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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
    (13 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 4
    House #450575vb
    13
    Viewed 20 times in the last 48 hours
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      • 2 BR
      • 1 BA
      • Sleeps 4
      Bungalow #780146vb
      4
      Viewed 8 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 15 times in the last 48 hours
          Wonderful! 4.8/5
          (53 reviews)
          avg/night
          • 3 BR
          • 3 BA
          • Sleeps 10
          House #981770
          53
          Viewed 43 times in the last 48 hours
            Excellent! 4.5/5
            (19 reviews)
            avg/night
            • 2 BR
            • 1 BA
            • Sleeps 3
            Bungalow #3993910
            19
            Viewed 13 times in the last 48 hours
              Excellent! 4.7/5
              (24 reviews)
              avg/night
              • 2 BR
              • 2 BA
              • Sleeps 5
              Bungalow #322808vb
              24
              Viewed 5 times in the last 48 hours
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                • 2 BR
                • 1 BA
                • Sleeps 5
                Cottage #919138vb
                2
                Viewed 6 times in the last 48 hours
                  Exceptional! 5/5
                  (6 reviews)
                  avg/night
                  • 4 BR
                  • 3 BA
                  • Separate Toilet
                  • Sleeps 8
                  House #885924vb
                  6
                  Viewed 19 times in the last 48 hours
                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                    Apartment #683231vb
                    7
                      Exceptional! 5/5
                      (10 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Separate Toilet
                      • Sleeps 6
                      House #823160vb
                      10
                      Viewed 33 times in the last 48 hours
                        Excellent! 4.6/5
                        (31 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 9
                        House #929474
                        31
                        Viewed 91 times in the last 48 hours
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          House #1069947vb
                          Viewed 7 times in the last 48 hours
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                            • 2 BR
                            • 2 BA
                            • Sleeps 4
                            House #1027239vb
                            Viewed 6 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 21 times in the last 48 hours
                                Wonderful! 4.8/5
                                (21 reviews)
                                avg/night
                                • 4 BR
                                • 2 BA
                                • Sleeps 10
                                House #3023348
                                21
                                Viewed 25 times in the last 48 hours
                                  Exceptional! 5/5
                                  (20 reviews)
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 4
                                  Cottage #669117vb
                                  20
                                  Viewed 5 times in the last 48 hours
                                    Exceptional! 5/5
                                    (28 reviews)
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    Studio #493118vb
                                    28
                                    Viewed 20 times in the last 48 hours
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 8
                                      House #990123vb
                                      3
                                      Viewed 5 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (4 reviews)
                                        avg/night
                                        • 3 BR
                                        • 3 BA
                                        • Sleeps 8
                                        House #901305vb
                                        4
                                        Viewed 13 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (11 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          House #243102
                                          11
                                          Viewed 6 times in the last 48 hours
                                            avg/night
                                            • 3 BR
                                            • 2 BA
                                            • Separate Toilet
                                            • Sleeps 6
                                            House #4303470
                                            6
                                            Viewed 25 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (6 reviews)
                                              avg/night
                                              • 3 BR
                                              • 1 BA
                                              • Sleeps 7
                                              House #3166620
                                              6
                                              Viewed 14 times in the last 48 hours
                                                Exceptional! 5/5
                                                (12 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 8
                                                House #3023034
                                                12
                                                Viewed 7 times in the last 48 hours
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 7
                                                  House #1030436vb
                                                  1
                                                  Viewed 7 times in the last 48 hours
                                                    Excellent! 4.7/5
                                                    (7 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                    Studio #4245895
                                                    7
                                                    Viewed 22 times in the last 48 hours
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                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      Apartment #1069352vb
                                                      Viewed 6 times in the last 48 hours
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                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        House #1097929vb
                                                        Viewed 19 times in the last 48 hours
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          Apartment #1046545vb
                                                          Viewed 8 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
                                                              • 4 BR
                                                              • 2 BA
                                                              • Sleeps 10
                                                              House #694235vb
                                                              Viewed 18 times in the last 48 hours
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 4
                                                                House #1060352vb
                                                                Viewed 16 times in the last 48 hours
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  House #1114835vb
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    House #1129469vb
                                                                    Viewed 5 times in the last 48 hours
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 2
                                                                      House #1091039vb
                                                                      Viewed 7 times in the last 48 hours
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 2
                                                                        House #4628707
                                                                        Viewed 5 times in the last 48 hours
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2
                                                                          House #1114504vb
                                                                          Viewed 12 times in the last 48 hours
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Condo #1127343vb
                                                                            Viewed 10 times in the last 48 hours
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              House #1114809vb
                                                                              Viewed 10 times in the last 48 hours
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 6
                                                                                Condo #4626354
                                                                                Viewed 21 times in the last 48 hours
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Condo #724660vb
                                                                                  2
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 2
                                                                                    House #1114391vb
                                                                                    Viewed 14 times in the last 48 hours
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      House #1056448vb
                                                                                      Viewed 20 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (10 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        House #319653vb
                                                                                        10
                                                                                        Viewed 13 times in the last 48 hours
                                                                                          Exceptional! 5/5
                                                                                          (9 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          House #338205vb
                                                                                          9
                                                                                          Viewed 10 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (134 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Hotel #3905183
                                                                                            134
                                                                                            Viewed 673 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (9 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              House #792993vb
                                                                                              9
                                                                                              Viewed 97 times in the last 48 hours
                                                                                                Excellent! 4.7/5
                                                                                                (40 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 10
                                                                                                Condo #4141115
                                                                                                40
                                                                                                Viewed 481 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (45 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  Condo #512028vb
                                                                                                  45
                                                                                                  Viewed 219 times in the last 48 hours
                                                                                                    Excellent! 4.6/5
                                                                                                    (28 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    Condo #746426vb
                                                                                                    28
                                                                                                    Viewed 180 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (66 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 10
                                                                                                      Villa #34854vb
                                                                                                      66
                                                                                                      Viewed 509 times in the last 48 hours

                                                                                                      Winter Park Holiday Rentals & Homes (300+)