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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.

Additional service fee may apply.
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    Excellent! 4.6/5
    (8 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 3
    House #709825vb
    8
    Viewed 76 times in the last 48 hours
      • 3 BR
      • 2 BA
      • Sleeps 6
      Condo #724660vb
      1
      Viewed 24 times in the last 48 hours
        Wonderful! 4.9/5
        (11 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 6
        House #243102
        11
        Viewed 47 times in the last 48 hours
          Exceptional! 5/5
          (14 reviews)
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          • 3 BR
          • 2 BA
          • Sleeps 5
          House #466067vb
          14
          Viewed 86 times in the last 48 hours
            Excellent! 4.7/5
            (47 reviews)
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            • 3 BR
            • 3 BA
            • Sleeps 10
            House #981770
            47
            Viewed 76 times in the last 48 hours
              Excellent! 4.5/5
              (10 reviews)
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              • 2 BR
              • 2 BA
              • Sleeps 4
              House #450575vb
              10
              Viewed 45 times in the last 48 hours
                Exceptional! 5/5
                (17 reviews)
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                • 2 BR
                • 2 BA
                • Sleeps 4
                Cottage #669117vb
                17
                Viewed 38 times in the last 48 hours
                  Exceptional! 5/5
                  (11 reviews)
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                  • 4 BR
                  • 2 BA
                  • Separate Toilet
                  • Sleeps 8
                  House #3670851
                  11
                  Viewed 33 times in the last 48 hours
                    Exceptional! 5/5
                    (11 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Separate Toilet
                    • Sleeps 2
                    Bungalow #444585vb
                    11
                    Viewed 37 times in the last 48 hours
                      Excellent! 4.5/5
                      (11 reviews)
                      avg/night
                      • 2 BR
                      • 1 BA
                      • Sleeps 3
                      Bungalow #3993910
                      11
                      Viewed 99 times in the last 48 hours
                        Wonderful! 4.9/5
                        (14 reviews)
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                        • 4 BR
                        • 2 BA
                        • Sleeps 10
                        House #3023348
                        14
                        Viewed 46 times in the last 48 hours
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                          • 2 BR
                          • 1 BA
                          • Sleeps 4
                          Bungalow #780146vb
                          1
                          Viewed 43 times in the last 48 hours
                            Exceptional! 5/5
                            (7 reviews)
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                            • 3 BR
                            • 2 BA
                            • Separate Toilet
                            • Sleeps 6
                            House #823160vb
                            7
                            Viewed 69 times in the last 48 hours
                              Wonderful! 4.8/5
                              (13 reviews)
                              avg/night
                              • 3 BR
                              • 2 BA
                              • Separate Toilet
                              • Sleeps 8
                              House #367326vb
                              13
                              Viewed 137 times in the last 48 hours
                                Excellent! 4.7/5
                                (24 reviews)
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                                • 3 BR
                                • 2 BA
                                • Sleeps 9
                                House #929474
                                24
                                Viewed 47 times in the last 48 hours
                                  • 4 BR
                                  • 3 BA
                                  • Separate Toilet
                                  • Sleeps 8
                                  House #885924vb
                                  2
                                  Viewed 32 times in the last 48 hours
                                    Wonderful! 4.8/5
                                    (5 reviews)
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                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    Apartment #683231vb
                                    5
                                    Viewed 19 times in the last 48 hours
                                      Excellent! 4.7/5
                                      (22 reviews)
                                      avg/night
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 5
                                      Bungalow #322808vb
                                      22
                                      Viewed 6 times in the last 48 hours
                                        Exceptional! 5/5
                                        (26 reviews)
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                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 2
                                        Studio #493118vb
                                        26
                                        Viewed 36 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (27 reviews)
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                                          • 3 BR
                                          • 3 BA
                                          • Separate Toilet
                                          • Sleeps 9
                                          House #929471
                                          27
                                          Viewed 20 times in the last 48 hours
                                            Very Good! 4/5
                                            (10 reviews)
                                            View details for price
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 6
                                            House #502419vb
                                            10
                                            Viewed 5 times in the last 48 hours
                                              avg/night
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 5
                                              Cottage #919138vb
                                              1
                                              Viewed 20 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (6 reviews)
                                                avg/night
                                                • 3 BR
                                                • 1 BA
                                                • Sleeps 7
                                                House #3166620
                                                6
                                                Viewed 17 times in the last 48 hours
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                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  House #990123vb
                                                  Viewed 19 times in the last 48 hours
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                    Studio #4245895
                                                    3
                                                    Viewed 25 times in the last 48 hours
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • Separate Toilet
                                                      • Sleeps 6
                                                      House #4303470
                                                      4
                                                      Viewed 63 times in the last 48 hours
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 10
                                                        House #985828
                                                        Viewed 41 times in the last 48 hours
                                                          Excellent! 4.5/5
                                                          (2 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 8
                                                          House #901305vb
                                                          2
                                                          Viewed 9 times in the last 48 hours
                                                            Exceptional! 5/5
                                                            (13 reviews)
                                                            avg/night
                                                            • 4 BR
                                                            • 4 BA
                                                            • Sleeps 8
                                                            Villa #305144vb
                                                            13
                                                            Viewed 44 times in the last 48 hours
                                                              Exceptional! 5/5
                                                              (10 reviews)
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                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              House #3023034
                                                              10
                                                              Viewed 18 times in the last 48 hours
                                                                Exceptional! 5/5
                                                                (9 reviews)
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                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                House #338205vb
                                                                9
                                                                Viewed 12 times in the last 48 hours
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                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • Sleeps 6
                                                                  House #869308vb
                                                                  Viewed 12 times in the last 48 hours
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 10
                                                                    House #694235vb
                                                                    Viewed 28 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (10 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      House #319653vb
                                                                      10
                                                                      Viewed 11 times in the last 48 hours
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Condo #809544vb
                                                                        1
                                                                        Viewed 122 times in the last 48 hours
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          Condo #809543vb
                                                                          3
                                                                          Viewed 107 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (25 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 10
                                                                            Condo #4141115
                                                                            25
                                                                            Viewed 276 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (87 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              Condo #964487
                                                                              87
                                                                              Viewed 93 times in the last 48 hours
                                                                                Excellent! 4.6/5
                                                                                (70 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Hotel #3905184
                                                                                70
                                                                                Viewed 453 times in the last 48 hours
                                                                                  Exceptional! 5/5
                                                                                  (20 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Villa #1869266
                                                                                  20
                                                                                  Viewed 100 times in the last 48 hours
                                                                                    Good! 3.9/5
                                                                                    (10 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    House #507153vb
                                                                                    10
                                                                                    Viewed 325 times in the last 48 hours
                                                                                      Exceptional! 5/5
                                                                                      (6 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 8
                                                                                      House #4069886
                                                                                      6
                                                                                      Viewed 58 times in the last 48 hours
                                                                                        Excellent! 4.7/5
                                                                                        (15 reviews)
                                                                                        avg/night
                                                                                        • 5 BR
                                                                                        • 2 BA
                                                                                        • Separate Toilet
                                                                                        • Sleeps 12
                                                                                        Villa #434457
                                                                                        15
                                                                                        Viewed 121 times in the last 48 hours
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 8
                                                                                          Multiple rentals Condo #407718
                                                                                          45
                                                                                          Viewed 119 times in the last 48 hours
                                                                                            Exceptional! 5/5
                                                                                            (39 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8
                                                                                            House #3569183
                                                                                            39
                                                                                            Viewed 17 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (29 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 10
                                                                                              House #4079570
                                                                                              29
                                                                                              Viewed 290 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (27 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 8
                                                                                                House #8063170
                                                                                                27
                                                                                                Viewed 94 times in the last 48 hours
                                                                                                  Excellent! 4.5/5
                                                                                                  (15 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 5
                                                                                                  Condo #3834010
                                                                                                  15
                                                                                                  Viewed 127 times in the last 48 hours
                                                                                                    Excellent! 4.7/5
                                                                                                    (48 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Separate Toilets
                                                                                                    • Sleeps 8
                                                                                                    Townhome #158585
                                                                                                    48
                                                                                                    Viewed 93 times in the last 48 hours
                                                                                                      Excellent! 4.6/5
                                                                                                      (66 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Condo #223334
                                                                                                      66
                                                                                                      Viewed 157 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Winter Park Holiday Rentals & Homes (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Perfect Holiday and Business Escape

                                                                                                      5 of 5
                                                                                                      We used two of the 3 condos available at the beginning of February for a company convention. Our large group was accommodated perfectly and the owner was prompt in all responses. We highly recommend all of these properties because they are clean and centrally located to everything in Orlando.
                                                                                                      • Review Submitted: 21-Feb-2017
                                                                                                      • Date of Stay: Jan 2017

                                                                                                      A wonderful location and a beautiful property

                                                                                                      5 of 5
                                                                                                      This is a really nice villa with a great eye to detail giving everything we needed for a great holiday. The four bedrooms are spacious and well furnished, as is the rest of the property. We have stayed in loads of villas all over Orlando in our 30+ years of holidaying there and this one is among the best we have been to. The swimming pool is a good size it is, importantly, very clean and well maintained, we have been to properties that have ruined our vacation due to a lack of pool maintainance, it is after all, an essential part of the Florida holiday experience. Being located a few hundred metres from Osceola Parkway it is really easy to go anywhere in this part of Florida, in fact the Disney parks are a dead straight run of around 15 to 25 minutes away (depending on traffic conditions) and Cocoa Beach is a nice straight drive along the express way if you want some sea and sand. It is always so nice if the owner is helpful and knowledgeable about the area and Helen is both of these, she is very hands on and always answers her phone messages. In conclusion I can say that if you are thinking of a Florida villa holiday DON'T HESITATE !!! to book this one.
                                                                                                      • Review Submitted: 05-Dec-2016
                                                                                                      • Date of Stay: Nov 2016