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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  • 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 $716 
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  • 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
    6  reviews
    from $575 
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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 $511 
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  • 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 $1,191 
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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
    50  reviews
    from $250 
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  • Wailea Elua Village 1301

    G O L D   R A T I N GDestination Residences 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 décor. ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Wailea
    1  reviews
    from $900 
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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
    67  reviews
    from $815 
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  • SEASPIRIT AT ANDAZ WAILEA RESIDENCES WELCOMES YOU! THE ULTIMATE LUXURY ESCAPE!

    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 $3,852 
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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
    50  reviews
    from $1,906 
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  • 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
    51  reviews
    from $432 
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  • Stunning Remodel, Fantastic Lower Village Location, 1 Minute to Pool & Beach! 6C

    Wailea Ekahi 6C is a stunning, spacious, fully renovated ground-floor one-bedroom/two-bathroom vacation condo in the prestigious Wailea resort district on the 'sunny side' of Maui. The unit has undergone a major high-end designer remodel, ...

    • 1 bedroom
    • 2 bathroom
    • Sleeps 3
    Hawaii> Wailea
    115  reviews
    from $435 
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  • WAILEA LUXURY IS YOURS!!! SOLARA LUXE POOL VILLA D101 at Wailea Beach Villas!

    Solara Luxe Plunge Pool Villa D101 at the exclusive Wailea Beach Villas is a ground level walk-in three bedroom, three and a half bath luxurious upscale private villa residence with nearly 3,300 square feet. Welcome to a sublime private retreat ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Wailea
    12  reviews
    from $3,309 
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  • WONDERFUL WAILEA IS OPEN! MODERN LUXURY & PANORAMIC OCEAN VIEWS AT BEAUTIFUL MODERN MAUI I404!

    Modern Maui I404, set on the 4th floor (out of 5) at the beachfront Wailea Beach Villas Resort on Maui Island, has joined our exquisite collection of exceptional villas managed exclusively by Private Paradise Villas. I404 was purchased by new ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    4  reviews
    from $1,777 
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  • TOP ROW CENTER-"GRAND WAILEA ACCESS" BEST VIEWS IN HO'OLEI

    TOP ROW CENTER-PANORAMIC OCEAN VIEWS-COMFORT & STYLE
    AND THE BEST LANAI IN HO'OLEI.
    INQUIRE FIRST BEFORE BOOKING REQUEST
    ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Wailea
    37  reviews
    from $3,995 
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  • SUMMER/FALL SPECIALS PRICING! MAKE MAUI MEMORIES OF A LIFETIME THIS SUMMER AT CASTAWAY COVE C201!

    C201 Castaway Cove Ocean View Villa has been recently decorated and upgraded to create an all-new living environment. The property owners have spared no expense in working with our team of professionals to create a uniquely elegant, comfortable ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Wailea
    9  reviews
    from $1,495 
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  • SUMMER SAVINGS! WAILEA'S MOST REQUESTED OCEAN FRONT LUXURY VILLA - ROYAL ILIMA A201!

    *An extensive redecoration is underway in A201 Royal Ilima. We are showing older photos still. If you reserve A201 Royal Ilima from late spring this year and beyond, you will be welcomed by many new improvements in the great room, patio, and ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Wailea
    9  reviews
    from $5,009 
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  • Wailea Ekahi Village 39A

    If it’s privacy you want, Wailea Ekahi Village 39A is tucked discreetly behind a row of towering tropical plants offering guests a private oasis to relax, entertain or enjoy a family barbecue.Tasteful décor and updated appliances inside ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Wailea
    1  reviews
    from $460 
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  • SOUTH MAUI WELCOMES YOU TO ENJOY TOP FLOOR OCEAN VIEWS AND TOP TIER LUXURY! SANDCASTLES SUITE L509

    *A fresh redecoration is just wrapping up for L509 Sandcastles Suite. We are showing older photos still. If you reserve L509 Sandcastles Suite from May 2023 onwards, you will be welcomed by some very nice improvements in most rooms, including a ...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Wailea
    8  reviews
    from $2,068 
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  • FALL SPECIAL PRICING! LUXURY & VIEWS AT AQUA LANI J305 WAILEA BEACH VILLAS!

    Aqua Lani J305 is a stunning, upscale Wailea Beach Villa. J305 was recently enhanced with the addition of a three-piece Natuzzi-brand Italian white leather sofa set to the great room, along with additional sofas and lounging/seating added to the...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Wailea
    11  reviews
    from $1,583 
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  • Makena Surf F208 - Oceanfront Platinum condo!

    P L A T I N U M   R A T I N GDestination Residences 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
    15  reviews
    from $1,025 
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  • CONTEMPORARY ELEGANCE AND OCEAN VIEWS At SOUTH MAUI'S SANDY SURF K508!

    Sandy Surf Villa K508, with over 3,300 square feet and 3 bedrooms, extra den alcove bedroom and 3 bathrooms, located on the top floor (5th) in a premiere panoramic ocean view setting, is one of the most spectacular private residences available ...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Wailea
    11  reviews
    from $1,395 
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  • LUXURY OCEANFRONT MAKENA SURF - 3 BR/3 BA - CONTACT OWNER FOR SPECIAL RATE

    Welcome to the newly renovated, top floor ''Turquoise Cove'' Villa - Makena Surf F301. This amazing property has unsurpassed ocean views, with a unique, double wrap-around lanai, perfect for enjoying tropical sunsets or catching the occasional ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Wailea
    45  reviews
    from $1,150 
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  • Wailea Elua Village 1303

    P L A T I N U M  R A T I N GDestination Residences Hawaii’s signature Platinum category rating is reserved for those residences that exemplify outstanding interior quality, comfort and design. Superior furnishings and unique fixtures and ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Wailea
    2  reviews
    from $1,159 
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  • Wailea Elua Village 708

    G O L D   R A T I N GDestination Residences 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 décor. ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    1  reviews
    from $685 
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  • Wailea Ekahi Village 10F

    G O L D   R A T I N GDestination Residences 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 décor. ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Wailea
    1  reviews
    from $375 
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  • STAY AND PLAY IN SOUTH MAUI AT THE FABULOUS FLORAL GARDENS POOL VILLA G102!

    Vacation here in sublime comfort in a private retreat with twice the space and conveniences of a hotel suite, including a full kitchen and in-villa grill and laundry room - at a fraction of the cost charged by corporate hotels or other villa ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Wailea
    10  reviews
    from $2,850 
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  • Wailea Elua Village 2006

    P L A T I N U M   R A T I N G
    Destination Residences 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
    6  reviews
    from $1,389 
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  • Makena Surf C207 - Oceanfront condo

    G O L D   R A T I N GDestination Residences 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 décor. ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    1  reviews
    from $1,233 
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  • Wailea Elua Village 2104

    P L A T I N U M  R A T I N GDestination Residences 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
    1  reviews
    from $655 
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  • Wailea Elua Village 2009

    G O L D   R A T I N GDestination Residences 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 décor. ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Wailea
    1  reviews
    from $711 
      View Property   Book Now