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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.

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Winter Park Holiday Rentals & Homes (300+)

  • 1 - 50 of 300+
Additional service fee may apply.
    Excellent! 4.7/5
    (7 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 3
    House #709825vb
    7
    Viewed 11 times in the last 48 hours
      • 3 BR
      • 2 BA
      • Sleeps 6
      House #243102
      10
        Exceptional! 5.0/5
        (10 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Separate Toilets
        • Sleeps 8
        House #3023034
        10
        Viewed 20 times in the last 48 hours
          Exceptional! 5.0/5
          (13 reviews)
          avg/night
          • 3 BR
          • 2 BA
          • Sleeps 5
          House #466067vb
          13
          Viewed 9 times in the last 48 hours
            Exceptional! 5.0/5
            (17 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 4
            Cottage #669117vb
            17
            Viewed 12 times in the last 48 hours
              Exceptional! 5.0/5
              (11 reviews)
              avg/night
              • 1 BR
              • 1 BA
              • Separate Toilet
              • Sleeps 2
              Bungalow #444585vb
              11
              Viewed 15 times in the last 48 hours
                Wonderful! 4.9/5
                (11 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Separate Toilet
                • Sleeps 8
                House #367326vb
                11
                Viewed 8 times in the last 48 hours
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 5
                  Cottage #919138vb
                  1 Review
                  Viewed 22 times in the last 48 hours
                    • 4 BR
                    • 3 BA
                    • Separate Toilet
                    • Sleeps 8
                    House #885924vb
                    Viewed 14 times in the last 48 hours
                      Exceptional! 5.0/5
                      (11 reviews)
                      avg/night
                      • 4 BR
                      • 2 BA
                      • Separate Toilet
                      • Sleeps 8
                      House #3670851
                      11
                      Viewed 10 times in the last 48 hours
                        • 3 BR
                        • 3 BA
                        • Sleeps 8
                        House #901305vb
                        1 Review
                        Viewed 6 times in the last 48 hours
                          Exceptional! 5.0/5
                          (24 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          Studio #493118vb
                          24
                          Viewed 5 times in the last 48 hours
                            Excellent! 4.7/5
                            (44 reviews)
                            avg/night
                            • 3 BR
                            • 3 BA
                            • Sleeps 10
                            House #981770
                            44
                            Viewed 17 times in the last 48 hours
                              Wonderful! 4.8/5
                              (21 reviews)
                              avg/night
                              • 3 BR
                              • 3 BA
                              • Sleeps 10
                              House #943873
                              21
                              Viewed 7 times in the last 48 hours
                                Exceptional! 5.0/5
                                (6 reviews)
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Separate Toilet
                                • Sleeps 6
                                House #823160vb
                                6
                                Viewed 33 times in the last 48 hours
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 5
                                  Bungalow #322808vb
                                  20
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    Apartment #683231vb
                                    4
                                    Viewed 10 times in the last 48 hours
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 9
                                      House #929474
                                      22
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Bungalow #780146vb
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          House #338205vb
                                          9
                                            Excellent! 4.3/5
                                            (9 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 3
                                            Bungalow #3993910
                                            9
                                            Viewed 18 times in the last 48 hours
                                              • 3 BR
                                              • 3 BA
                                              • Sleeps 6
                                              House #502419vb
                                              10
                                                Wonderful! 4.8/5
                                                (11 reviews)
                                                avg/night
                                                • 4 BR
                                                • 2 BA
                                                • Sleeps 10
                                                House #3023348
                                                11
                                                Viewed 28 times in the last 48 hours
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 5
                                                  House #952054vb
                                                  Viewed 12 times in the last 48 hours
                                                    Excellent! 4.5/5
                                                    (10 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 4
                                                    House #450575vb
                                                    10
                                                    Viewed 6 times in the last 48 hours
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 2
                                                      Studio #4245895
                                                      3
                                                      Viewed 10 times in the last 48 hours
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Condo #724660vb
                                                        1 Review
                                                          Wonderful! 4.8/5
                                                          (6 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 1 BA
                                                          • Sleeps 7
                                                          House #3166620
                                                          6
                                                          Viewed 8 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (13 reviews)
                                                            avg/night
                                                            • 4 BR
                                                            • 4 BA
                                                            • Sleeps 8
                                                            Villa #305144vb
                                                            13
                                                            Viewed 15 times in the last 48 hours
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Separate Toilet
                                                              • Sleeps 6
                                                              House #4303470
                                                              2 Reviews
                                                              Viewed 40 times in the last 48 hours
                                                                • 3 BR
                                                                • 3 BA
                                                                • Sleeps 6
                                                                House #869308vb
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  Apartment #4351693
                                                                  Viewed 7 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (10 reviews)
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    House #319653vb
                                                                    10
                                                                    Viewed 5 times in the last 48 hours
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      Townhome #905084vb
                                                                      Viewed 19 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (21 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        House #514103vb
                                                                        21
                                                                        Viewed 9 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (12 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 10
                                                                          House #787925vb
                                                                          12
                                                                          Viewed 8 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (19 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Separate Toilet
                                                                            • Sleeps 6
                                                                            Townhome #3763171
                                                                            19
                                                                            Viewed 13 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (8 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              House #802507vb
                                                                              8
                                                                              Viewed 12 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (25 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 5
                                                                                Bungalow #367651vb
                                                                                25
                                                                                Viewed 24 times in the last 48 hours
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                  House #3569183
                                                                                  38
                                                                                    Wonderful! 4.8/5
                                                                                    (6 reviews)
                                                                                    avg/night
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 3
                                                                                    Cottage #490078vb
                                                                                    6
                                                                                    Viewed 14 times in the last 48 hours
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 5
                                                                                      House #3697726
                                                                                      4
                                                                                      Viewed 12 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (6 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 2
                                                                                        Studio #869623vb
                                                                                        6
                                                                                        Viewed 25 times in the last 48 hours
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                          Cottage #769712vb
                                                                                          2 Reviews
                                                                                          Viewed 47 times in the last 48 hours
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 6
                                                                                            House #907712vb
                                                                                            3
                                                                                            Viewed 56 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (8 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              House #4040125
                                                                                              8
                                                                                              Viewed 48 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (9 reviews)
                                                                                                avg/night
                                                                                                • 6 BR
                                                                                                • 5 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 15
                                                                                                Villa #393643vb
                                                                                                9
                                                                                                Viewed 30 times in the last 48 hours
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 5
                                                                                                  Bungalow #4236191
                                                                                                  1 Review
                                                                                                  Viewed 16 times in the last 48 hours
                                                                                                    Excellent! 4.6/5
                                                                                                    (8 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 9
                                                                                                    House #762584vb
                                                                                                    8
                                                                                                    Viewed 17 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (8 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Bungalow #4031187
                                                                                                      8
                                                                                                      • 1 - 50 of 300+