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

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.

Cancel Clear Filters Apply Filters

Property Type

Popular Searches

Payment Options

Facilities

Managed By

Local Area

Property Details

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • Showing 1-50 of 75
Additional service fee may apply.
    Excellent! 4.3/5
    (7 reviews)
    avg/night
    • 4 BR
    • 3 BA
    • Sleeps 8
    Villa #1880380
    7
    Viewed 16 times in the last 48 hours
      Wonderful! 4.9/5
      (21 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Separate Toilet
      • Sleeps 8
      Townhome #622137vb
      21
      Viewed 17 times in the last 48 hours
        • 5 BR
        • 4 BA
        • Separate Toilet
        • Sleeps 12
        House #664723vb
        Viewed 5 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 10 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 15 times in the last 48 hours
              • 5 BR
              • 5 BA
              • Sleeps 10
              House #6124220
              2 Reviews
              Viewed 10 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 12 times in the last 48 hours
                  Excellent! 4.7/5
                  (22 reviews)
                  avg/night
                  • 8 BR
                  • 4 BA
                  • Separate Toilet
                  • Sleeps 18
                  Villa #3656206
                  22
                  Viewed 15 times in the last 48 hours
                    avg/night
                    • 4 BR
                    • 3 BA
                    • Separate Toilet
                    • Sleeps 10
                    House #6877692
                    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 7 times in the last 48 hours
                        Wonderful! 4.8/5
                        (12 reviews)
                        avg/night
                        • 7 BR
                        • 4 BA
                        • Separate Toilet
                        • Sleeps 14
                        House #7116437
                        12
                        Viewed 6 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 8 times in the last 48 hours
                            • 5 BR
                            • 4 BA
                            • Separate Toilet
                            • Sleeps 10
                            Villa #8005937
                            13
                              avg/night
                              • 7 BR
                              • 4 BA
                              • Separate Toilets
                              • Sleeps 18
                              Villa #3592246
                              3
                              Viewed 22 times in the last 48 hours
                                • 8 BR
                                • 4 BA
                                • Separate Toilet
                                • Sleeps 18
                                House #4086969
                                4
                                Viewed 15 times in the last 48 hours
                                  • 7 BR
                                  • 4 BA
                                  • Separate Toilet
                                  • Sleeps 14
                                  House #915875vb
                                  Viewed 36 times in the last 48 hours
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Separate Toilet
                                    • Sleeps 6
                                    Townhome #4045075
                                    3
                                    Viewed 15 times in the last 48 hours
                                      • 5 BR
                                      • 4 BA
                                      • Sleeps 12
                                      House #356234
                                      1 Review
                                        • 5 BR
                                        • 5 BA
                                        • Sleeps 12
                                        House #65704vb
                                        3
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 10
                                          Villa #3950764
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 8
                                            House #899917vb
                                            Viewed 6 times in the last 48 hours
                                              • 4 BR
                                              • 3 BA
                                              • Sleeps 9
                                              House #4266867
                                                avg/night
                                                • 5 BR
                                                • 4 BA
                                                • Separate Toilet
                                                • Sleeps 10
                                                House #4289367
                                                Viewed 15 times in the last 48 hours
                                                  • 4 BR
                                                  • 3 BA
                                                  • Separate Toilet
                                                  • Sleeps 8
                                                  Villa #925353vb
                                                    • 5 BR
                                                    • 4 BA
                                                    • Separate Toilet
                                                    • Sleeps 10
                                                    House #819357vb
                                                    8
                                                      • 5 BR
                                                      • 4 BA
                                                      • Separate Toilet
                                                      • Sleeps 12
                                                      Villa #3939350
                                                      5
                                                        • 4 BR
                                                        • 3 BA
                                                        • Separate Toilet
                                                        • Sleeps 10
                                                        House #4242694
                                                        1 Review
                                                          • 5 BR
                                                          • 4 BA
                                                          • Sleeps 12
                                                          Villa #4213327
                                                            • 4 BR
                                                            • 3 BA
                                                            • Sleeps 8
                                                            House #930978vb
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              Villa #4177087
                                                                • 4 BR
                                                                • 3 BA
                                                                • Sleeps 8
                                                                House #4313521
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 4 BA
                                                                  • Sleeps 8
                                                                  House #4310365
                                                                  Viewed 10 times in the last 48 hours
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • Sleeps 10
                                                                    Villa #4318427
                                                                    Viewed 6 times in the last 48 hours
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 8
                                                                      House #4135465
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                        Villa #4279047
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 8
                                                                          House #4313534
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            Villa #736788vb
                                                                              • 5 BR
                                                                              • 4 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 10
                                                                              House #650540vb
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                House #753403vb
                                                                                  • 4 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 8
                                                                                  House #4297913
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 8
                                                                                    Villa #4140032
                                                                                      • 5 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 10
                                                                                      Villa #6872309
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        House #6789082
                                                                                          • 4 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 9
                                                                                          Villa #4325542
                                                                                            • 5 BR
                                                                                            • 4 BA
                                                                                            • Sleeps 10
                                                                                            Villa #4338252
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              Villa #4313217
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                Villa #4255686
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 8
                                                                                                  House #3807701
                                                                                                  5
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 8
                                                                                                    House #4313216
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 8
                                                                                                      Villa #4301303
                                                                                                      • 1 - 50 of 75
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Lovely villa not far from all the Disney parks.

                                                                                                      5 of 5
                                                                                                      We thoroughly enjoyed our stay in this lovely villa. The house had everything for a comfortable holiday and the owner was super at getting back with answers to questions.
                                                                                                      • Review Submitted: 31-Oct-2016
                                                                                                      • Date of Stay: Oct 2016

                                                                                                      Fabulous accommodation - Our best find ever!

                                                                                                      5 of 5
                                                                                                      Well presented, luxury villa, spotlessly clean. 3 large bedrooms with ensuites and a further 2 twins with another bathroom. 3 lounges in case of arguments and time out needed! Plenty of TVs/DVDs. Lovely pool and jacuzzi with good quality outdoor furniture and fun games room with snooker/pool table and table tennis table. Plenty of crockery (Denby) and towels/sheets from John Lewis. Pool towels also available and a large washing machine/dryer. Excellent location - 15 mins south of Disney and 30 mins south of Universal. 5 mins from Championsgate with Publix, a pizza/chinese with delivery and our latest find, Chilis (American diner). We have stayed in many self-catering villas and this has to be the best. Can't recommend it highly enough.
                                                                                                      • Review Submitted: 07-Oct-2016
                                                                                                      • Date of Stay: Sep 2016

                                                                                                      amazing

                                                                                                      5 of 5
                                                                                                      perfect location in a fantastic home which has the right amount of care and attention from the owner and the property management team- I would highly recommend this house and it is very close to all the attractions but far enough away to be peaceful- massive thumbs up from all the family- kids wanted to move in!!!
                                                                                                      • Review Submitted: 21-Apr-2016
                                                                                                      • Date of Stay: Mar 2016