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 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...
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...
Ocean and fairway views in this spacious, top-floor, 3-BR Grand Champion Villa!
Experience gorgeous ocean and fairway views from this spacious top floor, tastefully decorated, family-friendly, three-bedroom unit. This beautiful condo boasts the largest floor plan available at Grand Champion Villas. Enjoy the views of the islands of Lanai and West...
Premier Ocean Front with Incredible Views! Polo Beach 604
Relax on the lanai and enjoy sweeping views of Molokini and Kahoolawe Island at sunrise or sunset. Stroll along the world famous Wailea Beach Path, enjoy fantastic snorkeling at uncrowded Polo Beach or unwind and sunbathe at the oceanfront pool and jacuzzi.Spend a dream...
*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...
Ho'olei Villas | Wailea Kapili
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...
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....
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...
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
Limited-Time Offer: Stay 5 Nights, Get the 6th Night FreeBook a stay between October 09 and October 18 and enjoy the 6th night free - perfect for extending your getaway at no extra cost!Discover Hawaiian paradise at this beautifully decorated 1 bedroom, 2 bath premium...
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...
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...
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...
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 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...
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...
Grand Champions 108 | Sunset Views + Amenities
Grand Champions 108 stands as a beacon of refined luxury in Wailea, Maui. This meticulously remodeled one-bedroom, two-bathroom villa offers an unparalleled retreat, blending contemporary elegance with island charm. Perched atop an elevated lanai, the villa presents...
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...
Private Lanai with Ocean Views! Updated Furnishings! Polo Beach 203
Relax on the lanai and enjoy sweeping views of Molokini and Kahoolawe Island at sunrise or sunset. Stroll along the world-famous Wailea Beach Path, enjoy fantastic snorkeling at uncrowded Polo Beach, or unwind and sunbathe at the oceanfront pool and jacuzzi.Spend a...
Walk to white sandy beaches - Palms 501
This beautiful, tropical two-bedroom/two-bath condo is just a short 5-minute walk from the world-famous Keawakapu Beach!! Enjoy dreamy sunset strolls along the golden sands or start your day with a peaceful jog through paths lined with lush tropical flowers. Dive into...
Island Luxury at Wailea Elua #302: Expansive Ocean Views and Gorgeous Interior
Wailea Elua #302 – Top-Floor Ocean View Elegance with Artistic Hawaiian TouchesWelcome to Wailea Elua #302, a stunning 1-bedroom, 2-bathroom top-floor end unit located at one of the highest vantage points in the community. This beautifully updated condo features...
Prime Wailea: Split AC, Wailea Ekahi 36E
Wailea Ekahi 36E offers the perfect Hawaiian retreat! You will enjoy this second level condo surrounded by tropical foliage. The private lanai offers a relaxing space with floor to ceiling sliding glass doors, indoor/outdoor living is seamless. Wailea Ekahi no longer...
Top Floor Remodel! Ocean & Fairway Views Ekolu 908
Beautiful and completely remodeled! The moment you walk through the front door, you will be mesmerized by the views and the beautiful upgrades! This top floor unit features a gourmet kitchen with granite counter tops, stainless steel appliances, custom made cabinets and...
Wailea Ekolu 1403 -1 Bed/2 Bath Vacation Condo
6th night free! discounts applied when booked. offer good until Dec 15th, 2025.Fresh new upgrades - new king bed, new wood flooring, new TVs, kitchen appliances, window blinds, lighting, and two comfortable lanais with an outdoor lawn area. New refrigerator, stove,...
April Special: Beautiful, Palms At Wailea Condo #608- 2BR/2BA,Great Location!
The Aloha Spirit is Alive and Well in Maui! It's absolutely beautiful. The best beaches , clean air, amazing sunsets, rainbows, humpback whales and wonderful hiking, along with the best restaurants. The people are the best! Lahaina is gone but memories will always be...
Luxury 2-bedroom with ocean & fairway views, upgraded and beautifully decorated
Luxury awaits you in this beautifully upgraded 2-bedroom condo. Magnificent ocean and fairway views from this beachy unit with 1,056 square ft of living area and bonus lanai space. This is truly a beautifully remodeled and decorated unit!Once you enter this condo, you...
Polo Beach Club 305, you will be drawn to the breathtaking views from lanai.
Polo Beach 305, with Spectacular Ocean Front Views! Located in the highly sought after beachfront stack. Take in an unforgettable sunset or views of Kaho'olawe, Molokini, and The West Maui Mountains!As you enter Polo Beach Club 305, you will be drawn to the breathtaking...
Wailea Grand Champion Golf Villa 2 Bdr/2 Bath
6th night free! discounts applied when booked. offer good until Dec 15th 2025.Comfortable and spacious 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Golf Villas. A fully stocked kitchen for home-cooked meals and a private lanai for outdoor...