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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (47 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • 1 HF BA
    • Sleeps 4
    Cottage #3617930
    47
    Viewed 279 times in the last 48 hours
      Wonderful! 4.8/5
      (25 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 4
      Condo #481883vb
      25
      Viewed 71 times in the last 48 hours
        Wonderful! 4.8/5
        (14 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 2
        Condo #500715vb
        14
        Viewed 116 times in the last 48 hours
          Wonderful! 4.9/5
          (37 reviews)
          avg/night
          • 1 BR
          • 2 BA
          • Sleeps 4
          Condo #229577vb
          37
          Viewed 32 times in the last 48 hours
            Exceptional! 5.0/5
            (41 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 5
            House #502088vb
            41
            Viewed 138 times in the last 48 hours
              Wonderful! 4.8/5
              (11 reviews)
              avg/night
              • 1 BR
              • 2 BA
              • Sleeps 2
              Condo #4272970
              11
              Viewed 149 times in the last 48 hours
                Exceptional! 5.0/5
                (38 reviews)
                avg/night
                • 1 BR
                • 1 BA
                • Sleeps 4
                Cottage #92086vb
                38
                Viewed 104 times in the last 48 hours
                  avg/night
                  • 1 BR
                  • 2 BA
                  • Sleeps 4
                  Condo #927424vb
                  2
                  Viewed 69 times in the last 48 hours
                    Exceptional! 5.0/5
                    (7 reviews)
                    avg/night
                    • 1 BR
                    • 2 BA
                    • Sleeps 2
                    Condo #408268vb
                    7
                    Viewed 27 times in the last 48 hours
                      Wonderful! 4.8/5
                      (13 reviews)
                      avg/night
                      • 1 BR
                      • 2 BA
                      • Sleeps 2
                      Condo #471127vb
                      13
                      Viewed 17 times in the last 48 hours
                        Exceptional! 5.0/5
                        (11 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 6
                        Condo #471550vb
                        11
                        Viewed 89 times in the last 48 hours
                          Wonderful! 4.8/5
                          (10 reviews)
                          avg/night
                          • 1 BR
                          • 2 BA
                          • Sleeps 4
                          Condo #329306vb
                          10
                          Viewed 30 times in the last 48 hours
                            Wonderful! 4.9/5
                            (57 reviews)
                            avg/night
                            • Studio
                            • 1 BA
                            • Sleeps 2
                            Condo #33820vb
                            57
                            Viewed 101 times in the last 48 hours
                              Exceptional! 5.0/5
                              (41 reviews)
                              avg/night
                              • 1 BR
                              • 2 BA
                              • Sleeps 4
                              Apartment #424748vb
                              41
                              Viewed 86 times in the last 48 hours
                                Wonderful! 4.9/5
                                (112 reviews)
                                avg/night
                                • 1 BR
                                • 2 BA
                                • Sleeps 4
                                Condo #144744vb
                                112
                                Viewed 111 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (19 reviews)
                                  avg/night
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Condo #694469vb
                                  19
                                  Viewed 79 times in the last 48 hours
                                    Excellent! 4.6/5
                                    (30 reviews)
                                    avg/night
                                    • Studio
                                    • 1 BA
                                    • Sleeps 2
                                    Condo #491236vb
                                    30
                                    Viewed 62 times in the last 48 hours
                                      Excellent! 4.7/5
                                      (25 reviews)
                                      avg/night
                                      • Studio
                                      • 1 BA
                                      • Sleeps 3
                                      Studio #756478vb
                                      25
                                      Viewed 148 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (24 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 8
                                        Condo #742008vb
                                        24
                                        Viewed 142 times in the last 48 hours
                                          Excellent! 4.5/5
                                          (24 reviews)
                                          avg/night
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Condo #436300vb
                                          24
                                          Viewed 64 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (12 reviews)
                                            avg/night
                                            • 1 BR
                                            • 2 BA
                                            • Sleeps 4
                                            Condo #811955vb
                                            12
                                            Viewed 71 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (15 reviews)
                                              avg/night
                                              • 1 BR
                                              • 2 BA
                                              • Sleeps 2
                                              Condo #678888vb
                                              15
                                              Viewed 49 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (19 reviews)
                                                avg/night
                                                • 1 BR
                                                • 2 BA
                                                • Sleeps 3
                                                Condo #579376vb
                                                19
                                                Viewed 77 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (18 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 2 BA
                                                  • Sleeps 4
                                                  Condo #467442vb
                                                  18
                                                  Viewed 10 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (64 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 3
                                                    Condo #263305vb
                                                    64
                                                    Viewed 123 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (39 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      Condo #501619vb
                                                      39
                                                      Viewed 58 times in the last 48 hours
                                                        Excellent! 4.6/5
                                                        (5 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                        Condo #895649vb
                                                        5
                                                        Viewed 89 times in the last 48 hours
                                                          Excellent! 4.7/5
                                                          (18 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                          Condo #502643vb
                                                          18
                                                          Viewed 83 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (20 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 4
                                                            Condo #472565vb
                                                            20
                                                            Viewed 28 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (40 reviews)
                                                              avg/night
                                                              • Studio
                                                              • 1 BA
                                                              • Sleeps 2
                                                              Condo #28298vb
                                                              40
                                                              Viewed 78 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (11 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 3
                                                                Condo #4079566
                                                                11
                                                                Viewed 93 times in the last 48 hours
                                                                  Excellent! 4.7/5
                                                                  (20 reviews)
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Condo #51420vb
                                                                  20
                                                                  Viewed 135 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (40 reviews)
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 5
                                                                    Condo #293806vb
                                                                    40
                                                                    Viewed 34 times in the last 48 hours
                                                                      Wonderful! 4.8/5
                                                                      (28 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      House #3590022
                                                                      28
                                                                      Viewed 121 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (17 reviews)
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 2 BA
                                                                        • Sleeps 2
                                                                        Condo #695511vb
                                                                        17
                                                                        Viewed 41 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (20 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 2 BA
                                                                          • Sleeps 4
                                                                          Villa #132943vb
                                                                          20
                                                                          Viewed 7 times in the last 48 hours
                                                                            Excellent! 4.6/5
                                                                            (9 reviews)
                                                                            avg/night
                                                                            • 1 BR
                                                                            • 2 BA
                                                                            • Sleeps 4
                                                                            Condo #156620
                                                                            9
                                                                            Viewed 59 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (22 reviews)
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 2 BA
                                                                              • Sleeps 2
                                                                              Condo #568230vb
                                                                              22
                                                                              Viewed 18 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (39 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                Condo #71926vb
                                                                                39
                                                                                Viewed 88 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (26 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 2
                                                                                  Condo #504483vb
                                                                                  26
                                                                                  Viewed 21 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (29 reviews)
                                                                                    avg/night
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 3
                                                                                    Cottage #25005vb
                                                                                    29
                                                                                    Viewed 62 times in the last 48 hours
                                                                                      Excellent! 4.7/5
                                                                                      (21 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 4
                                                                                      Condo #615427vb
                                                                                      21
                                                                                      Viewed 53 times in the last 48 hours
                                                                                        Excellent! 4.6/5
                                                                                        (14 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Condo #774987vb
                                                                                        14
                                                                                        Viewed 82 times in the last 48 hours
                                                                                          Exceptional! 5.0/5
                                                                                          (10 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 4
                                                                                          Condo #38686vb
                                                                                          10
                                                                                          Viewed 18 times in the last 48 hours
                                                                                            Exceptional! 5.0/5
                                                                                            (34 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 5
                                                                                            Condo #184640vb
                                                                                            34
                                                                                            Viewed 90 times in the last 48 hours
                                                                                              Exceptional! 5.0/5
                                                                                              (34 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 4
                                                                                              Condo #68048vb
                                                                                              34
                                                                                              Viewed 66 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (24 reviews)
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 4
                                                                                                Condo #621837vb
                                                                                                24
                                                                                                Viewed 58 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (42 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 5
                                                                                                  Villa #504417vb
                                                                                                  42
                                                                                                  Viewed 41 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (60 reviews)
                                                                                                    avg/night
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 2
                                                                                                    Condo #58293vb
                                                                                                    60
                                                                                                    Viewed 45 times in the last 48 hours
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 4
                                                                                                      Condo #774563vb
                                                                                                      4
                                                                                                      Viewed 45 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Wailea: Vacation Rentals (2,926)

                                                                                                       

                                                                                                      Recent Wailea Reviews

                                                                                                      NIce Condo

                                                                                                      5 of 5
                                                                                                      Condo is as pictured. Clean, comfortable, smooth check in process. Owner is very easy to deal with. Short drive to beautiful beaches. Great value for the Wialea area!
                                                                                                      • Submitted: Jan 16, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      Spectacular Stay at Auntie Kali's Cottage

                                                                                                      5 of 5
                                                                                                      Absolutely gorgeous! We have travelled to Maui numerous times and this is by far the nicest property we have ever stayed in. My family and I spent 11 days in tropical paradise at this beautifully decorated, impeccably landscaped, home away from home. From the moment we walked in...to the moment we left, we were so impressed with this lovely cottage, all of its high end contents and of course the view and location. The very private yard has lush landscaping with an amazing view of the ocean, Molokini and country side. We absolutely loved everything about this cottage, the pool, hot tub, outdoor shower, bbq, Tiki bar and especially the owners adorable Boston Terriers - Willie K, Georgia & Olivia. Carrie and Jim go all out to make sure your stay is perfect...right down to the chocolates on your pillow! The reviews and photos couldn't be more accurate and are really as beautiful as they depict. I would be remiss, if I did not mention the best part of this property...its owners. Carrie, Jim, Gene and Jean are the most warm and welcoming folks you'll ever meet. We loved sharing our ranching and rodeo life with y'all, especially Grandma Jean! Thank you for making our Christmas so special and becoming our Maui friends! Can't wait to see you in December 2018 Tammy and Guy Shapka
                                                                                                      • Submitted: Jan 8, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      PICKIEST RENTER IN THE WORLD

                                                                                                      5 of 5
                                                                                                      I am here now and floored by how perfect this condo is for us. We also rent our vacation homes and my standards are insanely high. The place is far nicer than the photos, super clean, organized, and in a fab location. Everything you need is already provided. So well kept and a perfect getaway for a couple. Quiet (except the glorious birds) and a haven to get away from it all. I would not arrive late at night as we did as it is a bit tricky to find but once here, it is a breeze to find again. Very responsive owners and tons of information. Kudos!
                                                                                                      • Submitted: Dec 29, 2016
                                                                                                      • Stayed: Dec 2016