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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
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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
    122  reviews
    from $383 
      View Property   Book Now

  • 5 Star Ocean View, Beach House Chic, Ask to see Video tour!

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

    ATTN: OUR COMPLEX IS REPLACING THE ROOF OF OUR BUILDING THE MONTH OF APRIL. PLEASE INQUIRE FOR SPECIAL APRIL RATE AND CONSTRUCTION INFORMATION.

    To view a cinematic video of the property and surrounding ...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    71  reviews
    from $338 
      View Property   Book Now

  • Beautiful Ocean Views! ... 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 $325 
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  • PREMIER PANORAMIC OCEAN VIEWS! WBV I503

    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 stunning top floor penthouse with PANORAMIC Ocean Views!! VIEWS VIEWS VIEWS!!This luxurious ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 7
    Hawaii> Wailea
    70  reviews
    from $1,407 
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  • Ground Floor 2 BDRM Condo - Wailea Elua #1503

    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 $842 
      View Property   Book Now

  • Stunningly Remodeled Ocean View Unit - Wailea Ekahi #22D

    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 $439 
      View Property   Book Now

  • 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
    131  reviews
    from $330 
      View Property   Book Now

  • 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
    36  reviews
    from $297 
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  • Beautiful Listing! Fully Renovated! STUNNING VIEWS!! Elua 2305

    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 Elua Village, a private, beachfront resort that spans ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    58  reviews
    from $866 
      View Property   Book Now

  • Super 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
    97  reviews
    from $355 
      View Property   Book Now

  • 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
    9  reviews
    from $535 
      View Property   Book Now

  • 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 $894 
      View Property   Book Now

  • 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 $585 
      View Property   Book Now

  • 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 $1,151 
      View Property   Book Now

  • 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 $746 
      View Property   Book Now

  • Great view - close to beach/pools! Fully remodeled! Sleeps 5! Building 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
    21  reviews
    from $393 
      View Property   Book Now

  • 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
    54  reviews
    from $295 
      View Property   Book Now

  • 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
    52  reviews
    from $385 
      View Property   Book Now

  • 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
    128  reviews
    from $1,157 
      View Property   Book Now

  • 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
    80  reviews
    from $660 
      View Property   Book Now

  • Wailea Elua Village 1301

    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 ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Wailea
    1  reviews
    from $602 
      View Property   Book Now

  • 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. ...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    108  reviews
    from $375 
      View Property   Book Now

  • Perfect Couple Retreat! Stylish Renovated Top Floor Ocean View Condo


    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 Views from this High...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 2
    Hawaii> Wailea
    92  reviews
    from $250 
      View Property   Book Now

  • Luxurious 2.5 Bedroom Paradise - Wailea Beach Villa

    Our home is a spacious 1980 square foot, 2 bedroom/2 bath Wailea Beach Villa with a den that functions as a third bedroom. Located directly above the upper pool with a spectacular garden and pool view, this spectacular unit offers a generous ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    121  reviews
    from $1,099 
      View Property   Book Now

  • 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
    67  reviews
    from $825 
      View Property   Book Now

  • ULTRA LUXURY SEASPIRIT 811 3 Br/4Ba RESIDENCE VILLA, HOT TUB SPA SLEEPS 8!

    SeaSpirit Villa 811 at Andaz Maui at Wailea Resort is a contemporary styled, privately-owned and independently-managed 3 bedroom, 4 bath ocean view second floor resort residence. SeaSpirit is set in a prime location within the resort just steps ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Wailea
    2  reviews
    from $2,384 
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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
    108  reviews
    from $395 
      View Property   Book Now

  • 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
    54  reviews
    from $1,349 
      View Property   Book Now

  • 4 BD, 3BA & Den 'WAILEA BEACHFRONT' OCEAN VIEWS 3892 s.f. CONTEMPORARY ELEGANT

    Beachfront: Panoramic Ocean & Outer Island Views, Penthouse K-208, 4 Full Bedrooms & 3 Full Baths; Total 3892 S.F. The Wailea Beach Villas Finest Upgrades with a Complete 2017 & 2018 Renovation. Contemporary, One of a Kind. Sleeps Comfortably up...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Wailea
    91  reviews
    from $1,595 
      View Property   Book Now

  • 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 ...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 2
    Hawaii> Wailea
    53  reviews
    from $398 
      View Property   Book Now

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