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Wailea(490)

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Closest to the Beach and Pool! LOCATION, LOCATION!! We own FIVE homes at Ho'olei
    3 Bedrooms,
  • 3 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 8
$650
per night

Closest to the Beach and Pool! LOCATION, LOCATION!! We own FIVE homes at Ho'olei

5 - 10 night Minimum Stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
  1. Maui >
  2. Wailea Townhome
#992677
    (17)
    Palms 904 Lanai overlook garden, Ocean & Mountains. Walk to Beach
      2 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    $243 - $250
    per night

    Palms 904 Lanai overlook garden, Ocean & Mountains. Walk to Beach

    5 - 7 night Minimum Stay
    • 2 BR,
    • 2 BA,
    • Sleeps 6
    1. Maui >
    2. Wailea Condo
    #351737
      (25)
      Wailea Home W/ Private Tennis Ct Steps from Keawakapu Bch
        3 Bedrooms, Sleeps 6
      $350 - $450
      per night

      Wailea Home W/ Private Tennis Ct Steps from Keawakapu Bch

      5 - 7 night Minimum Stay
      • 3 BR,
      • Sleeps 6
      1. Maui >
      2. Wailea House
      #283881
        (19)
        Renting a Vacation LIFESTYLE, not just a home
          3 Bedrooms,
        • 3 Bathrooms
          • , Sleeps 6
        $4,550 - $12,250
        per week

        Renting a Vacation LIFESTYLE, not just a home

        Book it Now!
        7 night Minimum Stay
        • 3 BR,
        • 3 BA,
        • Sleeps 6
        1. Maui >
        2. Wailea Townhome
        #325879
          (3)
          Fantastically Remodeled Condo with Huge Dynamic Ocean Views
            1 Bedrooms,
          • 2 Bathrooms
            • , Sleeps 4
          $260 - $280
          per night

          Fantastically Remodeled Condo with Huge Dynamic Ocean Views

          5 night Minimum Stay
          • 1 BR,
          • 2 BA,
          • Sleeps 4
          1. Maui >
          2. Wailea Condo
          #19514vb
            (14)
            'Wailea Surf' Villa at Wailea Beach Villas: Exquisite Island Style Villa!
              2 Bedrooms,
            • 2 Bathrooms
              • , Sleeps 6
            $645 - $1,395
            per night

            'Wailea Surf' Villa at Wailea Beach Villas: Exquisite Island Style Villa!

            3 - 7 night Minimum Stay
            • 2 BR,
            • 2 BA,
            • Sleeps 6
            1. Maui >
            2. Wailea Villa
            #275052
              (74)
              Wailea Beach Villa- Stunning Ocean Sunsets in Amazing 4BR - Owner Direct Savings
                4 Bedrooms,
              • 3 Bathrooms
                • , Sleeps 10
              $1,250 - $1,400
              per night

              Wailea Beach Villa- Stunning Ocean Sunsets in Amazing 4BR - Owner Direct Savings

              5 - 7 night Minimum Stay
              • 4 BR,
              • 3 BA,
              • Sleeps 10
              1. Maui >
              2. Wailea Villa
              #278106
                40 Reviews
                Panoramic Ocean Views! - Wailea Beach Villas - Luxury 3 Bed / 3 Bath
                  3 Bedrooms,
                • 3 Bathrooms
                  • , Sleeps 8
                $995 - $2,195
                per night

                Panoramic Ocean Views! - Wailea Beach Villas - Luxury 3 Bed / 3 Bath

                3 - 7 night Minimum Stay
                • 3 BR,
                • 3 BA,
                • Sleeps 8
                1. Maui >
                2. Wailea Villa
                #370688
                  (34)
                  Luxury Living with Sophistication at Hoolei! *****FIVE STAR REVIEWS!
                    3 Bedrooms,
                  • 3 Bathrooms, 
                  • 1 Half Bath
                    • , Sleeps 6
                  $650 - $850
                  per night

                  Luxury Living with Sophistication at Hoolei! *****FIVE STAR REVIEWS!

                  5 - 10 night Minimum Stay
                  • 3 BR,
                  • 3 BA,
                  • 1 HF BA,
                  • Sleeps 6
                  1. Maui >
                  2. Wailea Townhome
                  #272496
                    (12)
                    Special Offer JUNE SPECIALS!!! (May 25 - June 25)
                    Premium Ocean Hibiscus 23-1 (biggest) Fr $645
                      3 Bedrooms,
                    • 3 Bathrooms, 
                    • 1 Half Bath
                      • , Sleeps 8

                    Premium Ocean Hibiscus 23-1 (biggest) Fr $645

                    • 3 BR,
                    • 3 BA,
                    • 1 HF BA,
                    • Sleeps 8
                    1. Maui >
                    2. Wailea Townhome
                    #224781vb
                      (36)
                      Luxury 2BR, Ocean View, Owner Direct - Read Our Guest Reviews!
                        2 Bedrooms,
                      • 2 Bathrooms
                        • , Sleeps 5
                      $395 - $485
                      per night

                      Luxury 2BR, Ocean View, Owner Direct - Read Our Guest Reviews!

                      5 night Minimum Stay
                      • 2 BR,
                      • 2 BA,
                      • Sleeps 5
                      1. Maui >
                      2. Wailea Condo
                      #212306
                        (54)
                        First Class..Panoramic Unobstructed Ocean View..Best of Hoolei!
                          3 Bedrooms,
                        • 3 Bathrooms, 
                        • 1 Half Bath
                          • , Sleeps 8
                        $650 - $1,500
                        per night

                        First Class..Panoramic Unobstructed Ocean View..Best of Hoolei!

                        5 night Minimum Stay
                        • 3 BR,
                        • 3 BA,
                        • 1 HF BA,
                        • Sleeps 8
                        1. Maui >
                        2. Wailea Townhome
                        #348249
                          (45)
                          Wailea Beach Villas - Stunning 2.5 Bedroom Paradise - luxurious and private
                            2 Bedrooms,
                          • 2 Bathrooms
                            • , Sleeps 6

                          Wailea Beach Villas - Stunning 2.5 Bedroom Paradise - luxurious and private

                          • 2 BR,
                          • 2 BA,
                          • Sleeps 6
                          1. Maui >
                          2. Wailea Villa
                          #156411
                            (30)
                            Panoramic Ocean Views! - * See Specials! * - 3 Bed/3 Bath
                              3 Bedrooms, Sleeps 8

                            Panoramic Ocean Views! - * See Specials! * - 3 Bed/3 Bath

                            • 3 BR,
                            • Sleeps 8
                            1. Maui >
                            2. Wailea Villa
                            #342422vb
                              (34)
                              New Remodel, New Calif King Bed, Ocean/Mountain/Garden/ Views
                                1 Bedrooms,
                              • 2 Bathrooms
                                • , Sleeps 4
                              $183 - $285
                              per night

                              New Remodel, New Calif King Bed, Ocean/Mountain/Garden/ Views

                              5 night Minimum Stay
                              • 1 BR,
                              • 2 BA,
                              • Sleeps 4
                              1. Maui >
                              2. Wailea Condo
                              #212578
                                (20)
                                Stunning Ocean View Wailea Beach Villa-Book Maui Condo Direct & Save
                                  4 Bedrooms,
                                • 3 Bathrooms
                                  • , Sleeps 10
                                $995 - $1,400
                                per night

                                Stunning Ocean View Wailea Beach Villa-Book Maui Condo Direct & Save

                                5 - 7 night Minimum Stay
                                • 4 BR,
                                • 3 BA,
                                • Sleeps 10
                                1. Maui >
                                2. Wailea Villa
                                #164181
                                  (40)
                                  Wailea Beachfront! Ocean and Garden views, private location
                                    1 Bedrooms,
                                  • 1 Bathroom
                                    • , Sleeps 4

                                  Wailea Beachfront! Ocean and Garden views, private location

                                  • 1 BR,
                                  • 1 BA,
                                  • Sleeps 4
                                  1. Maui >
                                  2. Wailea Condo
                                  #325317vb
                                    (12)
                                    Top Floor ~ Best View at Wailea Beach Villas ~ Penthouse 502
                                      2 Bedrooms,
                                    • 2 Bathrooms
                                      • , Sleeps 6
                                    $875 - $1,163
                                    per night

                                    Top Floor ~ Best View at Wailea Beach Villas ~ Penthouse 502

                                    5 - 10 night Minimum Stay
                                    • 2 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                    1. Maui >
                                    2. Wailea Condo
                                    #329626
                                      (6)
                                      Wailea Beach Villa Rated Perfect by Trip Advisor - Best Values Year Round
                                        4 Bedrooms,
                                      • 3 Bathrooms
                                        • , Sleeps 10
                                      $995 - $1,550
                                      per night

                                      Wailea Beach Villa Rated Perfect by Trip Advisor - Best Values Year Round

                                      5 - 7 night Minimum Stay
                                      • 4 BR,
                                      • 3 BA,
                                      • Sleeps 10
                                      1. Maui >
                                      2. Wailea Villa
                                      #230622
                                        Owner Direct - Wailea Elua Oceanfront, Fully Renovated
                                          2 Bedrooms,
                                        • 2 Bathrooms
                                          • , Sleeps 6

                                        Owner Direct - Wailea Elua Oceanfront, Fully Renovated

                                        • 2 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                        1. Maui >
                                        2. Wailea Condo
                                        #298134
                                          (14)
                                          2 Bd/2 BA Wailea Condo with 180 degrees Superior Ocean View;
                                            2 Bedrooms, Sleeps 4
                                          $250 - $295
                                          per night

                                          2 Bd/2 BA Wailea Condo with 180 degrees Superior Ocean View;

                                          5 night Minimum Stay
                                          • 2 BR,
                                          • Sleeps 4
                                          1. Maui >
                                          2. Wailea Condo
                                          #242787
                                            (10)
                                            Absolutely Gorgeous, Affordable, Luxurious Spacious Condo
                                              2 Bedrooms, Sleeps 9

                                            Absolutely Gorgeous, Affordable, Luxurious Spacious Condo

                                            • 2 BR,
                                            • Sleeps 9
                                            1. Maui >
                                            2. Wailea Condo
                                            #204169vb
                                              (40)
                                              Ho'olei in Wailea - Always Providing Excellent Service and VALUE!
                                                3 Bedrooms,
                                              • 3 Bathrooms, 
                                              • 1 Half Bath
                                                • , Sleeps 10

                                              Ho'olei in Wailea - Always Providing Excellent Service and VALUE!

                                              • 3 BR,
                                              • 3 BA,
                                              • 1 HF BA,
                                              • Sleeps 10
                                              1. Maui >
                                              2. Wailea Villa
                                              #272495
                                                (13)
                                                Wailea - Luxury, Comfort and Beachfront Living at our Polo Beach Club #408
                                                  2 Bedrooms,
                                                • 2 Bathrooms
                                                  • , Sleeps 4
                                                $595
                                                per night

                                                Wailea - Luxury, Comfort and Beachfront Living at our Polo Beach Club #408

                                                3 - 14 night Minimum Stay
                                                • 2 BR,
                                                • 2 BA,
                                                • Sleeps 4
                                                1. Maui >
                                                2. Wailea Condo
                                                #934398
                                                  (6)
                                                  Lose Yourself In The View and Have a Mai Tai Too! Last Minute Specials
                                                    1 Bedrooms,
                                                  • 2 Bathrooms
                                                    • , Sleeps 4

                                                  Lose Yourself In The View and Have a Mai Tai Too! Last Minute Specials

                                                  • 1 BR,
                                                  • 2 BA,
                                                  • Sleeps 4
                                                  1. Maui >
                                                  2. Wailea Condo
                                                  #456792vb
                                                    (4)
                                                    YOUR MAUI ESCAPE GET AWAY
                                                      1 Bedrooms,
                                                    • 2 Bathrooms
                                                      • , Sleeps 4
                                                    $330
                                                    per night

                                                    YOUR MAUI ESCAPE GET AWAY

                                                    5 - 7 night Minimum Stay
                                                    • 1 BR,
                                                    • 2 BA,
                                                    • Sleeps 4
                                                    1. Maui >
                                                    2. Wailea Condo
                                                    #444410vb
                                                      1 Review
                                                      Wow! Love this View!
                                                        2 Bedrooms,
                                                      • 2 Bathrooms
                                                        • , Sleeps 4

                                                      Wow! Love this View!

                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 4
                                                      1. Maui >
                                                      2. Wailea Condo
                                                      #447005vb
                                                        Ocean View, Remodeled, Stuff for Kids, Clean
                                                          2 Bedrooms, Sleeps 6
                                                        $250 - $275
                                                        per night

                                                        Ocean View, Remodeled, Stuff for Kids, Clean

                                                        4 - 7 night Minimum Stay
                                                        • 2 BR,
                                                        • Sleeps 6
                                                        1. Maui >
                                                        2. Wailea Condo
                                                        #236229
                                                          (26)
                                                          Wailea - Luxury, Comfort and Beachfront Living at Polo Beach Club #408
                                                            2 Bedrooms,
                                                          • 2 Bathrooms
                                                            • , Sleeps 4
                                                          $595
                                                          per night

                                                          Wailea - Luxury, Comfort and Beachfront Living at Polo Beach Club #408

                                                          2 - 14 night Minimum Stay
                                                          • 2 BR,
                                                          • 2 BA,
                                                          • Sleeps 4
                                                          1. Maui >
                                                          2. Wailea Condo
                                                          #71367vb
                                                            (6)
                                                            Panoramic Ocean Views on Greenbelt
                                                              1 Bedrooms,
                                                            • 2 Bathrooms
                                                              • , Sleeps 4
                                                            $225 - $400
                                                            per night

                                                            Panoramic Ocean Views on Greenbelt

                                                            2 night Minimum Stay
                                                            • 1 BR,
                                                            • 2 BA,
                                                            • Sleeps 4
                                                            1. Maui >
                                                            2. Wailea Condo
                                                            #457082vb
                                                              2 Reviews
                                                              • 1 - 30 of 490
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