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.
Tropical Wailea Retreat
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...
Luxurious Wailea Ocean Vistas
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 - Close to Main Pool & Beach! Spacious condo -Sleeps Up to Four
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. NEW EVERYTHING! Complete Remodel! AC and Pool.
If you are looking for a modern, luxurious retreat for families in Wailea with BRAND NEW EVERYTHING, look no further! This unit was completely renovated. Guests can enjoy:— Modern, deluxe kitchen with all new appliances. Fully stocked with everything you need to cook...
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
Welcome to your piece of paradise in a completely remodeled, fully furnished, ground floor unit! Our home is located in Wailea Ekahi, one of the few Kihei and Wailea properties located directly on the beach; no need to cross a road or even sidewalk!Our private corner...
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...
PICTURESQUE OCEAN VIEW CONDO - LAST MINUTE DEAL! BEAUTIFUL WAILEA AT ELUA 2002
Wailea Elua #2002 Ocean View CondoThis newly remodeled in 2021 second floor 2 bedroom and 2 bathroom condo has an open floor plan, large lanai that looks out to the Ocean. Complimentary high-speed internet is included.Elua Village is a premier destination resort, with 2...
4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach
Discover the breathtaking Wailea area in Kihei and indulge in top-notch tropical life at this lavish four-bedroom holiday house. Nestled just minutes away from the pristine Wailea Beach and the vibrant Shops at Wailea, this property offers the perfect blend of...
🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
Wailea Grand Champions Villas -- Condo #188Aloha!You are coming to Maui for your Dream vacation---Why not stay in a Tranquil, spacious condo full of High-end amenities while enjoying the island? We welcome you to share our well-loved Maui paradise in stunning Wailea!...
Luxurious, 2 bedroom / 2 bath, FULL Ocean View Wailea Condo
Situated on 18 acres of perfectly manicured tropical foliage, bordering the award winning Wailea Blue Golf Course, Ekolu Village is an exclusive and desirable complex that is exceptionally quiet and free of any traffic noise. This property is located in less than a 5...
Hoolei Uni 31-2 Ocean view- ideal Wailea location walking to beaches and shops
Dramatic ocean views, this spacious town home is approximately 2500 sq ft of interior footage and 596 sq ft of lanai space. The Hoolei community is located directly across the street from the Four Seasons and the Grand Wailea Resort. Unit 31-2 has the a great location...
Only Steps to Ulua Beach and the main Wailea Ekahi Pool/Pavilion -1 Bd+2Ba
If this vacation home is available, you'll want to reserve it. Wailea Rentals presents: Wailea Ekahi Village 8E - Ekahi means #1 in Hawaiian and that is exactly what Ekahi Village is - 1 of Wailea's top luxury beachfront condominium resorts. Treat yourself to new! New...
Best 2 Bedroom Condo In Wailea - Enjoy Paradise All Year
Aloha and welcome to our home at The Palms at Wailea. The ocean view will take your breath away the minute you step inside. But it's the condo renovation and our commitment to our guests that will keep you coming back.Our remodeled unit has beautiful floors, plenty of...
Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR / 3 BA
Wailea Beach Villas voted as one of the top 100 USA Hotels by the Conde Nast Traveler Readers Choice Awards!Luxury awaits in this exquisite three bedroom, three full baths, 2500 square feet Penthouse Villa J205 with gorgeous ocean view. Our Aloha Kai Suite is elegant...
1BR/2BA Maui Kamaole/Wailea Border. K Cluster @ Tropical Pool!
Personal Touch:We stock everything you need: dish soap, laundry soap, paper towels, napkins, Kleenex, TP, garbage bags, coffee filters etc... All you need to bring is you! We provide the definition of a care free vacation, if this interests you, read on... This is our...
NEWLY REMODELED! Beautiful & Spacious- Two Story Wailea Ocean View 2BR/2.5BA
Aloha! We are back on the rental market after a lengthy remodel! Enjoy beautiful ocean views while relaxing in our very spacious 2 story, 2 bedroom/2.5 bath Condo/Townhouse! Our end unit, #1702, has 1500 sq ft of living area, plus 400 sq ft of lanai/patio area. Great...
Wailea Ekahi 1B Recently Remodeled Ocean View 1st Floor Luxury 1BD 2BA Condo
Unit 1B is located on beautiful Keawakapu Beach in gorgeous Wailea. This totally remodeled lower village, ground floor unit has one large lanai with a beautiful ocean view and Ekahi’s 34 acre tropical landscaped gardens. It has a lanai table that seats 6. It is located...
Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D
Luxurious Tropical Retreat - Unit 31D is truly "one-of-kind"!Ideally located overlooking the lower Ekahi Village, Unit 31D provides our guests with the best of everything Maui has to offer: spectacular views, privacy and a short stroll to the beach and main pool.With...