check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar
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!

Windward Cay: Houses, Villas & More (383)

  • 1 - 50 of 383
Additional fees apply. Taxes may be added.
    • 3 BR
    • 2 BA
    • Sleeps 6
    6
      • 3 BR
      • 2 BA
      • Sleeps 8
        • 3 BR
        • 2 BA
        • 2 HF BA
        • Sleeps 8
        4
          • 3 BR
          • 2 BA
          • Sleeps 8
          1 Review
            • 3 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 8
            2 Reviews
              NEW!
              • 3 BR
              • 2 BA
              • Sleeps 6
                • 3 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 8
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    1 Review
                      • 3 BR
                      • 2 BA
                      • Sleeps 6
                      13
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                          • 3 BR
                          • 2 BA
                          • Sleeps 7
                          1 Review
                            • 3 BR
                            • 2 BA
                            • Sleeps 8
                            2 Reviews
                              NEW!
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 7
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 7
                                      NEW!
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 8
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 6
                                          • 3 BR
                                          • 3 BA
                                          • Sleeps 8
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 6
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 7
                                                • 4 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 9
                                                9
                                                  • 3 BR
                                                  • 1 BA
                                                  • Sleeps 8
                                                  3
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 7
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          49
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              10
                                                                • 4 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 8
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • Sleeps 8
                                                                      Wonderful! 4.8/5
                                                                      (31 reviews)
                                                                      $60
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      31
                                                                        Excellent! 4.5/5
                                                                        (21 reviews)
                                                                        $69
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        21
                                                                          • 8 BR
                                                                          • 5 BA
                                                                          • Sleeps 18
                                                                          19
                                                                            NEW!
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                              • 8 BR
                                                                              • 5 BA
                                                                              • Sleeps 18
                                                                              3
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                  • 5 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 12
                                                                                  5
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 9
                                                                                    2 Reviews
                                                                                      • 6 BR
                                                                                      • 4 BA
                                                                                      • Sleeps 12
                                                                                        NEW!
                                                                                        • 6 BR
                                                                                        • 6 BA
                                                                                        • Sleeps 12
                                                                                          NEW!
                                                                                          • 6 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 16
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 9
                                                                                            4
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              1 Review
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                6
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 8
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                      NEW!
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 8
                                                                                                      • 1 - 50 of 383
                                                                                                       

                                                                                                      Recent Windward Cay Reviews

                                                                                                      Great Home!

                                                                                                      4 of 5
                                                                                                      I initially had concerns about my booking, however the management assured me everything would be fine and it was. The home is spacious and beautiful. We had a large group and the home accommodated us all well. I will remember this home for future travels to this area and I recommend it for other families as well.
                                                                                                      • Submitted: Sep 23, 2016
                                                                                                      • Stayed: Jul 2016

                                                                                                      Beautiful home

                                                                                                      5 of 5
                                                                                                      Beautiful home, looked exactly like the pictures. We came with a family of 11 and fit perfectly, my only complaint were the flat pillows and love bugs that met us at the front door. Other than that, the house was clean, and we enjoyed the pool every day of our stay.
                                                                                                      • Submitted: Sep 17, 2016
                                                                                                      • Stayed: Sep 2015

                                                                                                      Very clean, spacious and equipped

                                                                                                      5 of 5
                                                                                                      When we arrived at the villa it felt like home, very clean, spacious with great facilities and a lovely hamper which was great after a long flight. Very close to Restaurants, Walmart, Disney, Universal, Discovery Cove and shopping outlets. Free Wi-Fi and X-box games for my son. Enjoyed coming back to a dip in the pool after long days out.
                                                                                                      • Submitted: Aug 3, 2016
                                                                                                      • Stayed: Jul 2016