Wailea Hawaii Vacation Rentals and Vacation Homes

 90 Rentals in Wailea

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Property 85267

Wailea Diamond Estate

  • The modern and spacious Wailea Diamond estate provides luxury and privacy, yet easy access to the ocean.
  • House in Wailea (Near Kihei)
  • 7 Bedroom(s), Sleeps 14
  • 5 Bathroom(s)
Property 85384

Sunset Pavillion

  • Welcome to Sunset Pavilion, one of Luxurious Destination’s newest exclusive vacation homes.
  • House in Makena (Near Wailea)
  • 4 Bedroom(s), Sleeps 10
  • 3 Bathroom(s)
Property 85389

Wailea Sapphire Estate

  • Here is a beautifully updated, four bedroom, private, gated estate that is just steps away from “Keawakapu Beach”,
  • House in Wailea
  • 4 Bedroom(s), Sleeps 10
  • 4 Bathroom(s)
Property 85370

Kamaole Villa

  • A stay at Kama'ole Villa is sure to create cherished long-lasting memories of the beauty of Maui.
  • House in Wailea (Near Kihei)
  • 3 Bedroom(s), Sleeps 6
  • 3 Bathroom(s)
Property 85403

Hoolei

  • If you are looking for the privacy of a vacation home but still want the amenities of a resort, Ho'olei is perfect. All that is missing is you!
  • House in Wailea
  • 3 Bedroom(s), Sleeps 8
  • 3 Bathroom(s)
Property 85445

South Maui Beach House

  • From the beautiful "South Maui Beach House" at Makena Landing in South Maui, you can experience all of it!
  • House in Makena (Near Wailea)
  • 3 Bedroom(s), Sleeps 6
  • 3 Bathroom(s)
Property 112063

Ho'olei #93-5 Spectacular

  • Ho'olei #93-5 Spectacular Home Directly Over the Waterfall Pool !
  • Condo in Wailea (Near Wailea Beach)
  • 3 Bedroom(s), Sleeps 8
  • 2 Bathroom(s)
Property 112077

Palms at Wailea #2002

  • Palms at Wailea #2002
  • Condo in Wailea
  • 3 Bedroom(s), Sleeps 8
  • Weekly Rates from $2,275 - $2,975
Property 112081

Wailea Beach Villa I-203

  • Wailea Beach Villa I-203
  • Condo in Wailea (Near Wailea Beach)
  • 3 Bedroom(s), Sleeps 6
  • Weekly Rates from $5,565 - $6,300
Property 112089

Ho'olei #T6 - Biggest Flo

  • Ho'olei #T6 - Biggest Floor Plan. Close to Wailea Beach - Great 2013 Rates !
  • Condo in Wailea (Near Wailea Beach)
  • 3 Bedroom(s), Sleeps 8
Property 112091

Ho'olei #S3 - Easy Access

  • Ho'olei #S3 - Easy Access to Beach and Pool !
  • Condo in Wailea
  • 3 Bedroom(s), Sleeps 6
  • 2 Bathroom(s)
Property 112092

Ho'olei #39-3 'Ocean

  • 'Ocean's Invitation' Premier Location and View !
  • Condo in Wailea (Near Wailea Beach)
  • 3 Bedroom(s), Sleeps 8
  • 2.5 Bathroom(s)
Property 112103

Ho'olei #55-2 Luxurious N

  • Luxurious New Wailea Rental Home
  • Condo in Wailea (Near Wailea Beach)
  • 3 Bedroom(s), Sleeps 8
  • 2.5 Bathroom(s)
Property 112221

Wailea Elua 1305

  • Wailea Elua 1305
  • Condo in Wailea
  • 3 Bedroom(s), Sleeps 8
Property 85469

South Maui Sunset

  • "South Maui Sunset" is a perfect oceanfront vacation cottage located on a the south shores of Maui.
  • Cottage in Wailea
  • 2 Bedroom(s), Sleeps 6
  • 1 Bathroom(s)
Property 85483

Wailea Point

  • Wailea Point is an exclusive oceanfront community. Each luxury villa in Wailea Point is privately owned.
  • Villa in Wailea (Near Makena)
  • 2 Bedroom(s), Sleeps 4
  • 2 Bathroom(s)
Property 111758

Grand Champions #36

  • Grand Champions #36
  • Condo in Wailea
  • 2 Bedroom(s), Sleeps 6
  • Weekly Rates from $1,365 - $1,575
  • Wailea Ekolu #908 - Top Floor Two Bedroom with Big Ocean Views
  • Condo in Wailea
  • 2 Bedroom(s), Sleeps 4
  • Weekly Rates from $2,135 - $2,415
Property 111861

Palms at Wailea #1901

  • Palms at Wailea #1901
  • Condo in Wailea
  • 2 Bedroom(s), Sleeps 6
  • Weekly Rates from $1,400 - $1,925
Property 111864

Rainbow Deluxe

  • Rainbow Deluxe
  • Condo in Wailea
  • 2 Bedroom(s), Sleeps 4
  • Just minutes away the Shops at Wailea, fabulous, famous restaurants, and exceptional beaches add to your vacation experience.
  • Condo in Wailea (Near Wailea Beach)
  • 2 Bedroom(s), Sleeps 6
  • 2 Bathroom(s)
  • Weekly Rates from $1,750 - $1,995
  • The property features 2 pools, 2 Jacuzzi's, barbecues, and minutes from the Shops at Wailea, Wailea Beaches, fine and casual dining, Luaus
  • Condo in Wailea (Near Wailea Beach)
  • 2 Bedroom(s), Sleeps 4
  • 2 Bathroom(s)
  • Weekly Rates from $1,750 - $1,995
  • Grand Champions #49 - Ground Floor, Corner Location with Easy Pool Access !
  • Condo in Wailea (Near Wailea Beach)
  • 2 Bedroom(s), Sleeps 4
  • 2 Bathroom(s)
  • Weekly Rates from $1,750 - $1,995
Property 111905

Wailea Ekolu #1610

  • Wailea Ekolu #1610
  • Condo in Wailea
  • 2 Bedroom(s), Sleeps 5
  • Weekly Rates from $2,275 - $2,555
  • Wailea Ekahi #48A - Elegant Wailea Townhome with Ocean Views.
  • Condo in Wailea
  • 2 Bedroom(s), Sleeps 4
  • Weekly Rates from $3,185 - $3,780


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