Wailea Vacation Rentals

Wailea is a luxurious resort community located in the base of Mt. Haleakala on the south shore of the island. Here you will find several great white-sand beaches, including Wailea Beach, which was named "America's Best Beach" by Dr. Beach in 1999. Wailea is also one of the world's best golf destinations featuring three championship golf courses with breathtaking ocean views from every hole. So if you like to play golf, you will find Wailea a true paradise. There is a large selection of vacation rentals in Wailea, everything from condos to upscale villas. So start planning your Maui vacation today and find your perfect Wailea vacation rental below.

Browse Wailea Vacation Rentals by condo/hotel name:

Ekahi Village
Elua Village
Wailea Grand Champions
Hoolei
Mana Kai
Polo Beach Club
Wailea Ekolu
The Palms at Wailea
Wailea Ekahi
Wailea Beach Villas
Wailea Point

  • Beautiful Ocean View! ... 5 Star Hospitality! Hoʻokipa at Wailea Ekolu Village.

    ALOHA!

    Welcome to Our Maui Condo! Hoʻokipa means "hospitality"! You're sure to enjoy our Wailea Ekolu home and the Maui sunsets with SPECTACULAR OCEAN VIEWS of Molokini and the neighboring island of Kahoolawe.

    Our condo is ...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    from $477 
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  • 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 ...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    from $578 
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  • Book 6 nights and get the 7th free!Top Floor!GC 138

    Special Promotion: Book 6 nights and get the 7th free!

    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 ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    from $580 
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  • Beautiful Listing! Fully Renovated! STUNNING VIEWS!! 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 ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    from $1,237 
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  • Amazing Ocean Views! 5 Star Reviews! ʻIke Kai at Wailea Ekolu Village

    Aloha!

    Welcome to our Our Maui Condo! ʻIKE KAI means "OCEAN VIEWS". This wonderful one bedroom, two bath, ground floor condo with BEAUTIFUL OCEAN VIEWS will satisfy even the most discriminating visitor.

    Our condo is located on ...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    from $509 
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  • Wailea Ekahi Village | 38F

    Nestled in the heart of Wailea, Wailea Ekahi 38F is an exquisite vacation rental that offers a luxurious and serene Maui escape. This stunning two-bedroom, two-bathroom condo takes full advantage of its second floor positioning and boasts ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    from $932 
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  • Makena Surf | B106 | Beachfront Resort

    Welcome to Makena Surf B106, a stunning two-bedroom beachfront suite just steps away from the golden sands and the ocean's edge. This beautifully appointed residence combines luxury and comfort, featuring elegant tray ceilings, exquisite wood ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    from $951 
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  • Wailea Beach Villas | PH406

    Wailea Beach Villas Penthouse 406 is desirable for its remarkable Pacific Ocean and Island views. This upscale penthouse vacation rental features two bedrooms, two bathrooms, exotic hardwood furnishings, an incredible antiquities collection, and...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    from $1,458 
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  • Wailea Elua Village | 1102

    This ocean view one-bedroom Wailea Elua Village condo is a great home base for experiencing the joys and beauty of south Maui. Easily walk down to the white-sand Ulua Beach that fronts this property. Be one of the first in the ocean in the ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Wailea
    from $674 
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  • Wailea Elua Village | 1703

    Elua 1703 is a distinctive oceanfront vacation rental, perfectly situated directly in front of the renowned Ulua Beach and the Wailea Beachfront Walking Path. What sets it apart is its unique privacy, surrounded on three sides by lush, ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    from $1,752 
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  • 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 ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Wailea
    from $2,380 
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  • Enjoy Beautiful Sunsets with this Ocean View!!

    NOTICE: OUR COMPLEX WILL BEGIN ROOF REPLACEMENT ON ALL BUILDINGS BEGINNING MAY 1, 2023. (Our building is scheduled Oct. 27 - Nov. 13). There could be outside construction noise throughout the complex during this time.

    This beautiful ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    from $329 
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  • FULL OCEAN VIEW WAILEA

    Full renovation of this condo was completed December 2020. Both bathrooms, master bedroom, as well as entire condo painted and replacement of baseboards and door trims throughout.

    Bright airy updated large 1 bedroom 2 bath top floor in ...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 3
    Hawaii> Wailea
    from $590 
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  • Ocean View, Close to Beach&Pool Sleeps 10

    Experience the luxury of a resort community while staying in a home larger than four hotel rooms!! Beach and Snow Rentals offers this spacious 3 bedroom, 3.5 bath two story townhome featuring a private elevator, finely appointed interior, and ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Wailea
    from $1,436 
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  • Modern Spacious Beachfront Luxury in Wailea. Family Friendly!

    A modern 2 bedroom, 2 bath condo w. extra bunk beds and an amazing ocean view!

    South Maui is one of the most beautiful destinations in all of Maui and Wailea Ekahi Village is the perfectly-situated, beachside resort we call home . Guests...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    from $1,137 
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  • Summer Special! Perfect Couple Retreat! Stylish Renovated Top Floor Ocean View


    Summer Special! Perfect Couple Retreat! Enjoy Sweeping Ocean Views High End Top Floor Remodel

    TOP FLR OCEAN VIEW BEAUTIFUL REMODEL, ENHANCED CLEANING

    https://www.youtube.com/watch?v=Or2Innjn2LE

    Enjoy Sweeping Ocean ...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 2
    Hawaii> Wailea
    from $256 
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  • Luxurious 2.5 Bedroom Paradise - Wailea Beach Villa

    IMPORTANT NOTICE: Lower Lobby / Resort Lanai Tile Project - Late August through October, 2024

    A tile project on the lower lobby / resort lanai will be taking place from late August through the end of October 2024. The work will occur ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    from $1,492 
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  • 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...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 5
    Hawaii> Wailea
    from $1,099 
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  • Panoramic Ocean View In The Heart Of Wailea On Golf Course

    Enjoy spectacular panoramic ocean views from this beautiful condo in a truly private setting! This is one of the best located units in the complex providing unobstructed ocean views from the living area, dining area, kitchen, master bedroom and...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 5
    Hawaii> Wailea
    from $575 
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  • Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third Tier

    Located on the third tier on the south side of the Ho’olei Resort on Maui, our two-level villa has jaw-dropping Pacific Ocean views and is perfectly perched to capture the crystal blue sky during the day and breathtaking sunsets in the ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 7
    Hawaii> Wailea
    from $1,390 
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