Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Narrow Results

Wailea: Condos, Studios & More (232)

  • 1 - 30 of 232
    • Studio
    • 1 BA
    • Sleeps 3
    10
    Request to Book View Details
    24 hrs Confirmation within 24 hours
      • 1 BR
      • 1 BA
      • Sleeps 5
      12
      Request to Book View Details
      24 hrs Confirmation within 24 hours
        • 1 BR
        • 1 BA
        • Sleeps 3
        27
        Request to Book View Details
        24 hrs Confirmation within 24 hours
          • 2 BR
          • 2 BA
          • Sleeps 6
          19
          Request to Book View Details
          24 hrs Confirmation within 24 hours
            • Studio
            • 1 BA
            • Sleeps 2
            Request to Book View Details
            24 hrs Confirmation within 24 hours
              • 2 BR
              • 2 BA
              • Sleeps 5
              16
              Request to Book View Details
              24 hrs Confirmation within 24 hours
                • 2 BR
                • 1 BA
                • Sleeps 4
                74
                Request to Book View Details
                24 hrs Confirmation within 24 hours
                  • 2 BR
                  • 2 BA
                  • Sleeps 6
                  13
                  Request to Book View Details
                  24 hrs Confirmation within 24 hours
                    • 2 BR
                    • 2 BA
                    • Sleeps 6
                    6
                    Request to Book View Details
                    24 hrs Confirmation within 24 hours
                      • 2 BR
                      • 2 BA
                      • Sleeps 6
                      14
                      Request to Book View Details
                      24 hrs Confirmation within 24 hours
                      Special Offer! >>>---------> $20 OFF SEPTEMBER OPEN DATES (while they last) April 24 - May 22
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        65
                        Request to Book View Details
                        24 hrs Confirmation within 24 hours
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          12
                          Request to Book View Details
                          24 hrs Confirmation within 24 hours
                            • 2 BR
                            • 2 BA
                            • Sleeps 6
                            8
                            Request to Book View Details
                            24 hrs Confirmation within 24 hours
                              • 2 BR
                              • 2 BA
                              • Sleeps 5
                              Request to Book View Details
                              24 hrs Confirmation within 24 hours
                                • 3 BR
                                • 3 BA
                                • Sleeps 6
                                4
                                Request to Book View Details
                                24 hrs Confirmation within 24 hours
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 5
                                  6
                                    • 1 BR
                                    • 2 BA
                                    • Sleeps 4
                                    9
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      22
                                        • 1 BR
                                        • 2 BA
                                        • Sleeps 4
                                        21
                                        Request to Book View Details
                                        24 hrs Confirmation within 24 hours
                                          • 1 BR
                                          • 2 BA
                                          • Sleeps 6
                                          6
                                          Request to Book View Details
                                          24 hrs Confirmation within 24 hours
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 6
                                            2 Reviews
                                            Request to Book View Details
                                            24 hrs Confirmation within 24 hours
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              10
                                              Request to Book View Details
                                              Instant Instant confirmation
                                                • 1 BR
                                                • 2 BA
                                                • Sleeps 4
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  48
                                                  Request to Book View Details
                                                  Instant Instant confirmation
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 4
                                                    7
                                                    Request to Book View Details
                                                    Instant Instant confirmation
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 7
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        50
                                                        Request to Book View Details
                                                        24 hrs Confirmation within 24 hours
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          1 Review
                                                          Request to Book View Details
                                                          24 hrs Confirmation within 24 hours
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 4
                                                            3
                                                            Request to Book View Details
                                                            24 hrs Confirmation within 24 hours
                                                            • 1 - 30 of 232
                                                             

                                                            Recent Wailea Reviews

                                                            Beautiful, Awesome and Charming

                                                            5 of 5
                                                            BEST.STAY.EVER. This gorgeous charming house was absolutely perfect. Very clean and it gives you a comfortable feeling of home. The beds were absolutely comfortable, and we were able to sleep with the windows open to allow the fresh air and breeze in. Stewart and Andrea provided a book with wonderful places to visit, and have the privacy you wanted. I would recommend this house to anyone wanting to visit Maui. Thank you Stewart and Andrea for a wonderful stay!
                                                            • Submitted: Apr 18, 2016
                                                            • Stayed: Apr 2016

                                                            Amazing Vacation!!

                                                            5 of 5
                                                            Bird of Paradise is truly Paradise! Right from the start we had amazing service when booking our reservation through Tropical Villa Vacations with excellent information provided on the 'little extra's' they offer to making sure everything was just what he wanted and by far exceeding any needs! We arrived late at night and the cottage was well lit, easy to find and Frankie had delicious fresh loaves and juice waiting for us...there was even music playing to greet us! Frankie and Dan spoiled us immensely and are the kindest people you will meet. The cottage is stocked with everything and more that we needed and the set up is perfect for families. They have added a fire pit on an additional deck just off the pool and after evening swims we enjoyed smores and sunsets by the fire. I can't say enough about this location but I do know we will return!
                                                            • Submitted: Jan 29, 2016
                                                            • Stayed: Jan 2016

                                                            Fantastic!

                                                            5 of 5
                                                            My husband and I celebrated our 25th wedding anniversary on this fantastic property. It was such a peaceful surrounding and a welcome change to the hustle and bustle of highly commercialized Kaanapali where we usually stay. The estate is located in close proximity to some fantastic dining including Mama's Fish House with the best seafood, atmosphere and location here on Maui. The views from the house were wonderful. Many shades of green painted the lush rain forest vegetation from every one of the windows,! While many of our days here on Maui were filled with our favorite excursions, we often chose to just stay at our new (but unfortunately temporary) home. I don't think I can count how many hours we spent on the beautiful private back lanai meditating to soothing water trickling from our private fountain, reading, having coffee/drinks/dinner, and just doing a whole lot of nothing. The superb staff was friendly, accommodating and filled with the “Aloha Sprit” that made an outstanding place to stay feel like home from the minute we arrived. We were sad to leave our new “discovery” and plan to always stay here in the future.
                                                            • Submitted: Nov 5, 2015
                                                            • Stayed: Oct 2015