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:

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  • Hula On In to Beach House Chic Style, Ask to see Video tour!

    Tax ID:TA-118-085-8368-01

    To view a cinematic video of the property and surrounding area, please copy and paste the following in your web browser: https://youtu.be/p-IFXezdx7s?si=nIys8zIoeMzy40h4

    For those seeking a gorgeous ocean...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 5
    Hawaii> Wailea
    125  reviews
    from $383 
      View Property
  • 5 Star Ocean View, Beach House Chic, Ask to see Video tour!

    Tax ID:TA-118-085-8368-01

    To view a cinematic video of the property and surrounding area, please copy and paste the following in your web browser: https://youtu.be/78en85-1Pss?si=pdORMe2nm9-tktgI

    Aloha Maui vacation planners, ...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    75  reviews
    from $260 
      View Property
  • Incredible Ocean View! ... 5 Star Reviews ... 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
    71  reviews
    from $351 
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  • PREMIER PANORAMIC OCEAN VIEWS! WBV I503

    This property is hotel zoned, and not being affected by the recent proposed legislation.

    Voted #3 Resort in Hawaii by Conde Nast Reader’s Choice Awards 2019!Don't miss this amazing opportunity to book the vacation of your dreams in this...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 7
    Hawaii> Wailea
    71  reviews
    from $1,185 
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  • Nestled Near the Pool with Stunning Grounds -Wailea Elua 1503- Getaway & Relax!

    Highly cleaned and sanitized for your vacation. Ask about our AlohaSafeStay program.

    If you have a stay that qualifies for housekeeping services, traditional housekeeping service will be performed every 3rd day. This includes refreshing ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    1  reviews
    from $735 
      View Property
  • Tranquil Oceanview Corner Unit with Dual Lanais - Ekahi 22D - Soak Up the Sun!

    Highly cleaned and sanitized for your vacation. Ask about our AlohaSafeStay program.

    If you have a stay that qualifies for housekeeping services, traditional housekeeping service will be performed every 7th day. This includes refreshing...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    11  reviews
    from $339 
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  • nEnjoy the Amazing View and have a Mai Tai too!

    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
    134  reviews
    from $350 
      View Property
  • Prime Location! GC138!

    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 ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    37  reviews
    from $267 
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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
    58  reviews
    from $770 
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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
    101  reviews
    from $295 
      View Property
  • Wailea Ekahi Village 38F - Newly Renovated!

    Surrounded by tropical blooms, this spacious and uniquely laid out suite boasts fantastic ocean views.  Select a book from the extensive collection or enjoy an afternoon nap on one of the three separate lanais – one completely secluded in the...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    10  reviews
    from $396 
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  • Makena Surf B106 - Oceanfront Platinum condo!

    P L A T I N U M R A T I N GCoralTree Residence Collection Hawaii’s signature Platinum category rating is reserved for those residences that exemplify outstanding interior quality, comfort and design. Platinum residences reflect luxurious, ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    12  reviews
    from $747 
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  • Wailea Elua Village 1102 - Newly Renovated!

    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
    1  reviews
    from $465 
      View Property
  • Wailea Elua Village 1703

    ELUA 1703
    PLATINUM OCEAN FRONT CONDO WITH FULL PANORAMIC OCEAN VIEWS
    This ground level condo sleeps 6 with 2 bedrooms, 2 full baths, and a sleeper/sofa.
    Elua 1703 is a unique ocean front property. It is positioned directly in front ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    5  reviews
    from $1,041 
      View Property
  • Makena Surf E302 - Oceanfront condo

    G O L D   R A T I N GCoralTree Residence Collection Hawaii’s Gold category residences combine refined and stylish interiors with superior home conveniences. Each Gold residence maintains upgrades in interior design motifs and coordinated ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    13  reviews
    from $681 
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  • $200 SPRING SALE!Great view - close to beach! Fully remodeled!Sleeps 5! Bldg 30!

    This is a beautiful vacation condominium in the prestigious Wailea resort area regarded as the 'sunny side' of Maui!

    The Ekahi complex has just completed the construction of our brand new Pavilion at the beach and it is fabulous!! ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 5
    Hawaii> Wailea
    24  reviews
    from $350 
      View Property
  • 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
    56  reviews
    from $275 
      View Property
  • 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
    53  reviews
    from $402 
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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
    129  reviews
    from $987 
      View Property
  • 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
    85  reviews
    from $685 
      View Property