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Make a holiday apartment in Winter Park your home away from home

Located in a leafy suburb of Orlando, a Winter Park holiday apartment or villa is an ideal base for enjoying everything the metropolitan area has to offer, while providing a scenic and serene retreat from the hustle and bustle in the evenings. Planned and developed as a resort town at the turn of the 20th century, the brick-cobbled streets surrounding the rentals in Winter Park encourage strolling and browsing; perhaps stopping for a meal in one of the many upscale restaurants. With a wide range of villas, apartments, cabins and lodges to choose from, HomeAway offers Winter Park holiday accommodation to suit every taste.

Things to do

-Festivals: The annual Bach Festival is held every autumn at Winter Park's Rollins College Campus; a must if tourists have a passion for choral and classical music. March's Sidewalk Art Festival is one of the country's most prestigious, as is November's Winter Park Concours d'Elegance, for lovers of combustion-powered artistry of the four-wheeled variety.

-Gardens: Mead Botanical Garden encompasses 47 acres of parkland, and is typically within walking distance of most Winter Park holiday rentals. It boasts a number of ecosystems to explore by foot on the boardwalk, or by bicycle on the bike trails. A 300 seater amphitheatre also anchors this urban oasis, along with a discovery barn, butterfly garden and a recreation centre.

-History: Many of the buildings surrounding rentals in Winter Park are over 100 years old, which is a real rarity in the US with their propensity for constant urban renewal. They shoulder tree-shaded and brick-cobbled streets, and abut the Venetian canals, blending elegantly with picturesque lakes and meticulous parks.

-Theme Parks: While Winter Park holiday rentals are sited in a peaceful, quaint town, Orlando has some of the most exciting theme parks in the world. From behemoths like Disney World, Universal Studios and Sea World, to smaller parks like Legoland, the Kennedy Space Centre Visitor Complex, the Holy Land Experience and Gatorland, tourists can easily do a theme park a day!

-Nightlife: Eating out is typically quite high end in Winter Park, matching the atmosphere of this quaint and elegant town. From French bistros to tapas bars, BBQ joints to fusion fare, there's a venue for every taste and budget, but the tendency is towards fine dining. Bars and nightclubs are equally cosmopolitan.

Weather in Winter Park

Winter Park has a typical Florida subtropical climate, with warm, dry winters and long, hot summers, encouraging the eponymous notion of the town as a winter destination. Rain falls mainly during the summer as heavy thunderstorms, breaking the humidity and also helping to keep things cooler than inland areas further north. Temperatures from June to September top out at around the mid-30°C mark, while winter maximums hover around 22°C: it’s about the same as a British summer.

Travel to Winter Park

Travel to Winter Park is a cinch as Orlando International Airport is only 14 miles away. Unusually for Florida, visitors could feasibly get around on Orlando's public transport. This is often undesirable, however, especially during the summer with the heat, humidity, and frequent cloudbursts. Fly/drive is still preferable, despite Orlando's extensive public transport system. There is an Amtrak station in Winter Park itself, if guests fancy an iconic American train journey, though Amtrak is a national network rather than a local one.

    Excellent! 4.6/5
    (12 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 4
    House #450575vb
    12
    Viewed 30 times in the last 48 hours
      Wonderful! 4.8/5
      (52 reviews)
      avg/night
      • 3 BR
      • 3 BA
      • Sleeps 10
      House #981770
      52
      Viewed 47 times in the last 48 hours
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 4
        Bungalow #780146vb
        4
        Viewed 31 times in the last 48 hours
          Exceptional! 5/5
          (15 reviews)
          avg/night
          • 1 BR
          • 1 BA
          • Separate Toilet
          • Sleeps 2
          Bungalow #444585vb
          15
          Viewed 17 times in the last 48 hours
            Excellent! 4.5/5
            (15 reviews)
            avg/night
            • 2 BR
            • 1 BA
            • Sleeps 3
            Bungalow #3993910
            15
            Viewed 26 times in the last 48 hours
              • 4 BR
              • 3 BA
              • Separate Toilet
              • Sleeps 8
              House #885924vb
              4
              Viewed 21 times in the last 48 hours
                • 2 BR
                • 1 BA
                • Sleeps 5
                Cottage #919138vb
                2
                  Excellent! 4.7/5
                  (24 reviews)
                  avg/night
                  • 2 BR
                  • 2 BA
                  • Sleeps 5
                  Bungalow #322808vb
                  24
                  Viewed 12 times in the last 48 hours
                    Excellent! 4.6/5
                    (31 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 9
                    House #929474
                    31
                    Viewed 49 times in the last 48 hours
                      Wonderful! 4.9/5
                      (7 reviews)
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Sleeps 2
                      Apartment #683231vb
                      7
                      Viewed 5 times in the last 48 hours
                        Exceptional! 5/5
                        (10 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Separate Toilet
                        • Sleeps 6
                        House #823160vb
                        10
                        Viewed 39 times in the last 48 hours
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          House #1069947vb
                          Viewed 8 times in the last 48 hours
                            Wonderful! 4.8/5
                            (21 reviews)
                            avg/night
                            • 4 BR
                            • 2 BA
                            • Sleeps 10
                            House #3023348
                            21
                            Viewed 19 times in the last 48 hours
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              House #1027239vb
                              Viewed 8 times in the last 48 hours
                                Exceptional! 5/5
                                (20 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 4
                                Cottage #669117vb
                                20
                                Viewed 20 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (30 reviews)
                                  avg/night
                                  • 3 BR
                                  • 3 BA
                                  • Separate Toilet
                                  • Sleeps 9
                                  House #929471
                                  30
                                  Viewed 22 times in the last 48 hours
                                    Exceptional! 5/5
                                    (28 reviews)
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    Studio #493118vb
                                    28
                                    Viewed 5 times in the last 48 hours
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 8
                                      House #990123vb
                                      2
                                      Viewed 18 times in the last 48 hours
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 5
                                        House #952054vb
                                        3
                                        Viewed 28 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (11 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          House #243102
                                          11
                                          Viewed 14 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (6 reviews)
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 2
                                            Studio #4245895
                                            6
                                            Viewed 27 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (4 reviews)
                                              avg/night
                                              • 3 BR
                                              • 3 BA
                                              • Sleeps 8
                                              House #901305vb
                                              4
                                              Viewed 7 times in the last 48 hours
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Separate Toilet
                                                • Sleeps 6
                                                House #4303470
                                                6
                                                Viewed 48 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (6 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 1 BA
                                                  • Sleeps 7
                                                  House #3166620
                                                  6
                                                  Viewed 21 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (12 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    House #3023034
                                                    12
                                                    Viewed 15 times in the last 48 hours
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 7
                                                      House #1030436vb
                                                      Viewed 8 times in the last 48 hours
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                        Apartment #1069352vb
                                                        Viewed 26 times in the last 48 hours
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          Apartment #1046545vb
                                                          Viewed 32 times in the last 48 hours
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Guest House #1033184vb
                                                            Viewed 5 times in the last 48 hours
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Condo #724660vb
                                                              2
                                                              Viewed 7 times in the last 48 hours
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 2
                                                                House #1091039vb
                                                                Viewed 10 times in the last 48 hours
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 4
                                                                  House #1060352vb
                                                                  Viewed 15 times in the last 48 hours
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    House #1097929vb
                                                                    Viewed 18 times in the last 48 hours
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      House #1056448vb
                                                                      Viewed 15 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (10 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        House #319653vb
                                                                        10
                                                                        Viewed 7 times in the last 48 hours
                                                                          Exceptional! 5/5
                                                                          (9 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          House #338205vb
                                                                          9
                                                                          Viewed 7 times in the last 48 hours
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Sleeps 10
                                                                            House #694235vb
                                                                            Viewed 19 times in the last 48 hours
                                                                              Excellent! 4.7/5
                                                                              (125 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Hotel #3905183
                                                                              125
                                                                              Viewed 584 times in the last 48 hours
                                                                                Excellent! 4.6/5
                                                                                (37 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 10
                                                                                Condo #4141115
                                                                                37
                                                                                Viewed 311 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (9 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  House #792993vb
                                                                                  9
                                                                                  Viewed 61 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (66 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 10
                                                                                    Villa #34854vb
                                                                                    66
                                                                                    Viewed 354 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (89 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                      Condo #964487
                                                                                      89
                                                                                      Viewed 127 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (45 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        House #3569183
                                                                                        45
                                                                                        Viewed 10 times in the last 48 hours
                                                                                          Very Good! 4/5
                                                                                          (15 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          House #507153vb
                                                                                          15
                                                                                          Viewed 51 times in the last 48 hours
                                                                                            Excellent! 4.6/5
                                                                                            (53 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 9
                                                                                            Villa #56513
                                                                                            53
                                                                                            Viewed 66 times in the last 48 hours
                                                                                              Very Good! 4.1/5
                                                                                              (34 reviews)
                                                                                              avg/night
                                                                                              • Studio
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Studio #911234vb
                                                                                              34
                                                                                              Viewed 210 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (34 reviews)
                                                                                                avg/night
                                                                                                • 5 BR
                                                                                                • 5 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 10
                                                                                                Villa #331193
                                                                                                34
                                                                                                Viewed 327 times in the last 48 hours
                                                                                                  Excellent! 4.6/5
                                                                                                  (93 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Hotel #3905184
                                                                                                  93
                                                                                                  Viewed 306 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (12 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    Apartment #766809vb
                                                                                                    12
                                                                                                    Viewed 18 times in the last 48 hours
                                                                                                      Excellent! 4.5/5
                                                                                                      (48 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 8
                                                                                                      Villa #164801
                                                                                                      48
                                                                                                      Viewed 169 times in the last 48 hours

                                                                                                      Winter Park Holiday Rentals & Homes (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      So glad to have chosen to stay here

                                                                                                      5 of 5
                                                                                                      I stayed here for two weeks in April 2011 having travelled from England with my daughter and my parents. I really do have nothing but good things to say about it and would recommend it to anybody looking for a quality property near to Disneyland. The villa is very well proportioned and well maintained, and has all the comforts of home including appliances, wireless internet and three TVs (one with DVD player) and even an iPod dock. The kitchen has good storage and plentiful crockery, utensils etc. The master bedroom is impressive as is the en suite and dressing room, and the other three bedrooms and two bathrooms are more than adequate for adults or children to use. The pool was clean and warm (even though we chose not to heat it). I loved the little details like board games, DVDs and books for the children, plentiful towels, instructions for all the appliances and the folder of local information. The development which the villa is on is quiet, but not so quiet that you can't enjoy yourself. The clubhouse was a great amenity that provides services such as ticket and newspaper sales and dvd rentals as well as the pool, gym etc. They also put on events such as an Easter Egg Hunt which my daughter loved, and a cook out. The owner of the property was extremely efficient, answered all queries etc very quickly and thoroughly and also provided local information that proved very useful to us. There is also a local management contact that you can call if you have any issues - I called them when I was unable to operate the washing machine (due to my own stupidity!) and they came round quickly to help. The villa is about 20 minutes drive to Disney, 45 minutes from the airport and is close to local shops and restaurants. This was the first time I have used the internet to choose a privately owned property and I was nervous about it. However, when I arrived I was relieved to discover that the nerves had been unneccesary, and I had chosen very well. If you are looking for a property to rent, you would do well to choose this one.
                                                                                                      • Review Submitted: May 01, 2011
                                                                                                      • Date of Stay: Apr 2011

                                                                                                      One Week Getaway

                                                                                                      5 of 5
                                                                                                      The physical location (about 20-25 minutes from Universal) was not our first choice, but in the end, it was really our only choice. The house, the land, the lake made for the perfect combination of peace and quiet that we ultimately sought out. After a long day at the parks, returning to the house was something we looked forward to... take a dip, lounge in the wonderfully manicured backyard, grill on the back porch. RInse, wash, repeat... we found ourselves in this pattern almost everyday. Despite the owners being in the UK, they were extremely attentive when a minor glitch popped up. Rest assured they have locals taking great care to ensure that all our needs were met and in a timely fashion. If your kids need to see Mickey every waking moment of every day, then by all means stay on site at Disney, but if you would also like to enjoy YOUR vacation, this is not a treat to miss out on.
                                                                                                      • Review Submitted: Feb 04, 2010
                                                                                                      • Date of Stay: Jan 2010