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Wailea Chalets or Houses(18)

18 Results
5 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
    (16)
    $99 - $260
    per night
    2 - 3 night minimum stay
    • 1 BR,
    • 1 BA,
    • 1 HF BA,
    • Sleeps 4
      (8)
      5 - 7 night minimum stay
      • 4 BR,
      • 5 BA,
      • 1 HF BA,
      • Sleeps 10
        1 Review
        Book it Now!
        • 3 BR,
        • 3 BA,
        • Sleeps 6
          (3)
          Book it Now!
          3 night minimum stay
          • 2 BR,
          • 2 BA,
          • Sleeps 5
            (5)
            $1,350 - $1,600
            per night
            5 - 7 night minimum stay
            • 4 BR,
            • 3 BA,
            • 1 HF BA,
            • Sleeps 10
              (28)
              7 night minimum stay
              • 3 BR,
              • 2 BA,
              • 1 HF BA,
              • Sleeps 6
                (7)
                5 - 10 night minimum stay
                • 3 BR,
                • 2 BA,
                • Sleeps 6
                  7 night minimum stay
                  • 4 BR,
                  • 3 BA,
                  • 1 HF BA,
                  • Sleeps 10
                    (15)
                    5 night minimum stay
                    • 1 BR,
                    • 2 BA,
                    • Sleeps 4
                      7 - 14 night minimum stay
                      • 4 BR,
                      • 3 BA,
                      • Sleeps 8
                        (11)
                        5 night minimum stay
                        • 2 BR,
                        • 2 BA,
                        • Sleeps 4
                          Book it Now!
                          2 - 3 night minimum stay
                          • 4 BR,
                          • 2 BA,
                          • Sleeps 8
                            (25)
                            5 - 10 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 6
                              (7)
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 6
                                14 night minimum stay
                                • 4 BR,
                                • 3 BA,
                                • Sleeps 13
                                  • 2 BR,
                                  • Sleeps 4
                                    (7)
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                                    Recent Wailea Reviews

                                    Beautiful Wailea home in the perfect location.

                                    5 of 5
                                    My family had a wonderful week in this beautiful Ho'olei home in Wailea. It is a beautiful home and the perfect location. We enjoyed the beaches, walking path, pool and the local restaurants were all good. We have already recommended it to a few friends. Our granddaughter really enjoyed the pool and sand toys. Everyone loved the view and we were all up early every morning to enjoy the sunrise and of course mai tai's on the lanai watching the sunset! Thank you for greeting us upon our arrival and making your property so welcoming. BRH
                                    • Submitted: Aug 21, 2014
                                    • Stayed: Aug 2014

                                    AND THE BEAT GOES ON!

                                    5 of 5
                                    Another 5 Star Review for this amazing place! My family of four stayed here for a week. It is centrally located perfectly in South Maui The family caretakers Phil and Sharon live right on the property behind the house. You will hardly ever know that they are there until you need something. Genuinely nice people. Plenty of room, perfect layout for privacy, great grill cooking area, nice pool and located on edge of ranch property to give you that solitude. We stayed in Hawaii 1 1/2 months and this was one of the nicest places and locations that we stayed.
                                    • Submitted: Aug 14, 2014
                                    • Stayed: Aug 2014

                                    Paradise

                                    5 of 5
                                    How do you describe paradise?? If there were enough words to describe paradise they would apply to this property. We are a family 5 which included a 16 month old. The house was perfect for our family. The little guy had plenty of room to run back and forth through the living area and he thought the spa was his own private pool. We all loved having our own pool and it was always clean and inviting. We all appreciated the privacy and quietness of this property. The views from the upper deck were amazing! All the amenities that one would need were on the property. We have stayed at condos on other vacations but this house is the best by far! The owner was more than accommodating and was always available to answer our questions. My family and I hope to return to this property in the near future. It was the BEST vacation ever!
                                    • Submitted: Jul 17, 2014
                                    • Stayed: Jul 2014