor condo nestled within the serene and beautifully landscaped Wailea Ekahi Village. This quiet, newly listed unit offers an exceptional location...
Beautiful - Palms at Wailea 1802
Located in the Kihei/Wailea area, in the world-famous Wailea Resort community, The Palms at Wailea complex boasts a beautiful pool, hot tub and is conveniently located close to the Shops of Wailea, luxury hotels, stylish boutiques, great restaurants, tennis, the Wailea...
Wailea Hm W/ Priv. Tennis/Pickleball Court Steps from Keawakapu Beach
Enjoy Old Hawaii at its best just steps from Keawakapu Beach. A spacious and tastefully decorated home, suitable for entertaining friends in the huge great room (kitchen, living room, formal dining) which open to the huge tiled lanai where you can BBQ and dine. Relax in...
Beautiful Condo, Private Lanai, Near Wailea Beaches
Address for this Condo: Grand Champions, 155 Wailea Ike Pl #5, Kihei HI 96753***Professionally Cleaned Condo, No-contact Check-In/Check Out*** Welcome to your beautiful island getaway at the luxurious Grand Champions Unit #5. This spacious condo has an open great room...
Heart of Wailea, Remodeled Kitchen + AC! Ekahi 45A
Full remodel! New AC, appliances and furnishings! Wailea Ekahi 45A is a 1 bed, 2 bath condo conveniently located on the ground floor. It has exceptional garden views with TWO large private lanais.This unit is fully equipped with all that you will need for a great...
WAILEA BEACH CONDO W/ OCEAN VIEWS!! NEW RATES
NEWLY REMODELED BEACH CHIC CONDO with ocean views, in the heart of Wailea. Our Wailea condo offers 2 bedrooms, and 2½ bathrooms, with over 1500 square feet of indoor living space, and two lanais boasting another 500 square feet of outdoor living space on two levels! The...
Spacious bright and airy! Ground floor! Palms at Wailea 609
Luxury awaits at this beautifully decorated Palms at Wailea condo. With an open and inviting floor plan, there is plenty of room to spread out after a day of enjoying all that Maui has to offer. The private ground floor location makes this the perfect getaway.Maui's...
WAILEA EKAHI VILLAGE 27C -- HUGE 2 FLOOR TOWNHOUSE WITH SPECTACULAR OCEAN VIEWS!
*****UPDATE: New, mini-split air conditioning system installed in August, 2025*****Ekahi Village 27C is a beautifully-decorated, updated and meticulously-maintained one bedroom, one-and-a-half bathroom condo in South Maui's prestigious Wailea resorts. The condo features...
Palms At Wailea 2002- RARE FIND - Multi Level townhouse in Wailea!
This 3 bedroom 3 bath multi level condominium apartment is like a private home! From the entry you can step up to the open living area with a ocean view lanai. The spacious living area can easily accommodate a family get together with the entertainment area and...
Wailea Grand Champions 168 - Complete Remodel - Amazing Golf Course/Ocean Views
Hawaii Tax ID: TA-144-497-4592-01COMPLETELY REMODELED - GOLF COURSE & OCEAN VIEWSGrand Champions #168 is a impeccably kept one-bedroom two-bath luxury villa with amazing golf course and limited ocean views. The unit is located on the 7th fairway of the the Wailea Blue...
Wailea Ekahi 51E, Amazing Ocean Views, Walk to Beach, Sunset View, Large Lanai
View! View! View! Imagine sipping gourmet coffee while enjoying the stunning ocean views and listening to the birds chirping! Imagine waking up to the mesmerizing sight of the ocean from the comfort of your bed! Imagine a sunset dinner on the lanai or taking a nap on...
Wailea Elua Village Fresh and Contemporary 2Bdr+2 Bath Oceanview Condominium
6th night free! discounts applied when booked. offer good until Dec 15th 2025.New, New, New! New paint, carpet, appliances, furniture, TV's, linens, and more to come in 2025! Top Floor Elua Village vacation home with big ocean views from the lanai, living room, and...
The Sweet Spot - Wailea Elua 3-Bdr/3-Bath Beachfront Paradise Townhouse #1004
New, New, New. Major upgrades! New floors, lighting, furniture, beds, appliances, paint, lanai furniture and artwork. Check out the new photos.This is the one, the best location at Elua. Beachfront 3 BD+3 BA private townhouse with a courtyard and a private beach lanai....
Fantastic Wailea Ekahi Beachfront Condo 45F
Welcome to my sunny Wailea Paradise! This refreshed and tastefully decorated second-floor condo (Unit 45F) has fantastic ocean and garden views and is the perfect spot for a romantic getaway or family vacation. Keawakapu Beach is just a short walk away through...
Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectaular View
Polo #406 is a beautiful, comfortable unit overlooking the ocean. It offers breathtaking views of Molokini, West Maui, Kahoolawe, and Lanai. The unobstructed sunsets are absolutely stunning!While staying at the Polo Beach Club, guests are steps away from a private,...
Wailea Ekahi 31B, 1 BR/2BA, Lower Greenbelt, Ocean View
Please read under Rules & policies-Rental Agreement the new COVID-19 Rules & Guidelines- and the Waiver of Liability Agreement that must be signed upon arrival.Welcome to our remodeled and reconfigured ground level 1 bedroom, 2 full bathrooms luxury condominium...
Wailea Ekolu 304 - Luxurious Front-Row Unit with Amazing Ocean & Golf Views
Hawaii Tax ID: TA-144-497-4592-01 FRONT-ROW UNIT - STUNNING OCEAN & GOLF COURSE VIEWSWailea Ekolu #304 is a luxurious condominium situated at the front row of Ekolu on the 15th hole of the Wailea Blue Course with panoramic views of Molokini and Kahoolawe islands. Every...
Wailea Ekahi 33A 1bd/2bth, luxury, remodel, 3 min walk to beach, many amenities
Wailea Ekahi 33A is a beautiful, romantic, family friendly, 1,100 square-foot 1 bedroom, 2 bath condo in a magnificent, lush tropical paradise resort on spectacular Keawakapu beach. Views are of a tropical garden with partial ocean and mountain views. The condo has...
Luxurious 1 BR, 2 BA Wailea- Remodeled Bathrooms.
Our villa is a one bedroom, 2 bathroom on the ground floor with a very large lanai, which features sliding doors that expand the living room into the lanai. This feature expands the already spacious 1022 sq feet into an impressive 1500 sq feet. Hida- couch and single...
Wailea Ekolu 510 - Ocean Views, Private Lanais, Renovated 2-Story with Split AC!
This extra-spacious two-story town-home-styled condo has no common walls and no one above, with a premiere location at Wailea Ekolu unit 510. Enjoy panoramic ocean views from Makena and Molokini to the West Maui Mountains, from the lanai and from the inside of the unit...
Wailea Elua 1401 - Beautiful Ground Floor 1BR Oceanfront Unit on Ulua Beach
Welcome to Wailea Elua Village, a premier gated community nestled in the heart of Wailea. Our ground-floor beachfront condominium (#1401) offers the perfect blend of luxury, privacy, and island living—ideal for two (adults only) seeking a serene getaway.Set within 24...
Beautifully remodeled! Partial Ocean Views! Top Floor! Palms at Wailea 1704
You're sure to have a fabulous stay! This luxury Palms at Wailea unit is located near the spectacular pool and jacuzzi and all the amenities this popular complex affords.This 2 bedroom 2 bath unit is immaculate and beautiful and comes equipped with all the amenities so...
Spacious 2BD/2BA Condo in Wailea Resort Serene Garden and Mountain Views
Fabulous value in Wailea Resort! If you want the perfect and spacious 2-bed/2-bath condo that is tastefully decorated, offers complete privacy and serenity, and features a lanai surrounded by lush shrubbery, this is it! Bright and airy, this unit is located in a quiet,...