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.
Spectacular Ocean Views! 5 Star Reviews! ʻIke Kai at Wailea Ekolu Village
Aloha!Welcome to our Our Maui Condo! ʻIKE KAI, which means "OCEAN VIEWS," offers a one-bedroom, two-bath, ground floor retreat that will delight even the most discerning traveler. Nestled in the desirable lower section of the Wailea Ekolu Village complex, our condo...
Only Steps to Ulua Beach and the main Wailea Ekahi Pool/Pavilion -1 Bd+2Ba
New A/C system, new bed and mattress, new furniture, new electronics. 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. Located directly on...
Ocean View, Steps away from the pool
"COVID-19: Dear travelers. Even though we have always maintained an exceptionally clean property, you can rest assured that we are following the guidelines of the CDC and Expedia/VRBO for enhanced cleaning and disinfecting of short term rentals. Additionally, the State...
'Best Vacation Ever' Say Our Guests! Special May Rates
You will love this luxurious, air conditioned, two bedroom, two bath, 1300 square foot Villa! Fully furnished, with its own spacious, private dining lanai, this unit was completely remodeled in 2020. It is immaculate, impeccably maintained and cleaned to the highest...
Luxury at its Best with Big Ocean Views!!
Aloha & welcome to the Wailea Diamond Suite at Ekolu Village #305!The moment you step through the door you’ll know you’ve come home to luxury in this elegant 2 bedroom, 2 bath condo. Each bedroom features its own unique bath, private lanai sanctuary, ambient...
Polo Beach 808! Unique opportunity one-bedroom, top floor home.
Unique opportunity to stay in a one-bedroom, top floor home at one of the most desired properties on Maui. Polo Beach #808 will be your favorite place to stay when visiting the island. Top floor, corner unit with EXQUISITE VIEWS of the Pacific Ocean, Molokini,...
Fully Remodeled Elegance in Wailea 2Bed 2Bath
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 Wailea town, our villa complex exudes charm, luxury, and allure.Nestled within the exclusive town of Wailea,...
FULL OCEAN VIEW WAILEA
Bright airy updated large 1 bedroom 2 bath top floor in sought- after Wailea Ekahi Village. 27D is a top corner unit known for our panoramic ocean views. Enjoy a Mai Tai while gazing out at the whales breaching out of the ocean at sunset! This unit boats high ceilings,...
Enjoy garden views and ocean glimpses from your private lanai at #138
Location! Location! Location! Who needs a car?!? This central Wailea location makes it favorable as you can find tennis, golf, retailers at the Shops at Wailea, casual to fine dining restaurants, world's top beaches, and five-star hotels just moments away.Kick back and...
Stunning Ocean View Wailea Beach Villa- Book & Save
Most popular Maui Condo Wailea Beach Villa L409 Rated Perfect . 4BR (3 Kings/1 Queen, or 2 Kings/ 2 Twins/1 Queen) 3 BA villa . Spectacular panoramic ocean view. This elegant 4th Floor Villa is nestled between The Grand Wailea & The Shops at Wailea. Almost 3000' with...
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...
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...
Exquisite Oceanview Villa with Resort Amenities in Gated Community
This property is hotel zoned, and not being affected by the recent proposed legislation.Located in highly desirable secluded area of neighborhood your villa welcomes you with spacious floor plan and sweeping ocean views. Marvel at the beautiful Maui sunsets from your...
Wailea Beach Villas | PH410
Wailea Beach Villas PH410 is a fourth floor penthouse suite that overlooks the central swimming pool with spectacular views of the Pacific Ocean and Wailea Beach, along with views of Kaho’olawe, Molokini and Lana'i.From your private elevator landing, the suite opens...
Wailea, Oceanfront, Polo Beach Club Condo #403
Location, location, location…. Polo Beach is the premiere condominium that sits at the south end of the Wailea Beach walk, next to the Fairmont Kei Lani resort. Our unit is on the sunny south side of the building, overlooking the pool area and ocean, and south towards...
Gorgeous Wailea Elua 2Bd+2Ba 1st Floor, Ocean View Paradise Condominium #2301
New living room furniture and lanai furniture - Absolutely Lovely! Wailea Elua Village #2301 is a premier vacation condominium located in Elua Village which is directly on the sugar sand of Ulua beach in Wailea. This impressive vacation condominium is constantly in high...
Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4
Newly Remodeled in 2023! Come relax and enjoy the spectacular ocean and island views in this rare three bedroom condo perched on the very top row fourth tier in the Ho’olei community.This spacious unit has 3 bedrooms, 3.5 bathrooms, a large living room, fully equipped...
Beautiful Sunsets with this Ocean View Condo! Mar 23 - April 7 Open!
This beautiful top floor, Grand Champs condo has one of the best ocean views in the complex. This fully updated 2 bedroom, 2 full bath condo has wonderful panoramic ocean views perfect for sunsets and whale watching. From the extra large, newly tiled lanai, you can see...
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...
Wailea Beach Villas | PH309
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...
Fantastic unit! 10/10! Hear the waves from the lanai! 1 bedroom unit. Sleeps 4
This one bedroom, smoke-free condo, is located in Ekahi Village, and is a short (less than 4 minutes) relatively flat walk to the beautiful Keawakapu Beach. The unit is located in the lower village. You can stay on the beach for the day or enjoy the amazing new...
Luxurious Ho'olei Villa with Ocean Views, Two Story Townouse!
Stay longer, enjoy more! Book 10+ nights and receive a free mid-stay clean. Book 14+ nights and get one night free!This property is hotel zoned, and not being affected by the recent proposed legislation.Welcome to this luxurious Ho'olei Villa with amazing ocean views!...
Tiki Tiki - A Gorgeous Boho Beach Hideaway!
Fall in ALOHA with Tiki Tiki!! This special studio is truly a piece of Paradise!A magical retreat that will have you feeling zen & refreshed. Tiki Tiki is the perfect home for honeymooners, girlfriend getaways, or any adults looking for a tropical stay in the the heart...
🐬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!...
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. Gorgeous! Stay with Wailea Rentals at Wailea Ekahi Village 20G and you and your guests will enjoy premier accommodations, furnishings and holiday experiences at this...
125+ 5star REVIEWS SAYS IT ALL! Golf & Ocean! LAST MIN CANCL APRIL! 169 +tx rate
Location: Grand Champions, Wailea, South Maui, Maui, Hawaii, USA (2 miles Kihei, 13 miles airport, 1/2 mile beach.) Accommodations: Condominium, 1 Bedroom, 2 Baths (Sleeps 2) Maximum occupancy is 2 adults 25 years old or older onlyCOME ENJOY OUR FULLY RENOVATED FROM...
Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!
Enjoy the exclusive Wailea lifestyle in this fashionably decorated, high-end suite with incredible ocean views!!!---This gorgeous, bright and spacious 1-bedroom, 2-bathroom top floor unit offers unmatched views of the ocean and the scenic Wailea greenbelt area. This...
STUNNING NEW REMODEL-SUNSETS-LUXURY-QUIET LOCATION-AC-LARGE LANAI
Book with confidence, this stunning, 1 bedroom, 2 bathroom (1022 sq. ft) condo that has been completely remodeled from top to bottom with modern finishes, where even the lanai sliding doors were replaced. This condo is managed by PMI Maui, a local Real Estate Brokerage...
Wailea Elua 3 Bedroom+2 Bath Spacious Beach Home with Oceanview Lanai
This is the one! A real Maui home-away-from-home. If you are looking for an impressive vacation home with new Ohia wood cabinets, cupboards, and accents in the kitchen, new sandstone tile flooring, super quiet new Fleetwood glass doors, new Miele appliances, and new...
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...
Stunning ocean view! 2/2 in the heart of Wailea
Halloween Special! 20% off all days October 28 - November 5!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...
Stunningly Renovated! Ocean View! Elua 2305
This property is hotel zoned, and not being affected by the recent proposed legislation.Welcome to Elua 2305. Your ultimate Maui vacation awaits at this fabulous listing! Don’t miss this incredible opportunity to enjoy the very best that Maui has to offer.Say Aloha to...
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 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...
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
**FAMILY FRIENDLY**If you are looking for a modern, luxurious retreat in Wailea with BRAND NEW EVERYTHING, look no further! This unit was completely gutted to the studs and every item was purchased brand new. Guests can enjoy:— Modern, deluxe kitchen with all new...
Polo Beach Club | 409
Polo Beach Club 409 is a luxurious oceanfront vacation rental located in the world-renowned beach vacation destination of Wailea. This two-bedroom, two-bathroom condo offers a premium beachfront experience with direct access to Polo Beach out front and stunning ocean...
Immaculate, Luxury Comfort, Stunning Views - Hawaiian-Chic, Mid-Century Modern
Experience the beauty of Wailea from the moment you arrive in your spacious and stylish villa. Situated in a secluded position of the Grand Champions resort property you can relax on the lanai and take in the views, get to that book you’ve been meaning to read, or...
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...
nNEW KITCHEN REMODEL! Amazing View!
Condo, 1 bedroom + other (See Description) 2 baths (Sleeps 4)Peace of mind is important for where you are staying. Our cleaning care professionals have been trained to properly follow all CDC, VRHP (Vacation Rental Housekeeping Professionals) and VRMA (Vacation Rental...
NICELY UPDATED-SLEEPS 8-WELL EQUIPPED-AC-METICULOUS CLEANING
Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that has been nicely updated. 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...
The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
The Maui Escape is located with views of the upper pool and the spectacular surroundings. The villa's location is the perfect combination of being close enough to view the pool but far enough for privacy. At night the ambiance from the lanai is breathtaking with...
NEWLY REMODELED-QUIET LOCATION-AC-WELL EQUIPPED-METICULOUS CLEANING
Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that was just completely remodeled with all new furnishings. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of...
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...
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...
Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025
Remodel completed June 2025! See the new photos just posted!The entire home has been repainted, almost all the furniture was replaced, a lot of new beautiful art was added, and all new hardwood French oak floors were installed in the bedrooms.. We also remodeled the...
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...