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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.

  1. Wailea Elua Village #701 - Luxury 2-Bedroom with Ocean View & Perfect Location. — Property 212306

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 5
    • 2 bathrooms
    • beach, near the ocean
    • pool
    $50/night discounts for Nov & Dec 2009!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2450 - $3150 per property per week
  2. Grand Champions #42
    Ocean View, Remodeled, Stuff for the Kids, Early booking discounts-low season! — Property 236229

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • tennis court
    Rates (shown in USD)
    $1750 - $2065 per property per week
  3. Enjoy Dinner and Wine on the Beach for a Maui Sunset Treat! — Property 188896

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, village
    • tennis court
    Rates (shown in USD)
    $2555 - $2765 per property per week
  4. Wailea Maui Condo with Fabulous Ocean View — Property 242787

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • near the ocean, resort
    • pool
    Rates (shown in USD)
    $1575 - $2065 per property per week
  5. Grand Champions Villas #32
    Grand Champions, Remodeled, Ocean Views, Thanksgiving Special $225/nt — Property 186208

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 5
    • 2 bathrooms
    • beach, near the ocean
    • pool
    Rates (shown in USD)
    $1393 - $1960 per property per week
  6. Magnificent Panoramic Views!! Luxury Private Corner End Unit!! — Property 229269

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • balcony
    • air-conditioning
    Rates (shown in USD)
  7. Paradise at Wailea
    November Special!-$179 a night INCLUDING Thanksgiving — Property 167604

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • near the ocean, resort
    • pool
    Rates (shown in USD)
    $1575 - $1750 per property per week
  8. The Palms At Wailea
    The Palms- $150/nt for Remaining Dates in 2009!! — Property 163145

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • pool
    Rates (shown in USD)
    $1365 - $2450 per property per week
  9. Great Wailea Family Vacation Condo — Property 188978

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • near the ocean, resort
    • pool
    Rates (shown in USD)
    $1890 - $2030 per property per week
  10. Wailea Ekahi Village: 51D Stunning Ocean view — Property 7023747

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • adventure
    • air-conditioning
    Rates (shown in USD)
    $2625 - $3325 per condo per week

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