Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui

Wrap-Around Ocean Views | Wailea Beach Villas PH301

Wailea Beach Villas Penthouse 301 offers an unparalleled vacation experience with its luxurious 2,500 square foot ocean view suite. Situated on the third floor and accessible via a private elevator, this penthouse ensures privacy and tranquility. The suite features...

Cool Wailea Villa with Arcade Machine

Indulge in entertainment abound when vacationing in Wailea Beach Villas Penthouse 211. After you've spent an action-packed day at the beach or hiking one of Maui's scenic trails, return to your vacation residence and discover some more relaxing entertainment options...

Wailea Beach Villas PH112 - Professional Managed

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...

Fairway + Pacific Ocean Views | Wailea Ekolu 910

Discover the perfect Hawaiian retreat at Wailea Ekolu Village with this stunning two-bedroom, two-bathroom ocean view rental. This premium condo offers breathtaking views of the Pacific Ocean, Kaho\'olawe, and Molokini from its private lanai. Ideal for families or small...

Beachfront Condo - Steps from Wailea Beach Path

Polo Beach Club 206 is a second-floor vacation rental located in the renowned Wailea area of Maui. This condo offers a prime beachfront experience with direct access to the pristine Polo Beach directly in front of the property, making it an ideal choice for those...

Wailea Elua 805 - 3-Bedroom Ocean View Luxury Condo in the Heart of Wailea, Maui

Welcome to Wailea Elua 805, a beautifully remodeled 3-bedroom, 2-bathroom vacation rental located in the exclusive, gated beachfront community of Wailea Elua Village on Maui's stunning south shore. Just a two-minute stroll to Ulua Beach, one of Wailea's top snorkeling...

Wailea Ekahi Ocean View Studio! AC included

Experience Island Elegance at Wailea Ekahi Village 15EWelcome to your serene retreat in the heart of Wailea! Unit 15E is a fully furnished, turnkey studio condo offering the perfect blend of comfort and island charm. Situated on the desirable greenbelt of Wailea Ekahi...

Wailea Elua 702 - Beautifully Renovated, Stunning Ocean Views, Central AC, Wi-Fi

Welcome to Wailea Elua Village 702, your perfect island retreat! This beautifully remodeled 2-bedroom, 2-bath ocean view condo offers an unforgettable stay in the heart of Wailea, Maui. The master suite features a king bed and a private ensuite bath, while the guest...

The Best Condo in Wailea Ekahi Village!

Wailea Ekahi Village is a tropical oasis that sits right on Ke'awakapu Beach, considered by locals to be Maui’s best beach. Surrounded by major resort hotels, shopping centers, and championship golf courses, it's a vacationer's dream! This condo is in one of Ekahi...

Wailea Ekahi Gem! Remodeled Large 1BR+sleeper, Close to Beach & Pools, XL Lanai

Experience Maui paradise at Wailea Ekahi 21B, a fully renovated ground-floor one-bedroom/two-bath vacation condo nestled within the prestigious Wailea resort district. This beautiful unit showcases a designer remodel, offering a spacious, modern, and bright atmosphere...

PAW 1706 Remodeled Wailea Condo w Pool AC Near Beach

Palms at Wailea 1706 Beautifully Remodeled 1Bedroom Wailea Condo with Pools, AC Throughout, Spacious Furnished Lanai, Close to White Sand Beaches, Near Dining and Shops Welcome to your next Hawaiian getaway at Palms at Wailea! This spacious and beautifully remodeled...

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...

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...

Beautiful Palms at Wailea Condo!

Escape to paradise at The Palms at Wailea Hotel & Resort! Our Mediterranean-style condo rental is nestled on a hillside, offering breathtaking views from the 2 porches! This unit accommodates up to 4 guests, complete with access to a community pool, hot tub, and...

MauiTime at Wailea Ekahi, easy walk to beach, dining, shopping, 4 pools plus...

ALERT: Beginning Jan 1, 2026 the State of Hawaii Transient Accommodation Tax (TAT) goes to 11% from 10.25%It’s great to be alive in 2025!So many rumors surrounding Maui Vacation Rentals. The truth is Maui is open and ready for your business with the spirit of Aloha!In...

Luxurious Oceanfront Condo at Wailea Elua Village - Unit 1201, Central AC, Wi-Fi

Wailea Elua 1201 is perfectly positioned in the coveted interior courtyard, 39 steps to famous Ulua Beach, perennially named as one of the world's top 10 beaches and one of the best snorkeling reefs on Maui. This ground floor condo features an oversized, shaded...

Family-friendly condo near Kihei and Wailea

Maui Vista 2413 is a two-story, 2-bedroom, 2-bathroom condo offering amenities like air-conditioning, a washer/dryer, and a private lanai. Located on the fourth floor, this spacious unit accommodates up to 7 guests, featuring a California King bed in the master bedroom,...

Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!

Boasting stunning panoramic views of the Pacific Ocean that extend deep into the home's living, kitchen, and dining areas, Wailea Elua 2204 is a luxuriously renovated second-floor villa featuring some of the most spectacular vistas South Maui has to offer. Watch...

Direct Ocean Front Property Wailea Ekahi 42A Remodeled 2024 - 1 Bed 2 Full Bath

Imagine waking to the gentle lull of the trade winds, sunlight streaming through your lanai, and the promise of a perfect day in paradise. Welcome to Unit 42A at Wailea Ekahi Villas, a meticulously remodeled one-bedroom, two-full-bathroom haven where luxury meets...

Wailea Ekahi 4E, Bordering Private Tropical Greenbelt, Split AC and Beautiful!

Welcome to Wailea Ekahi 4E, a serene one-bedroom, one-bathroom retreat nestled in the heart of Maui's lush Wailea coast. Perched on the second floor of a low-rise building, this corner unit offers a private and peaceful setting, surrounded by tropical greenery and just...

Maui Designer Beach Villa, Wailea, Ho'olei 39-2

Welcome to Your Pristine OasisIndulge in the lap of luxury at this exquisite 3,400-square-foot vacation rental villa (Ho'olei, Maile floor plan). Nestled within the prestigious Ho'olei Community in the enchanting town of Wailea, Maui, this immaculate property promises...

Luxurious & Spacious Ground Floor Gem with Panoramic Oceanview - Wailea Elua 305

Wailea Elua #305 – Stunning Ocean View Retreat with Luxury Comforts and Designer FinishesExperience the elegance and serenity of Wailea Elua #305, a spacious 2-bedroom, 2-bathroom condo beautifully redecorated with high-end furnishings and panoramic ocean views. This...

New Listing, Wailea Ekahi Village 5F, Close to Oceanfront Pool Pavilion on Keawakapu Beach

Summary:Ocean Breezes & Maui Magic: Wailea Ekahi Village Unit 5FThe Space:Prime Location & Ocean Vistas: Escape to Maui's paradise at Wailea Ekahi Village unit 5F. This charming 2-bedroom, 2-bathroom condo boasts a prime location near the beachfront pool, pavilion, and...

Wailea Ekahi 1C - Wonderful 1bd/1ba / Close to the Beach / Sleeps 5

Oceanfront complex, one-bedroom, one-bath, single-level, ground-floor corner unit.Quiet location. No traffic noise (you are in paradise, there should be none). The condo is located in the 'Lower Village' just steps from one of the 3 quiet pools, close to the beach and...

Spacious Wailea Townhouse + Ocean Views! Ekahi 48A

Welcome to Wailea Ekahi 48A, offering the largest floor plan with gorgeous ocean view! This beautiful 2 bedroom/2.5 bath is the perfect retreat for couples or families. The first level of this spacious condo features a sunken living room complete with convertible queen...

Ocean Views & Modern Aloha Luxury in Heart of Wailea

Welcome to our Ohana. The Hawaiian word "Ohana" means family and embodies the spiritual quality of kindness and love for all of the human family. Our Ohana offers a modern gourmet kitchen, and a living area that is welcoming, bright and airy. Feel the ocean breeze on...

Beautiful 1 bedroom condo. Private ocean-view lanai overlooking fairway!

Grand Champions 1-bedroom on Wailea Blue Course with Private Lanai, Ocean Views!Welcome to paradise! At a time when there was much uncertainty in the world, we made a big decision to purchase in May 2021, as our lifelong dream is to snowbird in Maui. Until that time...

Private and Sweet Wailea 1 BD+2 BA Grand Champions Villa

New Furniture! New personal amenities! new soft goods! Unit #54, building 6. An impeccable 1 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. Wailea Grand Champions Golf Villas is in the heart of the Wailea Resort Community in sunny South...

Private House on Maui / 3 Bedrooms / 5MIN to Beach /UPGRADED Wailea / Kihei HI.

FIVE STAR REVIEWS FROM OUR GUESTS GIVES YOU THE ASSURANCE OF QUALITY.A FULLY EQUIPPED PRIVATE BEACH HOUSE WITH EASY ACCESS TO ALL ATTRACTIONS, BEACHES RESTAURANTS, SHOPPING ETCALSO, WE NOW OFFER A 'PEACE OF MIND' FULL REFUNDED FOR YOUR RESERVATION. (conditions apply see...

Spectacular Ocean View & All-Season Sunsets from Private Lanai Wailea Ekolu 1704

Aloha,Welcome to our family gem, location Wailea Ekolu Unit 1704. Our 1070 square foot spacious condo with private lanais, has been a family treasure since it was purchased new in 1979. Newly renovated and restored to its original vintage condition, the condo has been...

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...

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...

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...

Wailea Elua Top Floor 2 Bdrm/2 Bath Oceanview Unit - 1 min walk to Ulua Beach

6th night free! discounts applied when booked. offer good until Dec 15th, 2025.Roomy and relaxing top floor 2 bedroom + 2 full bathroom vacation condominium steps to the beach and pools with convenient parking. Recent upgrades make this a welcome vacation-home where,...

Relaxing Wailea Ekahi Garden Hideaway.

Wailea Ekahi 47F is surrounded by lush gardens, offering guests a private hideaway to relax while being serenaded by birds. Our unit is a five minute walk to the sparkling sands of Keawakapu Beach. You'll stroll through Wailea Ekahi's lush gardens on paved paths enroute...

Stunning One Bedroom in the Heart of Wailea Ekahi Village Unit 28B

Listen to the waves calmly lap against the shore as you drink your coffee on your own private lanai. Enjoy cooking your favorite meal in a newly renovated kitchen equipped with stainless steel appliances, custom cabinetry, and granite counter tops. Your unit is filled...

Wailea Grand Champions #157 Great views, Free high speed Internet & Free parking

Why stay in Lahaina or Kihei when you can Vacation in a fabulous condominium on the sunny south coast of Maui. Located in the lush Wailea resort area, this Grand Champions air-conditioned villa is located on the second fairway of the Wailea Blue Golf Course with a...

Wailea Ekahi 45B-Great Rates,Lovely New Kitchen, Large Lanai, Pool #3 w/BBQ

Unit 45B is located in Building 45 on the ground floor. This lovely one bedroom, two bathroom condo has a 400 square foot lanai with picturesque garden and ocean views and Quiet Pool 3 just steps away. Patio equipped with spacious patio seating & chaise lounge. This...

Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean and Sunset Views

Location and views are everything when it comes to this home. Only a short walk to some of the most beautiful beaches in the world. Nestled in the heart of Wailea, most would consider to be the most beautiful and prestigious area of Maui. This RARE 3 bedroom villa has...

Palms at Wailea 902 - Luxuriously Decorated, Spacious, and Very Private & Quiet

Hawaii Tax ID: TA-144-497-4592-01 QUIET PRIVACY IN PARADISE - BEAUTIFUL GARDEN/OCEAN VIEWSThe Palms #902 is a luxurious one-bedroom two-bath upstairs villa tucked away in a private and quiet corner in one of the nicest locations on the property. The unit has a beautiful...

Panoramic Ocean View Wailea Ekahi 34D overlooking Ekahi's lush greenbelt

Wailea Ekahi 34D is located in the lower village, on the greenbelt, with direct views of the ocean, Molokini and Kaho'olawa. This condo has been completely renovated from the studs in. Furnished with high end furniture, fixtures and decor in an Asian flair, this condo...

Wailea Ekahi 51F Oceanview - Walk to Beach

Our spacious Wailea Ekahi 1 bedroom, 2 bath condominium is fully appointed and includes phone, radio, high speed wi-fi internet connection, color TVs with DVD and cable, private laundry center and personal touches for your enjoyment and convenience.There is a fully...

1 BR Treetop Wailea, 2nd floor vaulted ceilings

The Tree Top One Bedroom, is an elegant, bright 2nd floor unit with tropical modern king bedroom, teak and rattan furnishings, spacious bath with separate shower and tub, spacious living/dining area and well stocked kitchen and offers privacy amid tree top blooms and...

Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

One of a kind four bedroom Ho'olei home in Wailea!Breathtaking is the best word to describe this luxury townhouse-style villa at Ho’olei, situated in beautiful Wailea on the sunny, southwestern shore of Maui. Ho’olei is the ultimate dream home in paradise!This recently...

Stunning Luxury Remodel I Wailea Beach Villas J206

Wailea Beach Villas is simply the best of the best! Enter the community through the 24hr private guarded gate & drive down to the complimentary self parking in the indoor garage. Check-in and receive your key card from the lobby you'll be able to access your own...

Wailea Ekolu 703 / Beautiful Ground Floor, Expansive Lanai, Ocean Views & Aircon

Indoor outdoor living with Fantastic Ocean views from this spacious 2 bed/ 2 bath ground floor private condo! Enjoy early morning walks or a relaxing dip in the pool. This unit has been completely remodeled from top to bottom, all new windows and double pane sliding...

Escape to Paradise – Your Dream Wailea Getaway Awaits!

Welcome to your tropical retreat at Grand Champions Villas in Wailea, where luxury meets tranquility. Imagine unwinding in the hot tub while watching the breathtaking sunset over the Pacific, or recharging with a delicious dinner on your private lanai as the evening...

Ocean & Golf Views in Wailea - Designer 2 Story Condo w/ AC system, Wifi

The Address to Wailea Ekolu #314: 10 Wailea Ekolu Pl. #314 Kihei HI 96753*Professionally Cleaned Condo, No-Contact Check-In/Check Out*Location & luxury combine to make this Wailea Ekolu condo a perfect home away from home. Only minutes from Maui’s best beaches, high-end...

Wailea Ekolu Oceanview 2B/2B ocean view, ground floor unit, corner unit

ENJOY THE BEAUTIFUL MAUI SUNSET! Sharon's spacious, 1,400 square foot Wailea Ekolu condominium is a two bedroom, two bath, ocean view unit. Located on the ground floor, it is surrounded by grass and lush island foliage. The condo accommodates four people comfortably....

Palms At Wailea 1801, 2Bd 2Bath, FULL AC, Sleep 6, New Owner, Renovated,

The fabulous Keawakapu Beach is just a short 10 min stroll. The Palms at Wailea is a gorgeous property with a large pool and hot tub. A magnificent view of the ocean from the pool area. Unit #1801 is a spacious 2 bd, 2 ba ground floor unit. It has a fully-equipped...