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 Vacation Rental - Ekahi 53D Fabulous Ocean View Newly Renovated 1BR/1BA — Property 194155

    Vacation Condo rental in Wailea area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, resort
    • accept credit card
    7th night free! July 20 to September 30
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1785 - $2450 per property per week

  2. 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
    You Save on New 4BR Villa-Fun Guaranteed
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $9975 - $22050 per property per week

  3. 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
    Special Offer!! $1500/night 6/16-9/15
    S P E C I A L    O F F E R
    Rates (shown in USD)

  4. Exclusive!! Oceanfront Wailea Beach Villa with Private Plunge Pool — Property 161729

    Vacation Villa rental in Wailea area
    • Villa
    • 3 bedrooms , sleeps 6
    • 3 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • accept credit card
    Special Offer!! $3250/night 6/15-9/15
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $21350 - $35000 per property per week

  5. Beautifully Remodeled! Wonderful Ocean & Fairway Views! 3 bedrooms!Very Private! — Property 192880

    Vacation Condo rental in Wailea area
    • Condo
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, resort
    • accept credit card
    Rates (shown in USD)
    $1925 - $2065 per property per week

  6. The Palms: Ocean Views, Spacious Elegance, 1BR/2BA Wailea — Property 165920

    Vacation Villa rental in Wailea area
    • Villa
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • beach, near the ocean
    • accept credit card
    Rates (shown in USD)
    $1470 - $1925 per property per week

  7. Luxurious Condo with Ocean View — Property 319210

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 4
    • 2 bathrooms
    Rates (shown in USD)

  8. Re-Modeled Tropical Unit, with Partial Ocean View, Steps from the Pool — Property 167604

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • near the ocean, resort
    • accept credit card
    Rates (shown in USD)
    $1575 - $1750 per property per week

  9. Beautiful, Quiet Wailea Condo Close to Ocean - $175 Summer Special! — Property 158632

    Vacation Condo rental in Wailea area
    • Condo
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • near the ocean
    • accept credit card
    Rates (shown in USD)
    $1225 - $1820 per property per week

  10. Wailea Condo Getaway — Property 161243

    Vacation Condo rental in Wailea area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, near the ocean
    • swimming pool
    Rates (shown in USD)

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