Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Homes
Townhomes
Villas
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Cottages
Estates
Farmhouses
Hotels
Lodges
Studios
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Windsor Hills Villa Rentals(234)

234 Results
Book it Now!
1 - 4 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 9
    (21)
    Book it Now!
    3 - 7 night minimum stay
    • 6 BR,
    • 4 BA,
    • Sleeps 14
      (17)
      Book it Now!
      3 night minimum stay
      • 4 BR,
      • 4 BA,
      • Sleeps 8
        (7)
        Book it Now!
        4 night minimum stay
        • 6 BR,
        • 4 BA,
        • Sleeps 15
          (6)
          Book it Now!
          4 night minimum stay
          • 4 BR,
          • 4 BA,
          • Sleeps 10
            (16)
            3 - 7 night minimum stay
            • 6 BR,
            • 4 BA,
            • Sleeps 16
              (17)
              Book it Now!
              3 - 7 night minimum stay
              • 6 BR,
              • 4 BA,
              • Sleeps 14
                (6)
                Book it Now!
                3 - 5 night minimum stay
                • 6 BR,
                • 4 BA,
                • Sleeps 12
                  (4)
                  Book it Now!
                  3 - 10 night minimum stay
                  • 6 BR,
                  • 4 BA,
                  • Sleeps 12
                    Book it Now!
                    5 night minimum stay
                    • 4 BR,
                    • 4 BA,
                    • Sleeps 10
                      (3)
                      Book it Now!
                      3 night minimum stay
                      • 6 BR,
                      • 4 BA,
                      • Sleeps 14
                        $225 - $370
                        per night
                        Book it Now!
                        3 - 7 night minimum stay
                        • 4 BR,
                        • 4 BA,
                        • Sleeps 10
                          Book it Now!
                          3 - 7 night minimum stay
                          • 5 BR,
                          • 5 BA,
                          • Sleeps 12
                            1 Review
                            Book it Now!
                            3 - 10 night minimum stay
                            • 6 BR,
                            • 4 BA,
                            • Sleeps 12
                              3 - 7 night minimum stay
                              • 5 BR,
                              • 5 BA,
                              • Sleeps 10
                                (9)
                                Book it Now!
                                7 night minimum stay
                                • 4 BR,
                                • 4 BA,
                                • Sleeps 10
                                  $215 - $375
                                  per night
                                  Book it Now!
                                  3 night minimum stay
                                  • 4 BR,
                                  • 4 BA,
                                  • Sleeps 10
                                    Book it Now!
                                    3 - 7 night minimum stay
                                    • 5 BR,
                                    • 5 BA,
                                    • Sleeps 10
                                      Book it Now!
                                      3 night minimum stay
                                      • 6 BR,
                                      • 4 BA,
                                      • Sleeps 14
                                        Book it Now!
                                        3 night minimum stay
                                        • 5 BR,
                                        • 5 BA,
                                        • Sleeps 10
                                          Book it Now!
                                          3 night minimum stay
                                          • 5 BR,
                                          • 5 BA,
                                          • Sleeps 10
                                            Book it Now!
                                            3 night minimum stay
                                            • 5 BR,
                                            • 5 BA,
                                            • Sleeps 12
                                              Book it Now!
                                              3 night minimum stay
                                              • 5 BR,
                                              • 3 BA,
                                              • Sleeps 12
                                                Book it Now!
                                                3 night minimum stay
                                                • 4 BR,
                                                • 4 BA,
                                                • Sleeps 8
                                                  Book it Now!
                                                  3 night minimum stay
                                                  • 5 BR,
                                                  • 5 BA,
                                                  • Sleeps 12
                                                    Book it Now!
                                                    3 night minimum stay
                                                    • 6 BR,
                                                    • 4 BA,
                                                    • Sleeps 12
                                                      Book it Now!
                                                      3 night minimum stay
                                                      • 6 BR,
                                                      • 4 BA,
                                                      • Sleeps 12
                                                        Book it Now!
                                                        3 night minimum stay
                                                        • 6 BR,
                                                        • 4 BA,
                                                        • Sleeps 14
                                                          Book it Now!
                                                          3 night minimum stay
                                                          • 6 BR,
                                                          • 4 BA,
                                                          • Sleeps 14
                                                            Book it Now!
                                                            3 night minimum stay
                                                            • 5 BR,
                                                            • 5 BA,
                                                            • Sleeps 12
                                                              Advertisement
                                                               

                                                              Recent Windsor Hills Reviews

                                                              Great Location and Nice Resort

                                                              5 of 5
                                                              We stayed here (two families with seven children) for one week in early September and had a fantastic time. The house is nicely furnished and very clean. The location is great. A mile off of 192, next to restaurants and shops and close to Disney World. The resort is very well kept and has a pool (with a slide), restaurant, playground, and other amenities. Sandy (the owner) was very friendly and accommodating. I highly recommend this house!
                                                              • Submitted: Sep 12, 2014
                                                              • Stayed: Aug 2014

                                                              Wonderful Villa - Home from Home

                                                              5 of 5
                                                              What an amazing Villa! Tiffany's Treasure is just perfect. We stayed there for 2 weeks in July and there were 11 of us in total - 3 families consisting of 6 adults, a teenager and 4 toddler/young children. We had been to Orlando before but never stayed in a villa. Now we will never choose anywhere else. The location is fantastic as there are lots of restaurants and shops within a 5 minute drive (if that) We didn't use the on site facilities at Windsor Hills but they were very good. The Villa is within easy access of the Disney estate and the I4 for access to Universal, International Drive and the outlet malls as well as other destinations. The security was very good at Windsor Hills and made us feel very secure during our stay. The villa has everything you need and really is a home from home. It is very spacious and you won't want for anything. Plenty of linen is provided (including pool towels) and the washing machine makes it easy to keep everything regularly clean. There is every kitchen utensil you can imagine and each bathroom has its own hair dryer. There is plenty of storage space and although we didn't use it due to time restraints with the parks, the games room had great equipment. The villa is very clean and well kept. It is also modern and very comfortable. The bedrooms are spacious and the themes of children's bedrooms are great. We travelled with 2 almost 2 year olds and the children's bedrooms are located very close to the main bedrooms so it was easy to listen out for them during the night. We contacted the management company before we travelled and were able to rent a crib from them at a reasonable price. The children loved the pool and travelling from the UK we had no idea about the Florida State Laws regarding the pools and so we were a bit concerned about the safety of it but there is a great mesh fence around the pool and an alarm on the doors leading to the area and so we had no concerns about the children at all whilst we were there. It was really easy to contact the owner and the management company both before and during our stay and they were very helpful. We will definitely stay here if we travel again as a large group and have already recommended the villa to many friends and family members. We cannot recommend this villa enough it was simply perfect and we wish it was ours so that we could stay there all the time! Thanks again to Maurice and the team for such a wonderful place to stay!
                                                              • Submitted: Aug 24, 2014
                                                              • Stayed: Jul 2014

                                                              Beautiful Orlando Vacation Home

                                                              5 of 5
                                                              This is a gorgeous home. The home met all of our expectations and I would HIGHLY recommend this home as a place to consider for your upcoming Kissimmee/Orlando visit. The home is located in a wonderful, well manicured, gated community. The driving distance to the entrance of the parks is about 2 miles from where the home is located in the Windsor Hills complex. The owners are a pleasure to work with. The owners contacted me several times during our two week visit to their home. The listing on this property is very accurate and this home looks and feels almost new. I would highly recommend this property. The two childrens bedrooms were wonderful for our grandchildren and the playroom that is setup in the garage is really and extra feature for this property that other homes in this area do not have. Our trip was mainly to this area to be able to take our grandchildren, son, and daughter in law to visit all the parks that attract so many people to this area. We plan on returning to this area in the future and I hope this home will be available again on our return trip.
                                                              • Submitted: Aug 23, 2014
                                                              • Stayed: Aug 2014