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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.

  • Showing 1-50 of 300+
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    Excellent! 4.6/5
    (8 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 3
    House #709825vb
    8
    Viewed 42 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 18 times in the last 48 hours
        Wonderful! 4.9/5
        (11 reviews)
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        • 3 BR
        • 2 BA
        • Sleeps 6
        House #243102
        11
        Viewed 48 times in the last 48 hours
          Exceptional! 5.0/5
          (13 reviews)
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          • 3 BR
          • 2 BA
          • Sleeps 5
          House #466067vb
          13
          Viewed 44 times in the last 48 hours
            Excellent! 4.7/5
            (47 reviews)
            avg/night
            • 3 BR
            • 3 BA
            • Sleeps 10
            House #981770
            47
            Viewed 101 times in the last 48 hours
              • 3 BR
              • 2 BA
              • Sleeps 6
              Condo #724660vb
              1
              Viewed 7 times in the last 48 hours
                Wonderful! 4.8/5
                (23 reviews)
                avg/night
                • 3 BR
                • 3 BA
                • Sleeps 10
                House #943873
                23
                Viewed 56 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 24 times in the last 48 hours
                    Exceptional! 5.0/5
                    (17 reviews)
                    avg/night
                    • 2 BR
                    • 2 BA
                    • Sleeps 4
                    Cottage #669117vb
                    17
                    Viewed 25 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 98 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 22 times in the last 48 hours
                          Wonderful! 4.8/5
                          (13 reviews)
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                          • 4 BR
                          • 2 BA
                          • Sleeps 10
                          House #3023348
                          13
                          Viewed 31 times in the last 48 hours
                            Exceptional! 5.0/5
                            (24 reviews)
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                            • 1 BR
                            • 1 BA
                            • Sleeps 2
                            Studio #493118vb
                            24
                            Viewed 25 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 43 times in the last 48 hours
                                Excellent! 4.7/5
                                (24 reviews)
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 9
                                House #929474
                                24
                                Viewed 41 times in the last 48 hours
                                  Excellent! 4.3/5
                                  (9 reviews)
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                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 3
                                  Bungalow #3993910
                                  9
                                  Viewed 32 times in the last 48 hours
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    Apartment #683231vb
                                    4
                                    Viewed 22 times in the last 48 hours
                                      Very Good! 4.0/5
                                      (10 reviews)
                                      avg/night
                                      • 3 BR
                                      • 3 BA
                                      • Sleeps 6
                                      House #502419vb
                                      10
                                      Viewed 5 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
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                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Bungalow #780146vb
                                          1
                                          Viewed 9 times in the last 48 hours
                                            • 4 BR
                                            • 3 BA
                                            • Separate Toilet
                                            • Sleeps 8
                                            House #885924vb
                                            2
                                            Viewed 33 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (26 reviews)
                                              avg/night
                                              • 3 BR
                                              • 3 BA
                                              • Separate Toilet
                                              • Sleeps 9
                                              House #929471
                                              26
                                              Viewed 36 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (6 reviews)
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                                                • 3 BR
                                                • 1 BA
                                                • Sleeps 7
                                                House #3166620
                                                6
                                                Viewed 7 times in the last 48 hours
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                  Studio #4245895
                                                  3
                                                  Viewed 28 times in the last 48 hours
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 10
                                                    House #694235vb
                                                    Viewed 17 times in the last 48 hours
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                                                      • 3 BR
                                                      • 2 BA
                                                      • Separate Toilet
                                                      • Sleeps 6
                                                      House #4303470
                                                      3
                                                      Viewed 44 times in the last 48 hours
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                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 5
                                                        Cottage #919138vb
                                                        1
                                                        Viewed 30 times in the last 48 hours
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 8
                                                          House #901305vb
                                                          2
                                                          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 50 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (9 reviews)
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                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              House #338205vb
                                                              9
                                                              Viewed 11 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (10 reviews)
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                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                House #3023034
                                                                10
                                                                Viewed 20 times in the last 48 hours
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                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 5
                                                                  House #952054vb
                                                                  Viewed 32 times in the last 48 hours
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                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    House #990123vb
                                                                    Viewed 18 times in the last 48 hours
                                                                      • 3 BR
                                                                      • 3 BA
                                                                      • Sleeps 6
                                                                      House #869308vb
                                                                        Wonderful! 4.9/5
                                                                        (10 reviews)
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                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        House #319653vb
                                                                        10
                                                                        Viewed 13 times in the last 48 hours
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Condo #809544vb
                                                                          1
                                                                          Viewed 31 times in the last 48 hours
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            Condo #809543vb
                                                                            2
                                                                            Viewed 156 times in the last 48 hours
                                                                              Excellent! 4.7/5
                                                                              (22 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 10
                                                                              Condo #4141115
                                                                              22
                                                                              Viewed 252 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (82 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                Condo #964487
                                                                                82
                                                                                Viewed 114 times in the last 48 hours
                                                                                  Good! 3.9/5
                                                                                  (10 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  House #507153vb
                                                                                  10
                                                                                  Viewed 78 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (28 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 10
                                                                                    House #4079570
                                                                                    28
                                                                                    Viewed 381 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 107 times in the last 48 hours
                                                                                        Wonderful! 4.8/5
                                                                                        (8 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 3
                                                                                        Cottage #490078vb
                                                                                        8
                                                                                        Viewed 83 times in the last 48 hours
                                                                                          Excellent! 4.7/5
                                                                                          (20 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          Condo #326140
                                                                                          20
                                                                                          Viewed 97 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (63 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Hotel #3905183
                                                                                            63
                                                                                            Viewed 489 times in the last 48 hours
                                                                                              Excellent! 4.7/5
                                                                                              (58 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Hotel #3905184
                                                                                              58
                                                                                              Viewed 427 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (18 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                Villa #1869266
                                                                                                18
                                                                                                Viewed 42 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (39 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  House #3569183
                                                                                                  39
                                                                                                  Viewed 20 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (11 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    House #656519vb
                                                                                                    11
                                                                                                    Viewed 53 times in the last 48 hours
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 6
                                                                                                      Condo #7032028
                                                                                                      3
                                                                                                      Viewed 48 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Winter Park Holiday Rentals & Homes (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Florida December 2016

                                                                                                      5 of 5
                                                                                                      Before arriving Chris e-mailed us directions from the Orlando airport ( which he recommended a car rental which was very easy). Fabulous directions no problems and even told us a grocery store to stop at so we could just arrive at their house and relax. The house is very clean and had everything we needed including some spices and all dishes and appliances you will ever need. We paid extra for heat in the pool which at first we thought was way to warm at 92 but after a day at the theme parks it was fabulous to have a drink and relax by the pool. Also anytime we e-mailed before we left with questions Chris got back to us within minutes. Great place and I would highly recommend their place and looking forward to going again. Neil and Susan.
                                                                                                      • Review Submitted: 03-Jan-2017
                                                                                                      • Date of Stay: Dec 2016

                                                                                                      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