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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 78
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    Excellent! 4.4/5
    (8 reviews)
    avg/night
    • 4 BR
    • 3 BA
    • Sleeps 8
    Villa #1880380
    8
    Viewed 25 times in the last 48 hours
      Wonderful! 4.9/5
      (18 reviews)
      avg/night
      • 4 BR
      • 3 BA
      • Separate Toilet
      • Sleeps 8
      Villa #514188vb
      18
      Viewed 29 times in the last 48 hours
        avg/night
        • 4 BR
        • 3 BA
        • Separate Toilet
        • Sleeps 10
        House #6877692
        2
        Viewed 24 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 27 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 20 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 13 times in the last 48 hours
                Exceptional! 5.0/5
                (6 reviews)
                avg/night
                • 4 BR
                • 3 BA
                • Sleeps 8
                Villa #1042254
                6
                Viewed 30 times in the last 48 hours
                  Exceptional! 5.0/5
                  (15 reviews)
                  avg/night
                  • 5 BR
                  • 5 BA
                  • Sleeps 10
                  Villa #8005937
                  15
                  Viewed 21 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 31 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 17 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 35 times in the last 48 hours
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Separate Toilet
                          • Sleeps 6
                          Townhome #4045075
                          3
                          Viewed 12 times in the last 48 hours
                            Wonderful! 4.9/5
                            (102 reviews)
                            avg/night
                            • 5 BR
                            • 4 BA
                            • Separate Toilet
                            • Sleeps 12
                            Villa #58577vb
                            102
                            Viewed 35 times in the last 48 hours
                              avg/night
                              • 7 BR
                              • 4 BA
                              • Separate Toilets
                              • Sleeps 18
                              Villa #3592246
                              3
                              Viewed 29 times in the last 48 hours
                                • 5 BR
                                • 5 BA
                                • Sleeps 10
                                House #6124220
                                3
                                Viewed 8 times in the last 48 hours
                                  • 7 BR
                                  • 4 BA
                                  • Separate Toilet
                                  • Sleeps 14
                                  House #915875vb
                                  3
                                  Viewed 39 times in the last 48 hours
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 8
                                    House #4366475
                                    4
                                    Viewed 33 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 191 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 19 times in the last 48 hours
                                          • 5 BR
                                          • 4 BA
                                          • Sleeps 12
                                          Villa #4213327
                                            avg/night
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 9
                                            House #4266867
                                            1
                                            Viewed 5 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (5 reviews)
                                              avg/night
                                              • 5 BR
                                              • 4 BA
                                              • Separate Toilet
                                              • Sleeps 12
                                              Villa #3939350
                                              5
                                              Viewed 24 times in the last 48 hours
                                                avg/night
                                                • 5 BR
                                                • 5 BA
                                                • Sleeps 12
                                                House #65704vb
                                                3
                                                Viewed 11 times in the last 48 hours
                                                  • 5 BR
                                                  • 5 BA
                                                  • Sleeps 10
                                                  Villa #983204vb
                                                    • 5 BR
                                                    • 4 BA
                                                    • Separate Toilet
                                                    • Sleeps 10
                                                    House #4444259
                                                      • 4 BR
                                                      • 3 BA
                                                      • Sleeps 8
                                                      House #899917vb
                                                      1
                                                      Viewed 27 times in the last 48 hours
                                                        avg/night
                                                        • 5 BR
                                                        • 4 BA
                                                        • Separate Toilet
                                                        • Sleeps 10
                                                        House #4289367
                                                        Viewed 62 times in the last 48 hours
                                                          • 4 BR
                                                          • 3 BA
                                                          • Separate Toilet
                                                          • Sleeps 8
                                                          Villa #925353vb
                                                            • 5 BR
                                                            • 3 BA
                                                            • Sleeps 10
                                                            Villa #6872309
                                                              • 5 BR
                                                              • 3 BA
                                                              • Sleeps 10
                                                              Villa #996746vb
                                                              Viewed 15 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (16 reviews)
                                                                avg/night
                                                                • 4 BR
                                                                • 3 BA
                                                                • Sleeps 8
                                                                House #123767vb
                                                                16
                                                                Viewed 21 times in the last 48 hours
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 8
                                                                  Villa #4177087
                                                                  1
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • Separate Toilet
                                                                    • Sleeps 10
                                                                    House #4242694
                                                                    1
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 8
                                                                      House #899915vb
                                                                      Viewed 17 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (9 reviews)
                                                                        avg/night
                                                                        • 5 BR
                                                                        • 4 BA
                                                                        • Separate Toilet
                                                                        • Sleeps 10
                                                                        House #819357vb
                                                                        9
                                                                        Viewed 5 times in the last 48 hours
                                                                          • 4 BR
                                                                          • 4 BA
                                                                          • Sleeps 9
                                                                          Villa #4325542
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 4 BA
                                                                            • Sleeps 12
                                                                            House #6955440
                                                                            Viewed 9 times in the last 48 hours
                                                                              • 5 BR
                                                                              • 1 BA
                                                                              • Sleeps 10
                                                                              House #4439241
                                                                                • 5 BR
                                                                                • 4 BA
                                                                                • Sleeps 10
                                                                                House #983335vb
                                                                                  • 4 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 8
                                                                                  House #4310365
                                                                                    • 5 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 4
                                                                                    House #997467vb
                                                                                      • 5 BR
                                                                                      • 4 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 12
                                                                                      House #4442058
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        House #930978vb
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 8
                                                                                          Villa #4279047
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 8
                                                                                            House #4313521
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              Villa #736788vb
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                House #4313534
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 8
                                                                                                  House #4135465
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 8
                                                                                                    House #3807701
                                                                                                    5
                                                                                                      avg/night
                                                                                                      • 6 BR
                                                                                                      • 4 BA
                                                                                                      • Separate Toilet
                                                                                                      • Sleeps 12
                                                                                                      House #977329vb
                                                                                                      Viewed 11 times in the last 48 hours
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                                                                                                      Recent Reviews

                                                                                                      The Perfect Christmas Holiday

                                                                                                      5 of 5
                                                                                                      We stayed at this home during Christmas week of 2016. It was absolutely amazing in every way. This was our 3rd home that we have rented in Orlando and this was hands-down the best. Our family of 3 stayed here with my wife’s mother and younger niece and grown nephew. There is so much living area in this house that everyone had a chance to have their own alone-time. Every bedroom has their own TV and 3 of them even have their own en-suite bathrooms. The beds were very comfortable. The kids absolutely loved the pool and the hot tub was so warm. Being December, it was so worth getting the pool heat. As a tip, it takes about 15 minutes for the hot tub to fully warm up so start it a few minutes before getting in. The kids loved playing with the geckos that would hang out on the outside of the pool screen. The pool area is so private since the home is on a cul-de-sac, there is nothing directly behind the home and there are hedges around the screen. You feel like you are in your own tropical paradise. We cooked and grilled at the house every day and loved the top-notch cookware and tons of different utensils and such. Everything that we needed was already there. It was so nice that the house was perfectly clean and we didn’t see one bug, which is really saying something in Florida. To top it off, the owner, Denise, was really responsive and was a pleasure to deal with. We only dealt with the management company once, but they were also good too. All of us had a great time and would highly recommend Denise’s home.
                                                                                                      • Review Submitted: 23-Jan-2017
                                                                                                      • Date of Stay: Dec 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