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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 8 times in the last 48 hours
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 4
      Bungalow #780146vb
      4
      Viewed 10 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 11 times in the last 48 hours
          Wonderful! 4.8/5
          (53 reviews)
          avg/night
          • 3 BR
          • 3 BA
          • Sleeps 10
          House #981770
          53
          Viewed 26 times in the last 48 hours
            Excellent! 4.5/5
            (19 reviews)
            avg/night
            • 2 BR
            • 1 BA
            • Sleeps 3
            Bungalow #3993910
            19
            Viewed 18 times in the last 48 hours
              • 2 BR
              • 2 BA
              • Sleeps 5
              Bungalow #322808vb
              24
                • 2 BR
                • 1 BA
                • Sleeps 5
                Cottage #919138vb
                2
                  Exceptional! 5/5
                  (6 reviews)
                  avg/night
                  • 4 BR
                  • 3 BA
                  • Separate Toilet
                  • Sleeps 8
                  House #885924vb
                  6
                  Viewed 7 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 19 times in the last 48 hours
                        Excellent! 4.6/5
                        (31 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 9
                        House #929474
                        31
                        Viewed 32 times in the last 48 hours
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          House #1069947vb
                          Viewed 6 times in the last 48 hours
                            avg/night
                            • 2 BR
                            • 2 BA
                            • Sleeps 4
                            House #1027239vb
                            Viewed 5 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 7 times in the last 48 hours
                                Wonderful! 4.8/5
                                (21 reviews)
                                avg/night
                                • 4 BR
                                • 2 BA
                                • Sleeps 10
                                House #3023348
                                21
                                Viewed 14 times in the last 48 hours
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 4
                                  Cottage #669117vb
                                  20
                                    Exceptional! 5/5
                                    (28 reviews)
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    Studio #493118vb
                                    28
                                    Viewed 10 times in the last 48 hours
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 8
                                      House #990123vb
                                      3
                                      Viewed 8 times in the last 48 hours
                                        • 3 BR
                                        • 3 BA
                                        • Sleeps 8
                                        House #901305vb
                                        4
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          House #243102
                                          11
                                            avg/night
                                            • 3 BR
                                            • 2 BA
                                            • Separate Toilet
                                            • Sleeps 6
                                            House #4303470
                                            6
                                            Viewed 26 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (6 reviews)
                                              avg/night
                                              • 3 BR
                                              • 1 BA
                                              • Sleeps 7
                                              House #3166620
                                              6
                                                Exceptional! 5/5
                                                (12 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 8
                                                House #3023034
                                                12
                                                Viewed 8 times in the last 48 hours
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 7
                                                  House #1030436vb
                                                  1
                                                  Viewed 8 times in the last 48 hours
                                                    Excellent! 4.7/5
                                                    (7 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                    Studio #4245895
                                                    7
                                                    Viewed 16 times in the last 48 hours
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      Apartment #1069352vb
                                                        avg/night
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        House #1097929vb
                                                        Viewed 11 times in the last 48 hours
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          Apartment #1046545vb
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Guest House #1033184vb
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 4
                                                              House #1060352vb
                                                                • 4 BR
                                                                • 2 BA
                                                                • Sleeps 10
                                                                House #694235vb
                                                                Viewed 14 times in the last 48 hours
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  House #1129469vb
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    House #1114835vb
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 2
                                                                      House #1091039vb
                                                                      Viewed 5 times in the last 48 hours
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Condo #1127343vb
                                                                        Viewed 9 times in the last 48 hours
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2
                                                                          House #4628707
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                            Condo #4626354
                                                                            Viewed 11 times in the last 48 hours
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                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              House #1114809vb
                                                                              Viewed 8 times in the last 48 hours
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 2
                                                                                House #1114504vb
                                                                                Viewed 24 times in the last 48 hours
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Condo #724660vb
                                                                                  2
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    House #1056448vb
                                                                                    Viewed 22 times in the last 48 hours
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 2
                                                                                      House #1114391vb
                                                                                      Viewed 11 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (10 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        House #319653vb
                                                                                        10
                                                                                        Viewed 8 times in the last 48 hours
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          House #338205vb
                                                                                          9
                                                                                            Excellent! 4.7/5
                                                                                            (133 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Hotel #3905183
                                                                                            133
                                                                                            Viewed 171 times in the last 48 hours
                                                                                              Excellent! 4.7/5
                                                                                              (39 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 10
                                                                                              Condo #4141115
                                                                                              39
                                                                                              Viewed 282 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (9 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                House #792993vb
                                                                                                9
                                                                                                Viewed 49 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (45 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  Condo #512028vb
                                                                                                  45
                                                                                                  Viewed 113 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (91 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    Condo #964487
                                                                                                    91
                                                                                                    Viewed 115 times in the last 48 hours
                                                                                                      Excellent! 4.6/5
                                                                                                      (28 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 8
                                                                                                      Condo #746426vb
                                                                                                      28
                                                                                                      Viewed 105 times in the last 48 hours

                                                                                                      Winter Park Holiday Rentals & Homes (300+)