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.
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

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.

  • Showing 1-50 of 79
Additional service fee may apply.
  View Map Map
    Excellent! 4.4/5
    (8 reviews)
    avg/night
    • 4 BR
    • 3 BA
    • Sleeps 8
    Villa #1880380
    8
    Viewed 39 times in the last 48 hours
      Wonderful! 4.9/5
      (17 reviews)
      avg/night
      • 4 BR
      • 3 BA
      • Separate Toilet
      • Sleeps 8
      Villa #514188vb
      17
      Viewed 48 times in the last 48 hours
        Wonderful! 4.8/5
        (25 reviews)
        avg/night
        • 5 BR
        • 4 BA
        • Separate Toilet
        • Sleeps 12
        House #280384vb
        25
        Viewed 30 times in the last 48 hours
          Wonderful! 4.9/5
          (22 reviews)
          avg/night
          • 3 BR
          • 2 BA
          • Separate Toilet
          • Sleeps 8
          Townhome #622137vb
          22
          Viewed 33 times in the last 48 hours
            Excellent! 4.6/5
            (21 reviews)
            avg/night
            • 4 BR
            • 3 BA
            • Separate Toilet
            • Sleeps 10
            Villa #938346
            21
            Viewed 7 times in the last 48 hours
              • 5 BR
              • 5 BA
              • Sleeps 10
              House #6124220
              3
              Viewed 6 times in the last 48 hours
                avg/night
                • 4 BR
                • 3 BA
                • Separate Toilet
                • Sleeps 10
                House #6877692
                0
                Viewed 31 times in the last 48 hours
                  Exceptional! 5.0/5
                  (6 reviews)
                  avg/night
                  • 4 BR
                  • 3 BA
                  • Sleeps 8
                  Villa #1042254
                  6
                  Viewed 25 times in the last 48 hours
                    Wonderful! 4.8/5
                    (13 reviews)
                    avg/night
                    • 7 BR
                    • 4 BA
                    • Separate Toilet
                    • Sleeps 14
                    House #7116437
                    13
                    Viewed 25 times in the last 48 hours
                      Wonderful! 4.9/5
                      (21 reviews)
                      avg/night
                      • 5 BR
                      • 4 BA
                      • Separate Toilet
                      • Sleeps 10
                      Villa #922909
                      21
                      Viewed 12 times in the last 48 hours
                        Excellent! 4.7/5
                        (23 reviews)
                        avg/night
                        • 8 BR
                        • 4 BA
                        • Separate Toilet
                        • Sleeps 18
                        Villa #3656206
                        23
                        Viewed 56 times in the last 48 hours
                          Wonderful! 4.9/5
                          (100 reviews)
                          avg/night
                          • 5 BR
                          • 4 BA
                          • Separate Toilet
                          • Sleeps 12
                          Villa #58577vb
                          100
                          Viewed 24 times in the last 48 hours
                            Exceptional! 5.0/5
                            (14 reviews)
                            avg/night
                            • 5 BR
                            • 5 BA
                            • Sleeps 10
                            Villa #8005937
                            14
                            Viewed 17 times in the last 48 hours
                              avg/night
                              • 3 BR
                              • 2 BA
                              • Separate Toilet
                              • Sleeps 6
                              Townhome #4045075
                              3
                              Viewed 19 times in the last 48 hours
                                avg/night
                                • 7 BR
                                • 4 BA
                                • Separate Toilets
                                • Sleeps 18
                                Villa #3592246
                                3
                                Viewed 43 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (5 reviews)
                                  avg/night
                                  • 8 BR
                                  • 4 BA
                                  • Separate Toilet
                                  • Sleeps 18
                                  House #4086969
                                  5
                                  Viewed 45 times in the last 48 hours
                                    • 7 BR
                                    • 4 BA
                                    • Separate Toilet
                                    • Sleeps 14
                                    House #915875vb
                                    2
                                    Viewed 69 times in the last 48 hours
                                      avg/night
                                      • 5 BR
                                      • 5 BA
                                      • Sleeps 12
                                      House #65704vb
                                      3
                                      Viewed 14 times in the last 48 hours
                                        • 5 BR
                                        • 5 BA
                                        • Sleeps 10
                                        Villa #983204vb
                                        0
                                        Viewed 27 times in the last 48 hours
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 10
                                          Villa #3950764
                                          0
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 8
                                            House #899917vb
                                            1
                                            Viewed 20 times in the last 48 hours
                                              • 4 BR
                                              • 3 BA
                                              • Sleeps 9
                                              House #4266867
                                              1
                                                avg/night
                                                • 5 BR
                                                • 4 BA
                                                • Separate Toilet
                                                • Sleeps 10
                                                House #4289367
                                                0
                                                Viewed 86 times in the last 48 hours
                                                  • 4 BR
                                                  • 3 BA
                                                  • Separate Toilet
                                                  • Sleeps 8
                                                  Villa #925353vb
                                                  0
                                                    Wonderful! 4.9/5
                                                    (15 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    House #123767vb
                                                    15
                                                    Viewed 21 times in the last 48 hours
                                                      Excellent! 4.3/5
                                                      (13 reviews)
                                                      avg/night
                                                      • 7 BR
                                                      • 4 BA
                                                      • Separate Toilet
                                                      • Sleeps 16
                                                      Villa #314848vb
                                                      13
                                                      Viewed 111 times in the last 48 hours
                                                        avg/night
                                                        • 4 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        Villa #4177087
                                                        0
                                                        Viewed 8 times in the last 48 hours
                                                          • 4 BR
                                                          • 3 BA
                                                          • Separate Toilet
                                                          • Sleeps 10
                                                          House #4242694
                                                          1
                                                            avg/night
                                                            • 4 BR
                                                            • 3 BA
                                                            • Sleeps 8
                                                            House #899915vb
                                                            0
                                                            Viewed 8 times in the last 48 hours
                                                              • 5 BR
                                                              • 4 BA
                                                              • Separate Toilet
                                                              • Sleeps 10
                                                              House #819357vb
                                                              9
                                                                • 4 BR
                                                                • 4 BA
                                                                • Sleeps 9
                                                                Villa #4325542
                                                                0
                                                                  Wonderful! 4.8/5
                                                                  (5 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 4 BA
                                                                  • Separate Toilet
                                                                  • Sleeps 12
                                                                  Villa #3939350
                                                                  5
                                                                  Viewed 32 times in the last 48 hours
                                                                    avg/night
                                                                    • 5 BR
                                                                    • 4 BA
                                                                    • Sleeps 10
                                                                    House #983335vb
                                                                    0
                                                                    Viewed 5 times in the last 48 hours
                                                                      • 4 BR
                                                                      • 4 BA
                                                                      • Sleeps 8
                                                                      House #4310365
                                                                      0
                                                                        avg/night
                                                                        • 5 BR
                                                                        • 4 BA
                                                                        • Sleeps 12
                                                                        Villa #4213327
                                                                        0
                                                                        Viewed 7 times in the last 48 hours
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 8
                                                                          House #4366475
                                                                          4
                                                                          Viewed 36 times in the last 48 hours
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 1 BA
                                                                            • Sleeps 10
                                                                            House #4439241
                                                                            0
                                                                            Viewed 5 times in the last 48 hours
                                                                              • 5 BR
                                                                              • 4 BA
                                                                              • Sleeps 4
                                                                              House #997467vb
                                                                              0
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                House #930978vb
                                                                                0
                                                                                  • 4 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 8
                                                                                  House #4313521
                                                                                  0
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 8
                                                                                    House #4313534
                                                                                    0
                                                                                      • 5 BR
                                                                                      • 5 BA
                                                                                      • Sleeps 10
                                                                                      House #4426691
                                                                                      0
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        House #3807701
                                                                                        5
                                                                                          avg/night
                                                                                          • 6 BR
                                                                                          • 4 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 12
                                                                                          House #977329vb
                                                                                          0
                                                                                          Viewed 18 times in the last 48 hours
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 8
                                                                                            Villa #736788vb
                                                                                            0
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              Villa #4279047
                                                                                              0
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                House #4135465
                                                                                                0
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  Townhome #4353803
                                                                                                  0
                                                                                                    • 4 BR
                                                                                                    • 4 BA
                                                                                                    • Sleeps 8
                                                                                                    House #4297913
                                                                                                    0
                                                                                                      • 5 BR
                                                                                                      • 4 BA
                                                                                                      • Separate Toilet
                                                                                                      • Sleeps 12
                                                                                                      House #650540vb
                                                                                                      0
                                                                                                      Viewed 9 times in the last 48 hours
                                                                                                      • 1 - 50 of 79
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Fabulous Villa

                                                                                                      5 of 5
                                                                                                      We have been to a few villas but this is by far the best. The photos just do not do the property justice. The quality of the home and facilities are superb. There are lots of home comforts and the attention to detail is outstanding including le creuset, Denby, crystal glassware and many more. All of the furniture is of the highest quality and the beds offer a wonderful nights sleep. The games room is the icing on the cake. You will not find a better villa. We will be back!
                                                                                                      • Review Submitted: 09-Jan-2017
                                                                                                      • Date of Stay: Nov 2016

                                                                                                      spacious , great location , great value for money

                                                                                                      5 of 5
                                                                                                      We stayed at this villa for 2 weeks the villa was very spacious and comfortable and well equipped it's 5 mins from shops and restaunts at champions gate and the i4 to Disney . We found the villa very good value for money . The owner is very quick to react if something is wrong so that your holiday runs smoothly would def recommend villa and will be returning ourselves
                                                                                                      • Review Submitted: 06-Dec-2016
                                                                                                      • Date of Stay: Nov 2016

                                                                                                      House was in a great area close to I4 and shops and restaurants.

                                                                                                      4 of 5
                                                                                                      The house was a fantastic size the pool and games room were great fun, for my family. The bedrooms are very spacious,as is the downstairs. I like to thank the owners Kate & Jeff I needed to contact them and they was only a phone call or email away very helpful. Was very close to the I4 so easy access to get to the theme parks. There's a Walmart only 20 minute drive away or a publix 10 minute drive away so close for all your needs😀 Thanks again Kate & Jeff The Gadsden family
                                                                                                      • Review Submitted: 22-Aug-2016
                                                                                                      • Date of Stay: Aug 2016