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.
Ho\'olei Villas Wailea Kapili - 3 Bedroom Condo Overlooking Pool
This residence has been given the Hawaiian name "Wailea Kapili", which translates to "a Wailea Gathering." It is the perfect accommodation for gathering with friends and family to enjoy the beauty of Maui. This Ho\'olei Residence is a spacious 2,426 square foot three...
*Stroll To The Beach Til Toes In The Sand!*Beautiful Views*Ground Floor*4 Pools*
Wailea Ekahi Village Two bedroom, two-bath, 1505 sq ft. completely remodeled and upgraded, ground floor condo, sleeps six is situated in a low-rise condominium community. The ocean front village is located on Keawakapu Beach in sunny South Maui. The beach has been voted...
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...
Ho'olei Two-Story Townhome with Gourmet Kitchen and Resort Amenities
This property is hotel zoned, and not being affected by the recent proposed legislation.This lovely villa is designed for indoor-outdoor living featuring sliding pocket doors that lead outside to the spacious private lanai. Take advantage of alfresco dining, cool...
Elua Village Contemporary 2bd+2ba Oceanview
New and Fresh! Lots of new features in Wailea Elua Village 2001. We have been busy with major upgrades! New carpet and paint, new beds, new sliding glass lanai doors, new TVs and much more! An elegant kitchen and an expansive lanai are both available for your enjoyment....
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...
Fabulous Ulua Beach & Lush Grounds Await: Wailea Elua 807, Groundfloor Gem!
Wailea Elua #807 – Ground-Floor Serenity with Ocean Breezes and Refined ComfortWelcome to Wailea Elua #807, a beautifully appointed ground-floor, 1-bedroom, 1-bathroom condo designed for peaceful and private escapes in one of Maui’s most exclusive beachfront...
Makena Surf A102 Beachfront Resort - 2 Bedroom Oceanfront Condo
The recently renovated Makena Surf A102 is a prime oceanfront vacation home spanning 1,510 square feet. This ground-floor unit boasts direct beach access from its private lanai, allowing guests to step right onto the sand. The residence features two bedrooms and two...
360 Ocean Views + Full Remodel! Top Floor # 904!
When you think of Hawaii you imagine awe-inspiring views, amazing sunsets and the natural beauty of the wild blue Pacific. These sights are a daily pleasure from the comfort of your own private lanai. This beautiful ocean view home is one of a kind!!Watch the sunset...
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 •...
Ground-Floor Oceanview Home w/Private Lanai, WiFi, Shared Pool + Lots of Privacy
Wailea Ekolu Village 203Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'With a prime location and all the comforts of home, Wailea Ekolu 203 is the perfect setting for your next Maui...
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...
Makena Surf A203 Beachfront Resort - 3 Bedroom Oceanfront Condo
Indulge in luxury at this stunning two-story townhouse, featuring a primary retreat on the second floor complete with a lavish bath and a private ocean view lanai. Enjoy sweeping views of the lush lawn and ocean from every corner, enhanced by decorative art and...
Magnificent ocean views from Polo Beach Club 705, with direct beach access!
Magnificent ocean views from Polo Beach Club 705, with direct beach access! Enjoy the serenity and privacy of one of the best locations in Wailea.As you enter Polo Beach Club 705 you are greeted by the lovely furnishings and decor. You will be drawn to the breathtaking...
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...
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...
Beautifully remodeled with central A/C! Top Floor! Palms at Wailea 206
Fabulous condo! This luxury Palms at Wailea unit is located near the spectacular pool and jacuzzi and all the amenities this popular complex affords.This central air-conditioned 2-bedroom, 2-bath unit is immaculate and beautiful and comes equipped with all the amenities...
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...
Makena Surf B205 Beachfront Resort - 2 Bedroom Oceanfront Condo
Makena Surf B205 is an exquisite oceanfront vacation rental located within the luxurious Makena Surf resort, nestled on the stunning Po\'olenalena Beach in Maui. This beautifully appointed second-floor residence offers a serene escape, perfect for families or couples...
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...
Beautifully Remodeled! Top Floor and Near pool! Palms at Wailea 304
If you are looking for a perfect getaway in paradise, this is it! This luxury Palms at Wailea unit is located near the spectacular pool and Jacuzzi and all the amenities this popular complex affords.This spacious fully air-conditioned two-bedroom two-bath unit is...
1BR, 2BA! Enjoy fairway, & partial ocean views from your private lanai!
Renovated 1 Bedroom 2 Bathroom! Kick back and relax on your own private lanai and take in wonderful garden, fairway, and partial ocean views. Feel the wonderful trade winds and take in the aroma of the beautiful Plumeria trees and Hawaiian foliage. This spacious...
Polo Beach Club 205! Direct ocean front and sunset views!
Polo Beach Club 205! Direct ocean front views! Located in the highly sought-after beachfront stack. Enjoy incredible views of Polo Beach, Molokini Crater, Kaho'olawe, and the West Maui Mountains!As you enter, you will be taken aback by the amazing views from your...
Wailea Luxury on a Budget at Grand Champion Villas - 2 Bd+2 Bath
6th night free! discounts applied when booked. offer good until Dec 15th, 2025.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...
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...
Fantastic Oceanfront unit on ground floor! Spacious and updated Polo Beach 107
Experience true paradise and stunning ocean views from the lanai as you sip on your morning coffee! Stroll along the world famous Wailea Beach Path, enjoy fantastic snorkeling at uncrowded Polo Beach or unwind and sunbathe at the ocean front pool and jacuzzi.This...
Oceanfront 2BR Retreat with Stunning Views and Luxury Amenities Makena Surf B305
Welcome to Makena Surf B305! This unit is all about LOCATION and VIEWS! Makena is located a short five minute drive from all of the restaurants and shops in Wailea but offers the seclusion and privacy from all of the resort traffic! Makena Surf is one of the best kept...
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....
Ocean & Garden Views Await at Wailea Ekahi 34B: Spacious 1BR/2BA Ground Floor
Welcome to Wailea Ekahi 34B where lush tropical foliage surrounds you and views of the majestic Pacific await! This updated 1 bedroom / 2 bathroom unit is the perfect setting for your Maui vacation. This ground floor unit boasts incredible ocean and garden views! Enjoy...
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...
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...
Stunning Ocean Views! Prime Location! Ekolu # 1705
You'll enjoy the terrific location of this comfortable 2 bedroom / 2 bath condo. Ekolu 1705 is walking distance to restaurants and shops and a short drive to the beach. Kick back on multiple lanai options, enjoying the lovely trade winds. Sleep will come easy after a...
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...
Spacious Ground Floor Revitalized Oasis- Discover Wailea Ekahi #22B
Wailea Ekahi #22B – Ground-Floor Elegance with Ocean Breezes and Garden ViewsStep into comfort, space, and tranquility at Wailea Ekahi #22B, a large and light-filled 1-bedroom, 2-bathroom ground-floor retreat just a 2-minute stroll from Keawakapu Beach, the oceanfront...
Wailea Grand Champions Unit 33: Large 2 Br Condo in Wailea Sleeps 6 guests
*New Furniture throughout!! This two-bedroom, two-bath garden-view condo has just been remodeled with all new furniture throughout each room in the condo. The primary bedroom and the guest bedroom both have Cal-King beds plus the living includes a queen sofa sleeper...
Wailea Grand Champions 75 - 2 Bedroom Golf Course & Partial Ocean View
Wailea Grand Champions 75 is an exceptional vacation rental situated in the picturesque Wailea region of Maui. This luxurious property promises an unforgettable escape with its blend of elegance, comfort, and stunning natural beauty. Upon entering Wailea Grand Champions...
Wailea Ekahi Village 15A - 1 Bedroom Garden View Condo
Walk to the beach in minutes from this ground floor condo at Wailea Ekahi Village. Slide open the glass lanai doors of Wailea Ekahi 15A and you will quickly be out on the manicured grass lawns surrounded by palm trees, plumeria trees, and colorful hibsicus. Feel the...
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...
Premium Beachfront Unit with Stunning Views! Polo Beach 405
The location cannot be beat! There is no other accommodation closer to the beach in Wailea! Start your day walking the famed Wailea Beach Path, which begins right out front! Enjoy every sunset on your private and spacious covered lanai with ample seating!Able to...
Fully Air-Conditioned and Near the Pool! Come relax at the Palms at Wailea 303!
The name PALMS AT WAILEA aptly describes the feel of this beautiful complex. Located above the pristine shores of Keawakapu Beach, this impeccably furnished home will provide comfort, luxury, and plenty of room to spread out while you explore and enjoy all that Maui has...
Stunning Views, Walk to Beach! Spacious Ekahi 49F
This listing has views from your lanai will have you coming back year after year--and the beach is a short stroll across the condo property! A cozy one bedroom and one bath second floor, this unit supplies you with everything you need for a memorable vacation. Choose...
Wailea Ekahi 17E | Resort Level Amenities!
The beauty of sand and sparkling waters and the warm Hawaiian sun is calling your name! Wailea Ekahi 17E is a one bedroom, two bathroom condo that sleeps two guests. Take in the ocean view, enjoy the 34 tropical landscaped acres at Wailea Ekahi Village, Keawakapu Beach,...
Wailea Ekahi #8-B Partial Ocean View, Steps to Beach, Easy access to Pool
1 Bedroom Condo, Steps to Keawakapu Beach, 60 steps to Oceanfront Pool.This ground floor one bedroom two bath has a/c throughout. It boasts a large open floor plan where the floor to ceiling sliders in the master bedroom and in the living area all open up onto the...
Wailea Ekahi Village 40C - 1 Bedroom Garden View Condo
Wailea Ekahi Village 40C was fully renovated in the summer of 2021. Open the windows or lanai doors and let the Maui breeze blow through as you relax in this comfortable island suite. You\'ll delight at the explosion of fuchsia bougainvillea blooming all around your...
Grand Champions 108 | Sunset Views + Amenities
Welcome to Grand Champions 108, a beacon of refined luxury in the heart of Wailea, Maui. This beautifully remodeled one-bedroom, two-bath villa blends contemporary elegance with authentic island charm, offering a serene retreat surrounded by lush greenery and ocean...
Ocean Views + Exquisite getaway Wailea Ekahi 53D!
Special Offer: Book 8 or more nights, get 1 night free or Book 12 or more nights, get 2 nights free. Valid on all new reservations booked on or after 10/17/2024.This exquisite, second floor, 1bedroom, bathroom retreat is the perfect Hawaiian getaway. With gorgeous views...
360 Premier Ocean View! Remodeled Ekolu # 1510!
This is a premier unit with panoramic ocean views located just minutes to all Wailea Beaches, The Shops at Wailea and Luxury Hotels! This beautiful condo is fully remodeled with tasteful furnishings, top of the line appliances, exquisite cabinetry, upgraded bathrooms...
Stunning Remodeled Unit with Ocean Views! Ekahi 5E
Welcome to Ekahi 5E! This top floor unit boasts incredible ocean and garden views! It is nestled along a beautiful hillside that embraces the serenity and peacefulness of Maui. Enjoy the views and feel the breeze from the oversized private lanai! Your private lanai...
Makena Surf G203 Beachfront Resort - 2 Bedroom Oceanfront Condo
Makena Surf G203 is a luxurious oceanfront vacation condo located on the second floor of the exclusive Makena Surf resort on Po\'olenalena Beach, Maui. This secluded beachfront property offers the ultimate in tropical island relaxation, providing a peaceful retreat for...
Wailea Ekolu Village 1205 - 2 Bedroom Ocean View Condo
Wailea Ekolu 1205 is a two-bedroom, two-bathroom ocean view vacation residence that comfortably accommodates four people. The sweeping ocean views beyond the Wailea Blue Golf Course and lush tropical landscaping make this private vacation home feel truly idyllic. The...