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 Beach Villas PH207 - 2 Bedroom Garden View Penthouse
Upon entering your Wailea Beach Villas PH207, you'll be captivated by the open floor plan, which seamlessly integrates a cozy living room, a quiet den with shoji screen doors, a gourmet kitchen, and a dining area. Sliding doors lead to a lanai equipped with a built-in...
Wailea Elua 3 Bedroom+2 Bath Spacious Beach Home with Oceanview Lanai
This is the one! If it's available, you'll want to reserve it. A real Maui home-away-from-home. New carpet in bedrooms, new bedroom furniture, lots of additional new personal touches! If you are looking for an impressive vacation home with new Ohia wood cabinets,...
Wailea Beach Villas PH209 - 3 Bedroom Garden View Penthouse
Welcome to Wailea Beach Villas Penthouse 209, a beautifully furnished 2,600 sq. ft. garden view suite that offers a serene escape overlooking the family pool. This open and airy vacation rental is designed for relaxation and leisure, featuring an expansive tiled great...
Wailea Elua Village 2012 - 1 Bedroom Ocean View Condo
Wailea Elua Village 2012 is a luxurious vacation rental located in the stunning Wailea area of Maui. This one-bedroom, two-bathroom condo offers an ideal retreat for couples or small families, providing a perfect blend of comfort and elegance. The property is part of a...
Wailea Ekahi 54A: Completely Remodeled & Panoramic Ocean View
Our Family has Two - Two Bedroom/Two Bathroom Units above and Below Each other in Ekahi Village. This is great for Families or large groups traveling together. Both units tend to be among the most popular in the entire complex! VIEWS: Ocean views from nearly every...
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...
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 Ekahi Village 3C - 1 Bedroom Garden View Condo
Wailea Ekahi 3C is a captivating vacation rental that offers a truly idyllic island getaway in the heart of Maui\'s picturesque Wailea resort area. Nestled within the lush, meticulously-maintained 34 acre Ekahi Village complex, this spacious one-bedroom, one-bathroom...
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...
Stunning ocean view! 2/2 in the heart of Wailea
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning...
PERFECT Maui Getaway! Wailea Ekolu Luxury Ocean View Top Floor Condo
Welcome to ocean view luxury in the heart of Wailea; welcome to your perfect Maui getaway. This 2 bedroom, 2 bathroom renovated condo in the Wailea Ekolu neighborhood gives you all the amenities of home, combined with all the luxury of a resort, and all within a 15...
Wailea Beach Villas PH210 - 2 Bedroom Garden View Penthouse
Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms designed with tropical island elegance. This vacation rental welcomes families with its spacious layout, offering stylish...
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...
Wailea Ekahi Village 3E - 1 Bedroom Garden View Condo
Wailea Ekahi 3E is a charming one-bedroom vacation rental located in the picturesque Wailea Ekahi Village. Situated on the second floor, this condo offers elevated views over the tropical grounds lush with colorful island landscaping. The vaulted ceilings and oversized...
Wailea Elua Resort Gorgeous Remodel #1507
Wonderful ocean views and serene location with a privacy garden and spacious outdoor area for relaxing, using the grill and having dinner. Beautiful finishes and amenities throughout this restful space. Access to tennis courts, putting green, workout center, pools and...
Wailea Elua Village 2104 - 2 Bedroom Garden View Condo
Wailea Elua 2104 is a charming two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. Designed with an island-inspired aesthetic, this condo blends comfort with contemporary style, making it an ideal getaway for families or groups of friends....
New Listing, Wailea Ekahi 4A, Close to Best Beaches, Shops of Wailea & World Class Golf
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 living.Unwind in Style:Indulge in expansive living areas, ideal for families or...
Ultimate Oceanfront Luxury - Polo Beach Club #706 in Wailea, Maui
Polo Beach Club 706 is an ideal home base for your tropical getaway. Make your Maui experience one to be remembered. Whether you’re celebrating with family, vacationing with friends, or simply seeking a peaceful and private alternative to a high-end hotel, our...
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...
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...
Wailea Ekahi Village 42C - 1 Bedroom Garden View Condo
This 1,090 square foot one-bedroom, two bathroom vacation rental sleeps four comfortably. Wailea Ekahi Village 42C is conveniently located close to the pool, but offers a quiet sanctuary surrounded by lush greenery. Featuring contemporary, yet comfortable décor...
Wailea Beach Villas PH306 - 2 Bedroom Ocean View Penthouse
Settle into your very own slice of Maui paradise with a stay in Wailea Beach Villas PH306. This exquisite two bedroom, two bathroom penthouse with exceptional ocean and island views are sure to inspire the luxury, comfort and serenity you deserve. Thoughtfully designed...
Wailea Beach Villas PH307 - 2 Bedroom Ocean View Penthouse
In Wailea Beach Villas PH307 you can immerse yourself in luxe tropical comforts blended with blue ocean views. This delightful Maui ocean view vacation residence will cultivate long lasting memories and leave you feeling rejuvenated upon departure. Centrally located on...
Lovely Palms at Wailea condo, spacious, large lanai, close to beach! Full A/C
Located in the highly desirable Palms at Wailea, this delightful condo offers a relaxing retreat for guests. This spacious condo sleeps 4 with 1 bedroom featuring a king bed and a queen size sofa bed in the living room. It also has two full bathrooms. It's upstairs...
~ This Is Wailea Living ~
This is Wailea Living!Nestled in a private and secluded enclave between the Wailea Blue Course and the Wailea Tennis Club, the Wailea Grand Champions Villas are where travelers can golf, play tennis, be pampered at the Wailea Grand Spa, whale watch or turtle spot, or...
Wailea Beach Villas PH309 - 3 Bedroom Ocean View Penthouse
Penthouse 309 at Wailea Beach Villas offers a distinctive blend of luxury and cultural charm, making it an ideal vacation rental for families or groups of friends. This 2,520 square foot ocean view suite is located on the third floor and is accessible via a private...
Receive a $100 Gift Card for Snorkel Gear or Wailea Dining Options!
*Absolutely Stunning Panoramic Ocean and Island Views*Yards Away from Local Favorite Shops and Dining*4 beaches within 1-2 miles (Wailea, Ulua, Mokapu, Keawakapu Beaches) Experience paradise at Wailea Ekolu 104, where breathtaking panoramic ocean views and spectacular...
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...
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...
Amazing view, Close to the beach, Wailea Ekahi Unit 20i
Condo 1 bedroom, 2 bath (sleeps 4)PRIME location on the front row in lower Wailea Ekahi, Wailea. Listen to the sound of the waves and enjoy the ocean views. Famous Keawakapu Beach is just steps away! Beautiful ocean views from every room. Enjoy the extra-large lanai...
Impressive 2 Bdrm+2 Ba Paradise Condominium at Wailea Grand Champion Villas
Treat yourself to an impeccable Front-Row 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is the finest that Wailea Grand Champion Golf Villas has to offer in a 2 bedroom + 2 bath category. Upgraded in every way with split A/C...
Wailea Ekahi 14F - Best Views - 3 Minutes Walk to Beach
"Comfortable luxury with a magnificent view," wrote a recent guest. Wailea Ekahi 14F is an upper-floor 2-bedroom 2-bath condo. Situated in a quiet tropical garden setting in the center of Wailea Ekahi Village, far from road and pool noise, with one of the three "quiet"...
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...
Maui's Best - Wailea Ekahi 47A
Aloha and mahalo for your interest in our spot in Paradise. Ekahi says it all. This one bedroom (with comfortable sleeper sofa), two-bath renovated unit is on the ground floor. This means the lanai is much larger than upper units. It also means that when you step off...
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
RARE NOVEMBER OPENING - THANKSGIVING AVAILABLEThe 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...
Wailea Beach Villas PH402 - 2 Bedroom Ocean View Penthouse
Experience the very best in tropical island living from ocean view Wailea Beach Villas Penthouse 402. Revel in sweet sunsets and seasonal whale watching from your spacious, private lanai with scenic views of the Maui horizon, Molokini Crater and the island of...
On Wailea Blue Golf Course ⛳️with Ocean View. 🌊
Hawaii GE & TA Tax ID # G/T 006-824-3456-01 Taxes on total amount is 17.42%. Not included in the vrbo quote. Required is a signed rental agreement between guest and owner.This rental agreement is in addition to the deposit. After you initial and sign the agreement, it...
PURE ELEGANCE*OCEANVIEW Renovated Condo in WAILEA
For travelers seeking luxury and an escape from life in the resort town of Wailea, this complex is one of the most exclusive sanctuaries. The newly renovated 1536 square foot condo is a spectacular beachfront vacation rental with panoramic ocean views and extensive...
Wailea Ekahi Village 4D - Studio Garden View Condo
Wailea Ekahi 4D is a charming studio vacation rental perfect for the couple or solo traveler. This second-floor unit offers an elevated retreat with a bird\'s eye view of the surrounding tropical landscaping and peek-a-boo ocean views. The 600-square-foot condo is more...
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...
Wailea Ekolu #405 SUPREME OCEAN VIEW on Wailea Golf Course w/ FULL A/C
Introducing the newest unit in our portfolio! Please visit and be our first review with an introductory Special Rate till August 31th! Wailea Ekolu #405 is an ocean view 2 bedroom, 2 bath ground floor unit with air conditioning throughout, a fully equipped kitchen,...
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
The Maui Meadows Guesthouse Property is 3/4 mile from (8) premier beaches and features: (4) Bedroom, (5) Bath one story 2700 sq ft house, Proximity to beaches, activities, golf, shopping, restaurants and bars, Air conditioning, 65" TV screen with Streaming TV with NFL...
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 POINT...BETTER THAN THE GRAND WAILEA AT LESS THAN HALF THE PRICE!
The Best Property for the Best Price at this Exclusive World Class Destination!Make this beautiful condo your next vacation spot!!! Enjoy this gorgeous second floor unit providing a 90 degree view of the ocean. Hear the waves splashing on the sandy shores at night. You...
Wailea Elua Village 705 - 2 Bedroom Garden View Condo
Wailea Elua 705 is an exquisite vacation rental located on the stunning shores of Maui. This newly renovated, two-bedroom, two-bathroom beach house inspired condominium offers a spacious layout ideal for families or groups of friends seeking a luxurious getaway. With...
No stairs inside or out! Beautifully remodeled Palms at Wailea 503
NO STAIRS INSIDE OR OUT!Welcome to Palms at Wailea 503, your beautifully remodeled sanctuary in paradise! This is a two-bedroom two-bathroom condo in the prestigious Wailea Resort area. One of only three condos at the Palms at Wailea complex with NO STAIRS inside or...
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...
KBM Resorts | FREE CAR | Wailea Beach Villa | Spacious 3-Bedroom Condo with Sweeping Ocean view! WBV-PH412
** 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...
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,...
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...