HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon 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 svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled

Holidaymakers searching for holiday rentals in Windwood Bay also enquired about villas in Calabay Parc, villas in Highlands Reserve and villas in Tuscan Ridge

Make a holiday rental home or villa in Windward Bay, Florida your home away from home

Windward Bay is a beautiful community in the Orlando countryside in Florida. Centrally located and filled with beautifully luxurious villas, Windward Bay, Florida is a wonderful base for any Florida holiday, from golfing breaks to romantic getaways in the sun, but the magnificent access to all the theme parks and attractions of the Orlando region ensure that family holidays are always exceptional fun.

Things to do in Windward Bay, Florida

Windward Bay is surrounded by conservation areas, blissfully clear lakes and open woodlands, which make Windward Bay villas hugely relaxing places to stay. There are some wonderful walks to enjoy around Lake Madison from Windward Bay, as well as a great range of nature trails. Horse riding trips, boat tours and even indoor skydiving can be arranged locally.

The theme parks of Orlando attract hundreds of thousands of visitors to the region each year, and a Windward Bay villa is a fantastically peaceful spot from which to enjoy the huge attractions with your family, yet remain cut off from the crowds, allowing you to really relax once you leave the parks behind you. The new Disneyworld ticketing system means that you can return home as many times as you like during the day without incurring any penalties. Windward Bay villas are just 10 minutes from Disneyworld, and just 15 minutes from Universal Studios, Wet n’Wild, Aquatica, Sea World and Magic Kingdom. Daytona and the Kennedy Space Centre are within an hour’s drive too.

Many people take Windward Bay villas for the golf. Florida, and especially the Orlando region, is famous for its golfing credentials, which are world class. There are a great range of golf courses in the area, the finest of which are simply stunning, with beautiful landscaping, challenging greens and obstacle strewn fairways that will provide a real test of your golf. Any standard of golfer will be able to find a good challenge, the best of which is Champions Gate, just minutes from the front gates of Windward Bay.

Places to visit on holiday in Windward Bay, Florida

A holiday rental villa in Windward Bay is just 50km from the glorious white beaches of the Atlantic Coast. Cocoa Beach, which is one of the most beautiful in Florida is a sensational place to sunbathe, sail, swim, go deep sea fishing or simply soak up the atmosphere.

Weather in Windward Bay, Florida

Florida is a magnificent holiday destination throughout the year. With average monthly temperatures ranging between 31˚C (July and August) and 21˚C (December and January), temperatures are always hot and rain rare. Golf holidays are superb at any time of year, and visiting the theme parks is often best just outside the peak months as the crowds are greatly reduced.

Travel to Windward Bay, Florida

British Airways and Virgin Atlantic make it wonderfully easy to reach a holiday rental in Windward Bay. A hire car is an essential asset when staying in Windward Bay accommodation, and they are easily arranged at the airport, which is just 30km away.

Favorite
    Viewed 39 times in the last 48 hours
    • 4 bedrooms
    • 3 bathrooms
    • Sleeps 8
    Favorite
      Viewed 12 times in the last 48 hours
      • 4 bedrooms
      • 3 bathrooms
      • Separate Toilet
      • Sleeps 8
      Favorite
        Viewed 34 times in the last 48 hours
        • 4 bedrooms
        • 3 bathrooms
        • Separate Toilet
        • Sleeps 10
        Favorite
          Viewed 9 times in the last 48 hours
          • 4 bedrooms
          • 3 bathrooms
          • Separate Toilet
          • Sleeps 10
          Favorite
            Viewed 26 times in the last 48 hours
            • 7 bedrooms
            • 4 bathrooms
            • Separate Toilet
            • Sleeps 14
            Favorite
              Viewed 14 times in the last 48 hours
              • 5 bedrooms
              • 4 bathrooms
              • Separate Toilet
              • Sleeps 12
              Favorite
                Viewed 11 times in the last 48 hours
                • 4 bedrooms
                • 3 bathrooms
                • Sleeps 8
                Favorite
                  • 4 bedrooms
                  • 3 bathrooms
                  • Separate Toilet
                  • Sleeps 10
                  Favorite
                    Viewed 69 times in the last 48 hours
                    • 5 bedrooms
                    • 4 bathrooms
                    • Separate Toilet
                    • Sleeps 10
                    Favorite
                      Viewed 22 times in the last 48 hours
                      • 3 bedrooms
                      • 2 bathrooms
                      • Separate Toilet
                      • Sleeps 8
                      Favorite
                        Viewed 57 times in the last 48 hours
                        • 7 bedrooms
                        • 4 bathrooms
                        • Separate Toilet
                        • Sleeps 14
                        Favorite
                          Viewed 10 times in the last 48 hours
                          • 4 bedrooms
                          • 3 bathrooms
                          • Sleeps 8
                          Favorite
                            Viewed 22 times in the last 48 hours
                            • 7 bedrooms
                            • 4 bathrooms
                            • Separate Toilet
                            • Sleeps 16
                            Favorite
                              • 5 bedrooms
                              • 4 bathrooms
                              • Separate Toilet
                              • Sleeps 10
                              Favorite
                                Viewed 8 times in the last 48 hours
                                • 3 bedrooms
                                • 2 bathrooms
                                • Separate Toilet
                                • Sleeps 6
                                Favorite
                                  • 5 bedrooms
                                  • 5 bathrooms
                                  • Sleeps 10
                                  Favorite
                                    Viewed 18 times in the last 48 hours
                                    • 4 bedrooms
                                    • 3 bathrooms
                                    • Separate Toilet
                                    • Sleeps 10
                                    Favorite
                                      Viewed 14 times in the last 48 hours
                                      • 7 bedrooms
                                      • 4 bathrooms
                                      • Separate Toilets
                                      • Sleeps 18
                                      Favorite
                                        • 5 bedrooms
                                        • 5 bathrooms
                                        • Sleeps 10
                                        Favorite
                                          Viewed 29 times in the last 48 hours
                                          • 5 bedrooms
                                          • 4 bathrooms
                                          • Separate Toilet
                                          • Sleeps 12
                                          Favorite
                                            Viewed 11 times in the last 48 hours
                                            • 5 bedrooms
                                            • 4 bathrooms
                                            • Sleeps 12
                                            Favorite
                                              Viewed 19 times in the last 48 hours
                                              • 8 bedrooms
                                              • 4 bathrooms
                                              • Separate Toilet
                                              • Sleeps 18
                                              Favorite
                                                • 5 bedrooms
                                                • 4 bathrooms
                                                • Sleeps 12
                                                Favorite
                                                  Viewed 6 times in the last 48 hours
                                                  • 4 bedrooms
                                                  • 3 bathrooms
                                                  • Sleeps 9
                                                  Favorite
                                                    • 4 bedrooms
                                                    • 3 bathrooms
                                                    • Sleeps 8
                                                    Favorite
                                                      Viewed 31 times in the last 48 hours
                                                      • 5 bedrooms
                                                      • 4 bathrooms
                                                      • Separate Toilet
                                                      • Sleeps 10
                                                      Favorite
                                                        Viewed 25 times in the last 48 hours
                                                        • 7 bedrooms
                                                        • 4 bathrooms
                                                        • Separate Toilets
                                                        • Sleeps 16
                                                        Favorite
                                                          Viewed 10 times in the last 48 hours
                                                          • 5 bedrooms
                                                          • 4 bathrooms
                                                          • Separate Toilet
                                                          • Sleeps 10
                                                          Favorite
                                                            Viewed 8 times in the last 48 hours
                                                            • 4 bedrooms
                                                            • 3 bathrooms
                                                            • Sleeps 8
                                                            Favorite
                                                              Viewed 7 times in the last 48 hours
                                                              • 4 bedrooms
                                                              • 3 bathrooms
                                                              • Separate Toilet
                                                              • Sleeps 8
                                                              Favorite
                                                                • 5 bedrooms
                                                                • 3 bathrooms
                                                                • Sleeps 10
                                                                Favorite
                                                                  Viewed 5 times in the last 48 hours
                                                                  • 5 bedrooms
                                                                  • 3 bathrooms
                                                                  • Sleeps 10
                                                                  Favorite
                                                                    • 5 bedrooms
                                                                    • 4 bathrooms
                                                                    • Separate Toilet
                                                                    • Sleeps 10
                                                                    Favorite
                                                                      Viewed 7 times in the last 48 hours
                                                                      • 5 bedrooms
                                                                      • 4 bathrooms
                                                                      • Separate Toilet
                                                                      • Sleeps 10
                                                                      Favorite
                                                                        • 5 bedrooms
                                                                        • 4 bathrooms
                                                                        • Separate Toilet
                                                                        • Sleeps 10
                                                                        Favorite
                                                                          Viewed 12 times in the last 48 hours
                                                                          • 8 bedrooms
                                                                          • 4 bathrooms
                                                                          • Separate Toilet
                                                                          • Sleeps 18
                                                                          Favorite
                                                                            • 4 bedrooms
                                                                            • 3 bathrooms
                                                                            • Sleeps 8
                                                                            Favorite
                                                                              • 4 bedrooms
                                                                              • 4 bathrooms
                                                                              • Sleeps 9
                                                                              Favorite
                                                                                • 5 bedrooms
                                                                                • 4 bathrooms
                                                                                • Separate Toilet
                                                                                • Sleeps 12
                                                                                Favorite
                                                                                  • 8 bedrooms
                                                                                  • 4 bathrooms
                                                                                  • Separate Toilet
                                                                                  • Sleeps 18
                                                                                  Favorite
                                                                                    • 4 bedrooms
                                                                                    • 3 bathrooms
                                                                                    • Sleeps 8
                                                                                    Favorite
                                                                                      • 5 bedrooms
                                                                                      • 4 bathrooms
                                                                                      • Sleeps 10
                                                                                      Favorite
                                                                                        Viewed 8 times in the last 48 hours
                                                                                        • 5 bedrooms
                                                                                        • 4 bathrooms
                                                                                        • Sleeps 12
                                                                                        Favorite
                                                                                          • 4 bedrooms
                                                                                          • 3 bathrooms
                                                                                          • Separate Toilet
                                                                                          • Sleeps 8
                                                                                          Favorite
                                                                                            • 5 bedrooms
                                                                                            • 4 bathrooms
                                                                                            • Separate Toilet
                                                                                            • Sleeps 12
                                                                                            Favorite
                                                                                              • 5 bedrooms
                                                                                              • 4 bathrooms
                                                                                              • Separate Toilet
                                                                                              • Sleeps 10
                                                                                              Favorite
                                                                                                • 4 bedrooms
                                                                                                • 3 bathrooms
                                                                                                • Sleeps 8
                                                                                                Favorite
                                                                                                  • 4 bedrooms
                                                                                                  • 3 bathrooms
                                                                                                  • Sleeps 8
                                                                                                  Favorite
                                                                                                    • 5 bedrooms
                                                                                                    • 3 bathrooms
                                                                                                    • Sleeps 10
                                                                                                    Favorite
                                                                                                      • 4 bedrooms
                                                                                                      • 3 bathrooms
                                                                                                      • Sleeps 10
                                                                                                      • 1 - 50 of 97
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Absolutely perfect

                                                                                                      5 of 5
                                                                                                      We stayed here from 8 April - 22 April. We took our 3 children, 11,12 and 18 and my Mom and Dad. It was perfect for us, we loved the heated pool and the rooms were great. We got married at Paradise Cove on the 13th and also managed to visit 11 parks, so very busy holiday. Karen, the owner was very helpful and friendly with all of my enquiries before we went too and very kindly left a bottle of bubbly for wedding. I would recommend this house to anyone with family or group of friends, there is plenty of room for upto 10 people. Lovely, thank you Karen, it made our wedding and holiday perfect x
                                                                                                      • Review Submitted: May 03, 2017
                                                                                                      • Date of Stay: Apr 2017

                                                                                                      The house met our needs as a family of 4 with 2 kids aged 8 & 11 perfectly.

                                                                                                      5 of 5
                                                                                                      The house was presented to a very high standard and was ideally located in a residential location within 15-20mins of the Disney Parks.
                                                                                                      • Review Submitted: Apr 21, 2017
                                                                                                      • Date of Stay: Apr 2017