Search for vacation rental homes in Wailea

Beautiful Beaches are Only the Beginning in Wailea


With an unbeatable location on Maui’s sunny southern shore, Wailea invites you to leave all your worries behind on a getaway filled with white sand beaches, countless water sports, and scenic beauty that is beyond compare.


Once you step foot onto the land that is Wailea, it is easy to see how this place can truly be called paradise. One magnificent beach after another beckons with opportunities for swimming, snorkeling, scuba diving and even kayaking; all you need to do is heed the call and let every last ounce of stress fall by the wayside.


So where should you begin? Any of the beautiful beaches are certainly a treat, but Wailea Beach is the best place to get your feet wet with its spectacular swimming conditions, breathtaking views of Kahoolawe and Lanai, and gentle boogie boarding possibilities. And see that little crescent out in the distance? That is Molokini Crater, where you will be snorkeling or scuba diving in crystal clear water surrounded by schools of colorful fish.


However, if your Wailea vacation rental lies along a different stretch of sand, you can’t be too disappointed because the other options can certainly hold their own. The long golden sands of Mokapu Beach and Ulua Beach can satisfy your need for adventure with amazing snorkeling and swimming in calm water and spectacular bodysurfing when the waves kick up, while Polo Beach is a great place to simply relax, swim or snorkel to your heart’s content.


Although the beaches are certainly the centerpiece of Wailea, this area is more than just a one attraction wonder. If you are looking for other ways to fill up your stay in paradise, the three courses at the Wailea Golf Club, the renowned tennis of the Wailea Tennis Club, the one-of-a-kind treasures at The Shops at Wailea, and the natural beauty of La Perouse Bay are all waiting to make your Maui vacation everything you always imagined and more.

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  1. Wailea Beach Villa, Luxury w/Beautiful Ocean Views — Property 141228

    Vacation Villa rental in Wailea area
    • Villa
    • 3 bedrooms , sleeps 6
    • 3 bathrooms
    • beach, resort
    • accept credit card
    Holiday special $400 off nightly rate
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $7700 - $15400 per property per week

  2. Architect's Own Custom Estate in South Maui — Property 159525

    Vacation House rental in Wailea area
    • House
    • 4 bedrooms , sleeps 8
    • 3 bathrooms
    • 1 half bathroom
    • near the ocean, resort
    • accept credit card
    !!!! Thanksgiving Special !!!! $750/nite
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $8750 per property per week

  3. Exquisite 'Aloha Kai Suite' 3BD/3BA! Wailea Beach Villa by Owner Direct! — Property 163269

    Vacation Villa rental in Wailea area
    • Villa
    • 3 bedrooms , sleeps 8
    • 3 bathrooms
    • beach, resort
    • accept credit card
    25% OFF - Aloha Kai Suite Winter Special
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $6965 - $15365 per property per week

  4. Wailea Beach Villa w/Baby Grand- Breathtaking View & Luxurious Furnishings — Property 164181

    Vacation Villa rental in Wailea area
    • Villa
    • 4 bedrooms , sleeps 9
    • 3 bathrooms
    • beach, waterfront
    • accept credit card
    Guaranteed Best Deal Wailea Beach Villa
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $9975 - $22050 per property per week

  5. Serenity at the Wailea Oasis — Property 161624

    Vacation Villa rental in Wailea area
    • Villa
    • 3 bedrooms , sleeps 8
    • 3 bathrooms
    • beach, resort
    • accept credit card
    Christmas/New Years Still Available!!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $12250 - $17500 per property per week

  6. Upgrade to a Great Deal for Dazzling Aloha Contemporary Suite — Property 213130

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • accept credit card
    Rates (shown in USD)

  7. Polo Beach Club Wailea - Prime Beach Front Unit — Property 200492

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)

  8. Wailea Sunset Estate. Luxury Beachfront avail over Christmas — Property 147064

    Vacation Estate rental in Wailea area
    • Estate
    • 3 bedrooms , sleeps 9
    • 5 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
    $12950 - $21000 per property per week

  9. Ocean Pearl Luxury Wailea Beach Villa — Property 148475

    Vacation Villa rental in Wailea area
    • Villa
    • 3 bedrooms , sleeps 6
    • 3 bathrooms
    • 1 half bathroom
    • beach, resort
    • accept credit card
    Rates (shown in USD)
    $8400 - $11550 per property per week

  10. Winter Special avail over Xmas! Beach Breezes H201 3BR Luxury Ocean View — Property 162782

    Vacation Villa rental in Wailea area
    • Villa
    • 3 bedrooms , sleeps 6
    • 3 bathrooms
    • beach, resort
    • accept credit card
    Rates (shown in USD)
    $8400 - $17500 per property per week

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