Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartment
Condo
Cottage
House
Studio
Townhome
Villa
Barn
Boat
Bungalow
Cabin
Castle
Chalet
Estate
Farmhouse
Hotel
Lodge
Yacht

Location Type

Even More Filters

Features

Managed By

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

Wailea Vacation Rentals with Online Payment(438)

438 Results
Book it Now!
5 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
    1 Review
    Book it Now!
    1 - 14 night minimum stay
    • 2 BR,
    • 2 BA,
    • Sleeps 6
      (5)
      4 - 14 night minimum stay
      • 2 BR,
      • 2 BA,
      • Sleeps 4
        (18)
        5 night minimum stay
        • 1 BR,
        • 2 BA,
        • Sleeps 4
          (20)
          Book it Now!
          6 - 10 night minimum stay
          • 3 BR,
          • 3 BA,
          • 1 HF BA,
          • Sleeps 8
            (13)
            Book it Now!
            3 night minimum stay
            • 2 BR,
            • 2 BA,
            • Sleeps 8
              (4)
              Book it Now!
              3 - 7 night minimum stay
              • 1 BR,
              • 2 BA,
              • Sleeps 4
                (27)
                Book it Now!
                6 - 8 night minimum stay
                • 2 BR,
                • 2 BA,
                • Sleeps 6
                  (4)
                  Book it Now!
                  6 - 10 night minimum stay
                  • 3 BR,
                  • 3 BA,
                  • 1 HF BA,
                  • Sleeps 6
                    (7)
                    Book it Now!
                    3 - 14 night minimum stay
                    • 1 BR,
                    • 2 BA,
                    • Sleeps 5
                      2 Reviews
                      $650 - $1,950
                      per night
                      Book it Now!
                      6 - 10 night minimum stay
                      • 3 BR,
                      • 3 BA,
                      • 1 HF BA,
                      • Sleeps 6
                        2 Reviews
                        Book it Now!
                        3 - 7 night minimum stay
                        • 2 BR,
                        • 2 BA,
                        • Sleeps 5
                          (4)
                          $1,595 - $5,000
                          per night
                          Book it Now!
                          5 - 14 night minimum stay
                          • 3 BR,
                          • 4 BA,
                          • Sleeps 6
                            (3)
                            5 - 10 night minimum stay
                            • 2 BR,
                            • 2 BA,
                            • Sleeps 6
                              (7)
                              Book it Now!
                              6 - 7 night minimum stay
                              • 1 BR,
                              • 2 BA,
                              • Sleeps 4
                                (3)
                                5 night minimum stay
                                • 3 BR,
                                • 3 BA,
                                • 1 HF BA,
                                • Sleeps 8
                                  (25)
                                  Book it Now!
                                  6 - 7 night minimum stay
                                  • 2 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                    2 Reviews
                                    Book it Now!
                                    3 - 5 night minimum stay
                                    • 1 BR,
                                    • 2 BA,
                                    • Sleeps 2
                                      (3)
                                      Book it Now!
                                      1 - 7 night minimum stay
                                      • 2 BR,
                                      • 2 BA,
                                      • Sleeps 6
                                        Book it Now!
                                        4 - 7 night minimum stay
                                        • 2 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                          1 Review
                                          Book it Now!
                                          3 - 7 night minimum stay
                                          • 2 BR,
                                          • 2 BA,
                                          • Sleeps 4
                                            1 Review
                                            Book it Now!
                                            2 - 4 night minimum stay
                                            • 1 BR,
                                            • 2 BA,
                                            • Sleeps 4
                                              $35,000
                                              per week
                                              Book it Now!
                                              14 night minimum stay
                                              • 3 BR,
                                              • 3 BA,
                                              • Sleeps 6
                                                $185 - $300
                                                per night
                                                5 - 14 night minimum stay
                                                • 2 BR,
                                                • 2 BA,
                                                • Sleeps 4
                                                  (6)
                                                  5 - 10 night minimum stay
                                                  • 2 BR,
                                                  • 2 BA,
                                                  • Sleeps 6
                                                    (25)
                                                    5 - 7 night minimum stay
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • Sleeps 6
                                                      (4)
                                                      Book it Now!
                                                      4 - 7 night minimum stay
                                                      • 1 BR,
                                                      • 2 BA,
                                                      • Sleeps 5
                                                        (6)
                                                        5 - 14 night minimum stay
                                                        • 3 BR,
                                                        • 3 BA,
                                                        • Sleeps 8
                                                          (5)
                                                          4 - 7 night minimum stay
                                                          • 1 BR,
                                                          • 2 BA,
                                                          • Sleeps 4
                                                            2 Reviews
                                                            Advertisement
                                                             

                                                            Recent Wailea Reviews

                                                            Great Location

                                                            4 of 5
                                                            The condo was excellent. it had everything that we needed for a comfortable stay. All inquiries to owner and property manager were quickly responded and very helpful. I had a little problem with the internet on the first day, but we got it resolved quickly.
                                                            • Submitted: Aug 4, 2014
                                                            • Stayed: Jul 2014

                                                            Stunning, amazing, perfect & I'm ready to go back

                                                            5 of 5
                                                            We had a fabulous stay at this house. It was exactly as advertised, only better. Because when you open up the glass siding doors and take in the ocean breeze and the gorgeous maui sunsets you will feel like you're in heaven. It's an easy 20 feet walk to a beautiful beach and you're right off a 1.5 mile walking/running trail that takes you right by the Fairmont, Grand Wailea & Four Seasons (you're in pretty good company when you stay here). We will be back for sure -- Janna, thank you so much for taking such great care of us. We're home and missing the house already!
                                                            • Submitted: Jul 27, 2014
                                                            • Stayed: Jul 2014

                                                            Wailea Perfection

                                                            5 of 5
                                                            My family and I spent several days in this condo, and I have to say that we can't think of one thing that wasn't awesome! I had the opportunity to check out two other units nearby, and they were no comparison to this quiet, corner unit on the golf course. We made great use of the lanai, for meals, reading, and had a couple friends over for a visit. The nature sounds were abundant, the colorful birds were fun to watch, and we even saw about 30 deer on the golf course early one evening. I was up at the crack of dawn taking sunrise photos with the outline of Haleakala in the background. Then again I was out outside shooting sunset photos with the beautiful cloud formations. The unit has two bedrooms with their own bathrooms. Beds were extremely comfortable and felt new. The air-conditioner cooled off the condo quickly so we were always comfortable. This unit is light and airy because it has windows on two sides of the unit. The kitchen was perfect for our needs, very well stocked. Trash and Recycle Bins are close by in the parking lot. Two nights, we walked down to the pool, grilled our dinner, and brought it back to the lanai to enjoy. We usually go to Costco after landing in Hawaii, and stock up for the week. We get some fresh fish and fruits, veggies and of course muffins! On many mornings, we would walk from the condo down to the Marriott Hotel, and go to the Starbucks there. And then we would walk along the long paved path next to the beach along the ocean. It is so beautiful. Regarding excursions, our favorite beach was McKenna's Big Beach. Just drive south for a few miles and you will see the sign for the McKenna State Park. Our favorite dinner (go at 4:30 to avoid waiting) was at Fred's Mexican Cafe in Kihei, open air, great food, great ambiance! One day, we got delicious sandwiches at the 808 Deli which is in the same complex as Fred's. As if that wasn't enough, the condo owner Sherrie, is a doll. So helpful and wonderful, and couldn't be nicer to deal with. We highly recommend this condo!! Thank you Sherrie! We'll be back!
                                                            • Submitted: Jul 6, 2014
                                                            • Stayed: Jun 2014