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.
New Listing- Impressive 3 Bd+2 Bath Vacation Home at Wailea Grand Champions
Bldg. 16 - Unit #153 - A front-row, ground floor, impeccable 3 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is a prime example of what Wailea Grand Champion Golf Villas has to offer in a 3 bdrm + 2 bath category. Upgraded...
Palms at Wailea Villa 806 Ocean View 2BD 2BA
This two-bedroom villa boasts stunning ocean vistas and a tranquil setting within Wailea’s resort community. With a full kitchen, comfortable living space, and balcony overlooking the ocean, it’s ideal for enjoying Maui’s natural beauty. Villa 806 Ocean View 2 Bedroom 2...
New Listing! - Wailea Ekahi 39E - Luxurious Ocean View Condo, Split AC!
Welcome to Wailea Ekahi 39E, a beautifully appointed one-bedroom, two-bath condo offering breathtaking ocean views and the perfect blend of comfort, style, and convenience. Whether you're planning a romantic retreat, a peaceful solo vacation, or a productive remote work...
Sandy Beach Front Property - Family Friendly - 4 min stroll to H2O - Ocean Views
Experience the gold standard of Maui living at Wailea Ekahi 35B. This impeccably remodeled, 5-star oceanfront townhome offers breathtaking views from every floor and a family-friendly, two-story layout. Located in the heart of Wailea in a direct ocean front property,...
Wailea Ekolu 505 ~ Big Ocean Views ~ New Furnishings
Spectacular Ocean and Sunset Views!!A short walk or drive to Wailea’s best beaches.Newly furnished and well appointed home will provide an exceptional experience.Wailea Ekolu is peaceful and spacious development with dinning, coffee, shopping and Maui's best beaches are...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Luxury Oceanview Wailea Point 3-Bed Vacation Home
Discover luxury living at Wailea Point Resort, nestled between prestigious resorts, this oceanfront paradise promises the ultimate South Maui experience. Our 3-bed luxury condo offers four bathrooms, in-suite laundry, two workspaces, and a chef's kitchen with top-tier...
Close to Everything, Stunning Palms at Wailea Condo, Full A/C, Upper Floor
Welcome to Palms at Wailea 2304. Come to Wailea to enjoy the most beautiful beaches and best restaurants Maui has to offer. Get ready to make long-lasting memories while relaxing at this recently updated two-bedroom condo at the beautiful Palms at Wailea. This second...
Summary:Completely remodeled (Sept 2023). Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful...
Wailea Elua 1603: Premier Views, Exquisite Updates!
Wailea Elua Village #1603 boasts some of the best Ocean Views and is located on one of the most prestigious properties on Maui. This condo has been lovingly maintained and updated to ensure it remains a luxury-level choice for those traveling to Maui.Featuring the...
Exquisite Oceanfront Wailea Beach Villas B202
Wailea Beach Villas has been ranked #4 in Hawaii by Condé Nast Readers. This recognition places WBV among the very best resorts in Hawaii, and the best on Maui!This property is hotel zoned, and not being affected by the recent proposed legislation.Be one of the first...
Fully Remodeled Elegance in Wailea 2Bed 2Bath
** PLEASE NOTE: The Pool will be closed from September 15th - September 18th, 2026, for yearly maintenance. Welcome to The Palms at Wailea, where we offer you exceptional experiences in a variety of realms that exceed your expectations. Nestled within the prestigious...
We invite you to come and stay at our spacious suite where you can enjoy the exclusive Wailea lifestyle. Relax & restore in this serene space surrounded by tropical palms!This bright and airy 1 bed/2 bath, corner end unit is a modern Hawaiian retreat. The suite features...
Gem near Keawakapu Beach - Privacy, Ocean Views, Split A/C - Palms at Wailea
The Palms at Wailea #2204 has been totally remodeled. This large condo of 1022 sq feet has soaring ceilings and stunning garden and ocean views from every room. Two covered lanais are ideal for outdoor living and dining. It's only a 7-minute walk to the famous Keawakapu...
Charming Oceanview Oasis: Wailea Elua 802 Surrounded by Lush Tropical Grounds
Wailea Elua #802 – Panoramic Oceanfront Luxury, Fully Remodeled in November 2024Welcome to Wailea Elua #802, a stunning second-floor oceanfront condo that redefines luxury in Maui’s premier resort community. Completely remodeled in November 2024, this 2-bedroom,...
Spring Special! Fantastic Beachfront Wailea Ekahi 2/2
Welcome to my sunny Wailea Ekahi Paradise! This unit is a remodeled, expanded and wonderfully furnished 2 bedroom 2 bathroom ground-floor condo (Unit 43A) is the perfect spot for a family or group vacation! Keawakapu Beach is just a short walk away through beautifully...
Wailea Elua: Huge Ocean Views, Pool, AC & Hot Tub
Summary:Nestled in the scenic beauty of Wailea, this inviting condo promises a delightful escape with everything you need for a memorable stay. Imagine waking up to ocean views, leisurely days by the pool, and evening strolls along the beach. This is a place where you...
Summary:Completely remodeled (Dec 2022). Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful...
Dramatic Ocean Views, Wailea Ekolu 407, Perfect for Couples, Renovated, Split AC
Experience the essence of Maui at Wailea Ekolu 407, a luxurious 1-bedroom, 2-bathroom condo that offers breathtaking panoramic ocean views from the spacious living area, kitchen, primary suite, and oversized lanai. Nestled in the heart of Wailea, this elegant...
Impressive Wailea Ekahi 1 Bd+2Ba Condominium 20G-Adjacent to Keawakapu Beach
Don't miss the best that Wailea Ekahi has to offer. Ekahi 20G - newly remodeled as of August 2025. Full kitchen and bathroom remodel, with all new appliances, Gorgeous! Stay with Wailea Rentals at Wailea Ekahi Village 20G and you and your guests will enjoy premier...
Palms at Wailea 1203 Offers The Perfect Location in Wailea!
Palms at Wailea 1203, offers the perfect location in Wailea. This 2-bedroom/2-bath ground-level unit surrounded by lush landscaping makes this a great Hawaiian retreat!Ideally situated just uphill from gorgeous Keawekapu Beach, The Palms at Wailea is an...
Wailea Ekahi 24C, Paradise in Style! Spacious 2 Bedroom 2 Bathroom, SLEEPS 6.
Welcome to Codge’s Beach House! This 2 bedroom , 2 bathroom unit (SLEEPS 6), was remodeled in late 2022 with ceiling fans, new split ductless AC's, brand new kitchen and bathroom and with a lot of thought for comfort and ease of use. We are on the second floor with 3...
1BEDROOM/2BATH Downstairs Condo in Wailea Ekahi Village #46A -- Locally Owned
Retreat and relax in this comfortable, serene, light and airy, completely remodeled unit. This ground floor unit in the quiet, beachfront Wailea Ekahi Village won't ask you to carry your bags up a single step, while still providing a private and open environment....
Newly Renovated High-end 1 bedroom, 2 bathroom Wailea Condo close to beach
The Palms at Wailea #1804 has been completely renovated, be among the first to enjoy this brand-new high-end renovation in Wailea in which every room has been updated. This bright, spacious condo has a refreshing beach personality, 1000+ sq. ft., and 2 large lanais for...
Luxury Condo in Wailea with sweeping views
2 large master ensuite bedrooms with Cal King beds. Sweeping views of Kaho'olawe, Molokini, and Lanai islands and spectacular sunsets. Beaches, restaurants, and Shops of Wailea all within walking distance. Fully equipped kitchen, with plenty of dining wear and cooking...
Palms at Wailea 1904! Nicely Updated and Great Wailea Location!
Palms at Wailea 1904 is a nicely updated and well-located 2-bedroom, 2-bathroom condo in the beautiful area of Wailea. This condo is the perfect getaway for families or couples traveling together. It features a private lanai with lush garden views, making it a great...
Wailea Oasis: Relax in Your Spacious Villa w/ Lush Tropical Views, Private Lanai
Grand Champions is perfectly situated in Wailea, in spectacular South Maui. World-class beaches, golf, restaurants, and two swimming pools await your visit. Two master suites with king-size beds plus one queen-size sleeper sofa, air conditioning throughout, tastefully...
Stunning 2-bedroom Wailea Elua, walk to beach, ocean view!
Welcome to Wailea Elua #101!A spacious 2-bedroom, 2-bath condo in the heart of Wailea’s resort area. Just a 5-minute walk to Ulua Beach, one of Maui’s best for snorkeling and swimming, this home offers a relaxing tropical retreat with ocean and garden views. Walk to all...
New Listing, Wailea Ekahi 4A, Close to Best Beaches, Shops of Wailea & World Class Golf
Summary:Lovely, Spacious Maui Townhouse: Steps from Keawakapu Beach!The Space:Escape to paradise at Wailea Ekahi Village 4A, Maui's dream vacation rental. This spacious 2-bedroom, 2.5-bathroom townhouse offers the perfect blend of indoor comfort and outdoor...
Wailea Elua 1101 - Beachfront Section - Ocean View -1 Bedroom &NewQualitySofaBed
We are a 1 minute walk from the amazing Ulua Beach. You can see and hear the ocean from our condo. Relax viewing the ocean on a private, quiet lanai surrounded by tropical gardens. Earth-friendly furnishings and complete “green” remodel. Gourmet kitchen, spacious...
Wailea Ekahi 10C - Just steps away from Main Pool & Beach! - Family Managed
Our home is in the 1st (and closest) phase of Ekahi and is just steps away from the main pool pavilion, the beach, and a second pool even closer. Ekahi is a huge complex, so check the complex maps we included before booking. Some units are in another zip code!You have...
130K Hawaiian Reno on Wailea Blue Golf *Ocean View
BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of...
Wailea Beach Villas E-302 on Wailea Beach
Modern living, in one of the best locations at Wailea Beach Villas, with outer island and sunset views that are unmatched. Centrally located in the complex, and only steps away to both pools on property as well as the white sand beach and Wailea Beach path, leading you...
Luxury Wailea Family Condo. Complete Remodel! AC and Pool.
Your Perfect Maui Family Retreat AwaitsExperience the ultimate in modern luxury at this completely renovated condo in Wailea. Just a 10-minute stroll to the pristine shores of Keawakapu Beach and moments from the elegant Shops at Wailea, this impeccably appointed condo...
Grand Champions 105 I Spacious Wailea 3bd
Hawaii Life Vacations proudly presents Grand Champions #105, a beautifully updated 3-bedroom condo located in a serene corner of Grand Champions Villas in Wailea. Nestled against the 8th hole of the Blue Course, this spacious retreat offers stunning mountain views from...
Steps to Kamaole beaches/Upgraded kitchen & baths/2 Pools/Tennis/Close to Wailea
This second floor 2 bedroom/2 bath peek-a-boo ocean view condo is your perfect Maui vacation retreat just across the street from beautiful Kamaole III beach park! Maui Kamaole is one of the lowest density projects in South Kihei and features beautiful landscaping, 2...
Stunning Ocean Front Views, Wailea, Polo Beach Club Condo - unit 303
Welcome to your tropical escape at Polo Beach Club, our cherished slice of paradise! Having fallen in love with this magical location years ago, we are thrilled to be able to share our beautiful condo with you. Nestled at the tranquil south end of Wailea Beach Walk,...
Wailea Elua 803 - Ocean Views, Modern Renovation, Central AC, Wi-Fi, BBQ Grill
Every detail was addressed in the complete and total renovation of this single-level luxury condo at Wailea Elua Village. Upon entering Wailea Elua Village unit 803, you are immediately greeted with panoramic ocean views from the open living area, and the unit is...
Wailea Grand Champion Villas 3-Bedroom updated Home centrally located in Wailea
Aloha, our home is located in the center of Wailea on the first hole of the Wailea Blue Course and is perfect for families or couples. The 3 bedroom home was recently updated, has high ceilings, and large, sliding glass doors that look out over the golf course and...
Luxe Oceanview Hideaway on Wailea Old Blue Golf Course
WAILEA PARADISE HIDEAWAYEscape to a serene and elegant retreat in the heart of Wailea.Set on the renowned Wailea Old Blue Golf Course, this ocean-view villa blends luxury with convenience—just minutes from the beach, the Shops at Wailea, fine dining, and world-class...
Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, Maui
Introducing: Wailea Elua 1308. Offering a front row beachfront location, this immaculately maintained unit features unobstructed ocean view corridors, privacy, convenient access to the Wailea Beach Path, and one of the world’s best beaches as the front yard. Extensively...
Spectacular Panoramic Ocean Views - Private Ohana - Wailea Custom Pole Home
Live like a local at the Ocean Blue Ohana. You'll have the entire private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500...
100KContemporaryHawaiian Reno in Wailea-Beach/Golf
Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa. World Class Golf+Shopping. Ground flr condo with...
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
The best location in Wailea! Quick 2-minute walk to Wailea beach, shops, restaurants & the stunningly scenic Wailea Beach Path. BOOKING CALENDAR/MINIMUM NIGHT STAY:Our calendar opens 1 year in advance. Please reach out if you want to inquire about specific dates prior...
Steps to Beach. Stunning View. Lovely 2BR Condo near Wailea
Enjoy paradise at one of Maui's premier beaches. Our air-conditioned retreat features a clean and bright interior, offering stunning views from the main living area. Enjoy cooking in a well-equipped kitchen and relax with beach chairs, umbrellas, and boogie boards...
Cozy Treasure Nestled on a Lush Oceanfront Property - Wailea Elua 1508
Wailea Elua #1508 – Partial Ocean Views & Comfort Near PoolSet within the prestigious Wailea Elua Village, Wailea Elua #1508 offers an ideal balance of peaceful luxury and island convenience. This spacious 2-bedroom, 2-bathroom condo features partial ocean views, a...
Discount Week Rates! Elua Premier 2-Bedroom Front-Row... Oceanfront Unit!
Ulua Beach Premier 2-Bedroom Oceanfront Unit...Unobstructed Ocean Views!Welcome to Wailea Ulua #1002! This recently renovated luxury beachfront 2 bedroom/2 bath residence is located in the heart of Wailea on Maui Sunny South Shore. Within steps of the unit you are on...
Wailea Ekahi 40A - 5-Star South Maui Oasis
*Please note-The main pool will be closed for refurbishment from August 10, 2026-October 15, 2026. Three other smaller pools will be available for use, but the main pool will be closed during this time*Welcome to your piece of paradise in a completely remodeled, fully...
16B; Ocean View, Quiet Beachfront King Studio in Luxurious Wailea Ekahi Resort
Ocean View, King Bed, quiet Ground floor Studio condo, in the beautiful Wailea Ekahi Resort, near one of the 4 private pools and a short walk to the beach.Enhanced cleaning protocols and private ground floor entrance with Lanai opening onto the beautiful gardens and...
There is NO PLACE like Wailea especially in a two-storey townhouse! Enjoy!
WELCOME TO OUR HAWAIIAN RETREAT in Wailea!We purchased our second property in Wailea - November 2019. Enjoy your getaway at our new home-away from home! We spent the 2019 holiday season buying new furniture for EVERY room, decorating, cleaning and repairing this...