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.

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Fabulous Ulua Beach & Lush Grounds Await: Wailea Elua 807, Groundfloor Gem!

Wailea Elua #807 – Ground-Floor Serenity with Ocean Breezes and Refined ComfortWelcome to Wailea Elua #807, a beautifully appointed ground-floor, 1-bedroom, 1-bathroom condo designed for peaceful and private escapes in one of Maui’s most exclusive beachfront...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 2
📍 Wailea, Hawaii

Wailea Ekahi 17E | Resort Level Amenities!

The beauty of sand and sparkling waters and the warm Hawaiian sun is calling your name! Wailea Ekahi 17E is a one bedroom, two bathroom condo that sleeps two guests. Take in the ocean view, enjoy the 34 tropical landscaped acres at Wailea Ekahi Village, Keawakapu Beach,...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 2
📍 Wailea, Hawaii

Wailea Grand Champions | 75

Wailea Grand Champions 75 is an exceptional vacation rental situated in the picturesque Wailea region of Maui. This luxurious property promises an unforgettable escape with its blend of elegance, comfort, and stunning natural beauty.Upon entering Wailea Grand Champions...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekolu Village | 1205

Wailea Ekolu 1205 is a two-bedroom, two-bathroom ocean view vacation residence that comfortably accommodates four people. The sweeping ocean views beyond the Wailea Blue Golf Course and lush tropical landscaping make this private vacation home feel truly idyllic.The...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Grand Champions 108 | Sunset Views + Amenities

Grand Champions 108 stands as a beacon of refined luxury in Wailea, Maui. This meticulously remodeled one-bedroom, two-bathroom villa offers an unparalleled retreat, blending contemporary elegance with island charm. Perched atop an elevated lanai, the villa presents...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 2
📍 Wailea, Hawaii

Ocean Views + Exquisite getaway Wailea Ekahi 53D!

Special Offer: Book 8 or more nights, get 1 night free or Book 12 or more nights, get 2 nights free. Valid on all new reservations booked on or after 10/17/2024.This exquisite, second floor, 1bedroom, bathroom retreat is the perfect Hawaiian getaway. With gorgeous views...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

360 Premier Ocean View! Remodeled Ekolu # 1510!

This is a premier unit with panoramic ocean views located just minutes to all Wailea Beaches, The Shops at Wailea and Luxury Hotels! This beautiful condo is fully remodeled with tasteful furnishings, top of the line appliances, exquisite cabinetry, upgraded bathrooms...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Stunning Remodeled Unit with Ocean Views! Ekahi 5E

Welcome to Ekahi 5E! This top floor unit boasts incredible ocean and garden views! It is nestled along a beautiful hillside that embraces the serenity and peacefulness of Maui. Enjoy the views and feel the breeze from the oversized private lanai! Your private lanai...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 3
📍 Wailea, Hawaii

CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

DISCOUNTED RATES FOR LAST MINUTE OPENINGSWe appreciate your support as a small, self managed Maui family owned rental instead of renting from a large mainland management company. Experience island life in our luxury, spacious, one bedroom condo. Unit #22 is on the top...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Private Lanai with Ocean Views! Updated Furnishings! Polo Beach 203

Relax on the lanai and enjoy sweeping views of Molokini and Kahoolawe Island at sunrise or sunset. Stroll along the world-famous Wailea Beach Path, enjoy fantastic snorkeling at uncrowded Polo Beach, or unwind and sunbathe at the oceanfront pool and jacuzzi.Spend a...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village | 15D

Welcome to Wailea Ekahi 15D, a stunning one-bedroom, one-bathroom vacation rental nestled in the heart of Wailea. This second floor vacation condo features a covered lanai along the lush greenbelt that terraces between buildings and leads down to the ocean. Partial...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Walk to white sandy beaches - Palms 501

This beautiful, tropical two-bedroom/two-bath condo is just a short 5-minute walk from the world-famous Keawakapu Beach!! Enjoy dreamy sunset strolls along the golden sands or start your day with a peaceful jog through paths lined with lush tropical flowers. Dive into...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Island Luxury at Wailea Elua #302: Expansive Ocean Views and Gorgeous Interior

Wailea Elua #302 – Top-Floor Ocean View Elegance with Artistic Hawaiian TouchesWelcome to Wailea Elua #302, a stunning 1-bedroom, 2-bathroom top-floor end unit located at one of the highest vantage points in the community. This beautifully updated condo features...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Prime Wailea: Split AC, Wailea Ekahi 36E

Wailea Ekahi 36E offers the perfect Hawaiian retreat! You will enjoy this second level condo surrounded by tropical foliage. The private lanai offers a relaxing space with floor to ceiling sliding glass doors, indoor/outdoor living is seamless. Wailea Ekahi no longer...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Makena Surf | E105 | Beachfront Resort

Welcome to Makena Surf E105, your ideal oceanfront getaway nestled within the luxurious Makena Surf resort, located on the pristine Po'olenalena Beach. This secluded beachfront property offers the ultimate in tropical island relaxation, making it the perfect retreat for...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Ekolu Village | 912

Wailea Ekolu 912 is a delightful one-bedroom, two-bathroom vacation rental that offers stunning ocean views and a relaxing retreat in the heart of Wailea. This beautifully designed condo features many eye-catching design elements, including wood paneling on the vaulted...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 2
📍 Wailea, Hawaii

Wailea Ekahi Village | 3A

For a vacation condo that feels like a private home, select this two story residence with a sunken living room and cascading lanai. Four sets of sliding doors on the first floor provide garden views and invite tropical breezes into the open floor plan. The walk-through...

🛏 2 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Top Floor Remodel! Ocean & Fairway Views Ekolu 908

Beautiful and completely remodeled! The moment you walk through the front door, you will be mesmerized by the views and the beautiful upgrades! This top floor unit features a gourmet kitchen with granite counter tops, stainless steel appliances, custom made cabinets and...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 5
📍 Wailea, Hawaii

Wailea Ekolu 1403 -1 Bed/2 Bath Vacation Condo

Fresh new upgrades - new king bed, new wood flooring, new TVs, kitchen appliances, window blinds, lighting, and two comfortable lanais with an outdoor lawn area. New refrigerator, stove, dining room table, barstools, window shades, new linens and towels. We also have...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Updated, private home with serene fairway views. Modern comfort in paradise!

Newly updated home with privacy and serenity. Tucked amongst the tropical foliage, in the far corner of the property, overlooking the fairway of hole #3 of the Wailea Blue Golf Course, Grand Champions #30 is a mix of peaceful tranquility and modern comfort. Fresh paint,...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 7
📍 Wailea, Hawaii

April Special: Beautiful, Palms At Wailea Condo #608- 2BR/2BA,Great Location!

The Aloha Spirit is Alive and Well in Maui! It's absolutely beautiful. The best beaches , clean air, amazing sunsets, rainbows, humpback whales and wonderful hiking, along with the best restaurants. The people are the best! Lahaina is gone but memories will always be...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Luxury 2-bedroom with ocean & fairway views, upgraded and beautifully decorated

Luxury awaits you in this beautifully upgraded 2-bedroom condo. Magnificent ocean and fairway views from this beachy unit with 1,056 square ft of living area and bonus lanai space. This is truly a beautifully remodeled and decorated unit!Once you enter this condo, you...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Polo Beach Club 305, you will be drawn to the breathtaking views from lanai.

Polo Beach 305, with Spectacular Ocean Front Views! Located in the highly sought after beachfront stack. Take in an unforgettable sunset or views of Kaho'olawe, Molokini, and The West Maui Mountains!As you enter Polo Beach Club 305, you will be drawn to the breathtaking...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Grand Champion Golf Villa 2 Bdr/2 Bath

Spring and Summer Special - Sixth Night Free! Each 6th night free! On all new reservations for nights between April 1, 2025, and August 31, 2025. Call or email for details. Discount applied to final payment and not to be combined with any other promotions. Comfortable...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Beautifully Renovated Grand Champions! Ground Floor! Grand Champions 139

Incredible Renovation! Kick back and relax on your own private lanai and take in wonderful garden views, with some ocean and mountain views. Feel the wonderful trade winds and take in the aroma of the beautiful Plumeria trees and Hawaiian foliage. This spacious...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Golf course-front condo with outdoor pool, hot tub, central AC, & free WiFi

Wailea Grand Champions 149Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy your very own paradise on earth at this family-friendly, golf course-front condo! It's perfect for a...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village | 11A

Wailea Ekahi 11A offers a truly exceptional and luxurious island getaway on Maui. Situated in the prestigious Wailea resort community, this spacious and elegantly-appointed condo provides the perfect balance of upscale amenities and serene tropical ambiance. As you step...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Redesigned 1BD/2BA condo with Haleakala views, near Wailea's beaches + dining

Grand Champions 136 is situated in a lush tropical setting. This 1 bedroom / 2 bathroom is located on the top floor with wonderful views of Haleakala. This condo is newly redesigned and furnished. It is the perfect setting for couples and small families. Its convenient...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Elua Village | 2008

Wailea Elua Village 2008 is a luxurious vacation rental situated along the southern coastline of Maui in the desirable Wailea region. This elegant condo offers a serene retreat for travelers seeking a blend of comfort and natural beauty. The interior of this one-bedroom...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Grand Champions | 27

Nestled in the heart of Wailea, this charming Grand Champions residence offers a tranquil retreat that feels like your own private Hawaiian sanctuary. As you step through the door, you're immediately embraced by the warmth of island living and the thoughtful design that...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Ocean views, pool, spa, and golf course nearby - Your Perfect Maui getaway.

Views of the ocean, a relaxing pool and spa, and a tropical landscape that is within minutes of beautiful sandy beaches make Wailea Grand Champions #122 the perfect home base for your island vacation. Abutting the fairways of the award-winning Wailea Blue Golf Course,...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 2
📍 Wailea, Hawaii

Wailea Ekahi Village | 3B

Nestled among the lush, tropical landscape, this studio is a perfect place to escape the hustle and bustle. Bring along that novel or take a refreshing nap after a day at the beach on the private lanai, secluded by tropical flowers. A writer's retreat!Recently renovated...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

Wailea Ike by AvantStay | Walk to the Beach | Balcony w/ Views

Pack your swimwear and prepare for an unforgettable getaway at this newly renovated condo, where every morning greets you with stunning balcony views of lush landscapes rolling down to the ocean. This condo is within walking distance of the beach, the Wailea shops,...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Grand Champions 87 ocean-view condo with pool, hot tub & washer/dryer

Wailea Grand Champions 87Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Newly and beautifully remodeled from top to bottom, this golf-course-front condo in the heart of Wailea will...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village | 9A

Welcome to Wailea Ekahi 9A, a charming vacation rental nestled in the heart of Wailea. This meticulously maintained one-bedroom, one-bathroom condo offers a perfect blend of comfort, style, and convenience, making it an ideal retreat for couples or small families...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Grand Champions 68! Enjoy stunning golf and ocean views from this inviting condo

Grand Champions 68! Beautiful golf and ocean views.As you enter you will be greeted by the charm of this condo! Open and inviting! Floor to ceiling sliding glass doors lead to your private lanai. Take in the tropical setting overlooking the golf course and ocean views...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Updated Wailea Condo in Oceanfront Complex!

Enjoy your open and airy living area with breathtaking views of the picturesque foliage through your lanai door in unit 52A! Ample seating available as the dining table for four and two seats at the bar area provide comfort and relaxation as you entertain family and...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Elua Village | 1303

When vacationing in Wailea Elua 1303, you’ll feel pampered by the extra touches that await you in this suite featuring modern comforts throughout. For example, readers will enjoy the owner’s book selection and the individual, overhead reading lights in the master...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village | 4B

Wailea Ekahi 4B is a charming ground-floor vacation studio nestled on a gentle slope in the picturesque Wailea Ekahi Village. This island hideaway offers a unique blend of accessibility and privacy, featuring a secluded back lanai enveloped by lush treetops, creating an...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

Beautifully decorated! Very private! Partial Ocean View! Palms at Wailea 2202

The main living area boasts expansive high beam ceilings that add to the wonderful flow of air blowing in off the Shores of Maui. Very spacious and open, bringing the outdoors into your living room and kitchen! This unit is situated in the highly sought-after complex....

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Ekahi 48C ~ 1 Bedroom 2 Bath Wailea Condo!

Wailea Ekahi Village - Spacious one bedroom, two bath condo with a enchanting garden view located in the Upper Village. New carpet throughout the unit. Master bedroom boast a King size bed. Plus there is a bonus sofa sleeper in living room. Full size washer/dryer, air...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Amazing! Beautifully remodeled and upgraded! Palms at Wailea 403

This cool, ground floor condominium is the most spacious 1200 sq ft two-bedroom 'C' plan, with sunken living room, brand new designer furniture, and extensive travertine and granite surfaces. Oceanic Time Warner cable, internet, phone, and Wi-Fi.Both kitchen and living...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Grand Champions 144 | Tropical Golf Resort w/ Pool

Whether you are looking for a relaxing getaway or seeking adventure of all kinds, Maui is the perfect vacation spot! Grand Champions 144 is a three bedroom, two bathroom condo that sleeps six guests. Enjoy the incredible primary bathroom, the private balcony with...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Prime Wailea Location! Split AC! Wailea Ekahi 36E

Wailea Ekahi 36B is a great ground floor location with lush garden views. This 1bedroom/2 bath condo offers the perfect Hawaiian retreat!Welcome to Ekahi 36B! This lovely condo offers everything you need for your Hawaiian Holiday! You will fall in love with this garden...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village | 40F

Discover the charm of Maui from the comfort of Wailea Ekahi 40F, a beautifully appointed one-bedroom, one-bathroom condo located in the desirable Wailea community. This inviting vacation rental combines modern amenities with a touch of tropical elegance, offering a...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village | 44B

For travelers seeking a budget-friendly option in the prestigious Wailea area without sacrificing comfort or location, Wailea Ekahi 44B presents an attractive choice. It is a charming studio provides a traveling couple or solo traveler everything they could need and...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Elua Village | 1501

Wailea Elua Village 1501 is the perfect home base for exploring the sights, sounds, and tastes of Maui. This two-bedroom garden view vacation rental is a short drive to the top Wailea and Kihei beaches for snorkeling, favorite restaurants on the south-side of the...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Grand Champions | 116

Wailea Grand Champions 116 is a luxurious vacation rental located along the southern coast of Maui in the desirable tourist area of Wailea. This beautifully appointed one-bedroom, two-bathroom condo accommodates up to four guests, making it ideal for families or groups...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Elua Village | 2005

Wailea Elua Village 2005 is a stunning two-bedroom, two-bathroom vacation rental located in the desirable Wailea region of Maui. This beautifully appointed condo offers a perfect blend of luxury and comfort.The spacious interior features an open-concept design that...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Ekolu Village | 1703

Wailea Ekolu 1703 is a stunning one-bedroom, two-bath ocean view vacation rental on the beautiful island of Maui that comfortably sleeps up to four guests. As you step into this spacious rental, you'll immediately be greeted by breathtaking views of the shimmering...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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