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 #24-3-BEAUTIFULLY APPOINTED VILLA-SLEEPS 10-METICULOUS CLEANING
Book With Confidence This Luxurious 3 Bedroom, 3.5 Bathroom (2619 sq. ft) Villa That Provides Everything That You Need To Have A Great Vacation. The House Offers Tremendous Vacation Experience With It's Amenities, Location, And Level Of Finishes. It Is Managed By PMI...
Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC
Welcome to Wailea Ekolu 310, experience breathtaking, panoramic ocean views from main living area and over-sized lanai of this spacious single level luxury condo, in the heart of Wailea and convenient to world class golf, tennis, restaurants and shopping. Sweeping and...
EXQUISITE REMODEL-SLEEPS 8-WELL EQUIPPED-AC-METICULOUS CLEANING
Book with confidence, this stunning, 2 bedroom, 2 bathroom spacious condo that has been completely remodeled from top to bottom. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the...
Wailea Beach Villas | PH112
Awaken to the sweet sounds of palm trees swaying in the tropical breeze from Wailea Beach Villas PH112. Spanning 2,500 square feet, this main level, corner villa fuses a Hawaiian vibe with warm, earthy interior tones. The wraparound lanai offers peekaboo views of the...
Wailea Beach Villas | B101
You will feel like a rock star in this oceanfront villa with its owner’s gold and platinum records displayed alongside a baby grand piano. Villa B101 sits oceanfront within a secluded garden area surrounding a private plunge pool. A short stroll leads you to the...
Tranquil Oceanfront Escape! Central AC! Polo 402!
Book 5 nights and enjoy the 6th night free! Valid for all new reservations arriving after 1/15/2025.This updated condo in a gorgeous oceanfront property is a tranquil escape from the everyday. Nestled in a quiet area, this home away from home offers unparalleled access...
Great view-close to beach!Fully remodeled!Sleeps 5!Bldg 30 Remaining Spring $225
This is a beautiful vacation condominium in the prestigious Wailea resort area regarded as the 'sunny side' of Maui! The Ekahi complex has just completed the construction of our brand new Pavilion at the beach and it is fabulous!! It has a lovely ocean view and an...
BEAUTIFUL BRAND NEW REMODEL-OCEAN VIEWS-SLEEPS 8-AC-WELL EQUIPPED
Book with confidence, this stunning, 2 bedroom, 2 bathroom spacious condo that has been newly remodeled. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available 24/7...
Largest Two Bedroom/ Two Bath in the Village, Sleeps Eight & Close to the Beach
Located in the lower village, ground floor unit #20C has two lanais and a patio. The condo is surrounded by a private, tropical lawn area where children may securely play. The very light and airy 1700 square foot unit is situated on the corner of the building and...
Polo Beach 106! Steps from the Beach! Amazing Views! Favorite Location!
Welcome to your own private oasis! This stunning oceanfront condo is just steps away from the beach, offering breathtaking views of the ocean and the sound of waves crashing on the shore.Visitors have been returning to Polo Beach Club for generations, and #106 will be...
Enjoy comfort in Wailea, a spacious 2BD/2BA condo with garden views
Grand Champions 130. Beautifully decorated with an island feel you will have a true sense of home away from home. This spacious 2 Bedroom, 2 Bathroom unit is conveniently located on the top floor and centrally located in the heart of Wailea!This comfortable 2bd/2bath...
Outstanding Wailea 3 bed/2 ba Grand Champion #94 - big lanai and ocean views
Bldg. 10 - Unit #94 - New, New New. New roof, new carpet, new appliances, new bed - renewed throughout, an impeccable 3 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is the finest that Wailea Grand Champion Golf Villas has to offer...
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 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...
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...
Renovated 2BR/2BA Wailea Ekahi 26A: Ground-Floor Condo with Ocean & Sunset Views
Welcome to Wailea Ekahi Village 26A, two bedroom/two bathroom ground-floor condominium unit that has been completely renovated and offers a clean, contemporary feel. As you enter this luxury living space, premium wood tone flooring stretches throughout the spacious...
Wailea Elua Village | 208
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...
*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....
Wailea Elua Village | 1607
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...
Makena Surf | A203 | Beachfront Resort
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...
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
Wailea Ekahi 37ELimited-Time Offer • Stay 5 Nights, Get the 6th Night FreeBook a stay for August and all of September (offer not valid for booking dates August 29 through September 1) and enjoy the 6th night free—perfect for extending your getaway at no extra...
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...
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
Bldg. 13 - Unit #118 -New carpet, furniture, air conditioners and electronics, 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...
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...
Unbeatable Ocean-View Condo in Palms at Wailea
Discover the pinnacle of luxury island living in Wailea Maui, where this newly remodeled 2-bedroom, 2-bathroom condo in the prestigious Palms of Wailea complex awaits discerning guests. Unit 1406 is not just a place to stay; it's an upscale experience meticulously...
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...
Wailea Ekahi Village | 17B
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...
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...
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...
Makena Surf | B205 | Beachfront Resort
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...