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Make a holiday apartment in Winter Park your home away from home

Located in a leafy suburb of Orlando, a Winter Park holiday apartment or villa is an ideal base for enjoying everything the metropolitan area has to offer, while providing a scenic and serene retreat from the hustle and bustle in the evenings. Planned and developed as a resort town at the turn of the 20th century, the brick-cobbled streets surrounding the rentals in Winter Park encourage strolling and browsing; perhaps stopping for a meal in one of the many upscale restaurants. With a wide range of villas, apartments, cabins and lodges to choose from, HomeAway offers Winter Park holiday accommodation to suit every taste.

Things to do

-Festivals: The annual Bach Festival is held every autumn at Winter Park's Rollins College Campus; a must if tourists have a passion for choral and classical music. March's Sidewalk Art Festival is one of the country's most prestigious, as is November's Winter Park Concours d'Elegance, for lovers of combustion-powered artistry of the four-wheeled variety.

-Gardens: Mead Botanical Garden encompasses 47 acres of parkland, and is typically within walking distance of most Winter Park holiday rentals. It boasts a number of ecosystems to explore by foot on the boardwalk, or by bicycle on the bike trails. A 300 seater amphitheatre also anchors this urban oasis, along with a discovery barn, butterfly garden and a recreation centre.

-History: Many of the buildings surrounding rentals in Winter Park are over 100 years old, which is a real rarity in the US with their propensity for constant urban renewal. They shoulder tree-shaded and brick-cobbled streets, and abut the Venetian canals, blending elegantly with picturesque lakes and meticulous parks.

-Theme Parks: While Winter Park holiday rentals are sited in a peaceful, quaint town, Orlando has some of the most exciting theme parks in the world. From behemoths like Disney World, Universal Studios and Sea World, to smaller parks like Legoland, the Kennedy Space Centre Visitor Complex, the Holy Land Experience and Gatorland, tourists can easily do a theme park a day!

-Nightlife: Eating out is typically quite high end in Winter Park, matching the atmosphere of this quaint and elegant town. From French bistros to tapas bars, BBQ joints to fusion fare, there's a venue for every taste and budget, but the tendency is towards fine dining. Bars and nightclubs are equally cosmopolitan.

Weather in Winter Park

Winter Park has a typical Florida subtropical climate, with warm, dry winters and long, hot summers, encouraging the eponymous notion of the town as a winter destination. Rain falls mainly during the summer as heavy thunderstorms, breaking the humidity and also helping to keep things cooler than inland areas further north. Temperatures from June to September top out at around the mid-30°C mark, while winter maximums hover around 22°C: it’s about the same as a British summer.

Travel to Winter Park

Travel to Winter Park is a cinch as Orlando International Airport is only 14 miles away. Unusually for Florida, visitors could feasibly get around on Orlando's public transport. This is often undesirable, however, especially during the summer with the heat, humidity, and frequent cloudbursts. Fly/drive is still preferable, despite Orlando's extensive public transport system. There is an Amtrak station in Winter Park itself, if guests fancy an iconic American train journey, though Amtrak is a national network rather than a local one.

    Excellent! 4.6/5
    (12 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 4
    House #450575vb
    12
    Viewed 25 times in the last 48 hours
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 4
      Bungalow #780146vb
      4
      Viewed 14 times in the last 48 hours
        Exceptional! 5/5
        (15 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Separate Toilet
        • Sleeps 2
        Bungalow #444585vb
        15
        Viewed 22 times in the last 48 hours
          Wonderful! 4.8/5
          (52 reviews)
          avg/night
          • 3 BR
          • 3 BA
          • Sleeps 10
          House #981770
          52
          Viewed 29 times in the last 48 hours
            Excellent! 4.4/5
            (16 reviews)
            avg/night
            • 2 BR
            • 1 BA
            • Sleeps 3
            Bungalow #3993910
            16
            Viewed 26 times in the last 48 hours
              • 4 BR
              • 3 BA
              • Separate Toilet
              • Sleeps 8
              House #885924vb
              4
              Viewed 14 times in the last 48 hours
                avg/night
                • 2 BR
                • 1 BA
                • Sleeps 5
                Cottage #919138vb
                2
                Viewed 14 times in the last 48 hours
                  Excellent! 4.7/5
                  (24 reviews)
                  avg/night
                  • 2 BR
                  • 2 BA
                  • Sleeps 5
                  Bungalow #322808vb
                  24
                  Viewed 6 times in the last 48 hours
                    Wonderful! 4.9/5
                    (7 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                    Apartment #683231vb
                    7
                    Viewed 6 times in the last 48 hours
                      Exceptional! 5/5
                      (10 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Separate Toilet
                      • Sleeps 6
                      House #823160vb
                      10
                      Viewed 34 times in the last 48 hours
                        Excellent! 4.6/5
                        (31 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 9
                        House #929474
                        31
                        Viewed 31 times in the last 48 hours
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          House #1069947vb
                          Viewed 7 times in the last 48 hours
                            Wonderful! 4.8/5
                            (21 reviews)
                            avg/night
                            • 4 BR
                            • 2 BA
                            • Sleeps 10
                            House #3023348
                            21
                            Viewed 23 times in the last 48 hours
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              House #1027239vb
                              Viewed 7 times in the last 48 hours
                                Exceptional! 5/5
                                (20 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 4
                                Cottage #669117vb
                                20
                                Viewed 11 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (30 reviews)
                                  avg/night
                                  • 3 BR
                                  • 3 BA
                                  • Separate Toilet
                                  • Sleeps 9
                                  House #929471
                                  30
                                  Viewed 15 times in the last 48 hours
                                    Exceptional! 5/5
                                    (28 reviews)
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    Studio #493118vb
                                    28
                                    Viewed 6 times in the last 48 hours
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 8
                                      House #990123vb
                                      2
                                      Viewed 10 times in the last 48 hours
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 5
                                        House #952054vb
                                        3
                                        Viewed 28 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (11 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          House #243102
                                          11
                                          Viewed 16 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (6 reviews)
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 2
                                            Studio #4245895
                                            6
                                            Viewed 23 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (4 reviews)
                                              avg/night
                                              • 3 BR
                                              • 3 BA
                                              • Sleeps 8
                                              House #901305vb
                                              4
                                              Viewed 9 times in the last 48 hours
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Separate Toilet
                                                • Sleeps 6
                                                House #4303470
                                                6
                                                Viewed 33 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (6 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 1 BA
                                                  • Sleeps 7
                                                  House #3166620
                                                  6
                                                  Viewed 16 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (12 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    House #3023034
                                                    12
                                                    Viewed 14 times in the last 48 hours
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 7
                                                      House #1030436vb
                                                      1
                                                      Viewed 11 times in the last 48 hours
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                        Apartment #1069352vb
                                                        Viewed 28 times in the last 48 hours
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          Apartment #1046545vb
                                                          Viewed 44 times in the last 48 hours
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Guest House #1033184vb
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Condo #724660vb
                                                              2
                                                              Viewed 7 times in the last 48 hours
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 2
                                                                House #1091039vb
                                                                Viewed 6 times in the last 48 hours
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 4
                                                                  House #1060352vb
                                                                  Viewed 12 times in the last 48 hours
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    House #1097929vb
                                                                    Viewed 18 times in the last 48 hours
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      House #1056448vb
                                                                      Viewed 6 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
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          House #338205vb
                                                                          9
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Sleeps 10
                                                                            House #694235vb
                                                                            Viewed 18 times in the last 48 hours
                                                                              Excellent! 4.7/5
                                                                              (127 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Hotel #3905183
                                                                              127
                                                                              Viewed 559 times in the last 48 hours
                                                                                Excellent! 4.6/5
                                                                                (37 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 10
                                                                                Condo #4141115
                                                                                37
                                                                                Viewed 296 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (9 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  House #792993vb
                                                                                  9
                                                                                  Viewed 62 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (66 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 10
                                                                                    Villa #34854vb
                                                                                    66
                                                                                    Viewed 313 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (89 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                      Condo #964487
                                                                                      89
                                                                                      Viewed 117 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (45 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        House #3569183
                                                                                        45
                                                                                        Viewed 7 times in the last 48 hours
                                                                                          Very Good! 4/5
                                                                                          (15 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          House #507153vb
                                                                                          15
                                                                                          Viewed 40 times in the last 48 hours
                                                                                            Excellent! 4.6/5
                                                                                            (53 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 9
                                                                                            Villa #56513
                                                                                            53
                                                                                            Viewed 50 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (34 reviews)
                                                                                              avg/night
                                                                                              • 5 BR
                                                                                              • 5 BA
                                                                                              • Separate Toilet
                                                                                              • Sleeps 10
                                                                                              Villa #331193
                                                                                              34
                                                                                              Viewed 173 times in the last 48 hours
                                                                                                Very Good! 4.1/5
                                                                                                (34 reviews)
                                                                                                avg/night
                                                                                                • Studio
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                Studio #911234vb
                                                                                                34
                                                                                                Viewed 143 times in the last 48 hours
                                                                                                  Excellent! 4.6/5
                                                                                                  (94 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Hotel #3905184
                                                                                                  94
                                                                                                  Viewed 233 times in the last 48 hours
                                                                                                    Excellent! 4.5/5
                                                                                                    (48 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 8
                                                                                                    Villa #164801
                                                                                                    48
                                                                                                    Viewed 141 times in the last 48 hours
                                                                                                      Exceptional! 5/5
                                                                                                      (25 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Villa #1869266
                                                                                                      25
                                                                                                      Viewed 36 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Winter Park Holiday Rentals & Homes (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Perfect for your Orlando experience!

                                                                                                      5 of 5
                                                                                                      Firstly, can't speak highly enough of the owners Chris and Chris. They really take care of you and want to make sure you have all the information you need and are more than happy to answer questions, no matter how silly they may be. The villa is situated in a quiet residential area. When we were there, next door was also British tourists. The neighbours are obviously use to tourist and are helpful. Locals even knocked the door to tell us we left the light on our hire car! The villa pools temperature was perfect with solar power during our may to June stay. There is a net cover over the whole pool which minimises any bugs! You do see many lizards though! Outside the net ofcourse. The villa is like home from home. It has all of the things you will need. Even down to ironing and hair dryers. I would recommend a trip to the super market before you arrive. We were a late arrival (8pm) and had to go out almost straight away as the villa doesn't have any consumables. Milk sugar and tea bags would have been a nice touch. The villa was lovely and clean. The garage is large and will fit most cars. We didn't use it though because the drive was good enough. The location of the villa is good. It is about 25 minutes to get to universal and international drive. But there is also walmat and many restaurants less than 5 minutes away. Gatorland it's very close, but Kennedy Space Centre is about an hour away, but it is well worth the drive! We had access to the villa with no issues. You just need to follow the instruction on the app to get the key. It very much is home from home. We didn't hear from anyone from the management company until the day before we left, so it is quite hands off. Suited us fine, but others may like a welcome call or something l, just for reassurance. All in all it was a good choice for us and met our needs perfectly. Would definitely stay again no question about it. Thank you C and C. (Cook-Youngs Wales).
                                                                                                      • Review Submitted: Jun 09, 2017
                                                                                                      • Date of Stay: May 2017

                                                                                                      So glad to have chosen to stay here

                                                                                                      5 of 5
                                                                                                      I stayed here for two weeks in April 2011 having travelled from England with my daughter and my parents. I really do have nothing but good things to say about it and would recommend it to anybody looking for a quality property near to Disneyland. The villa is very well proportioned and well maintained, and has all the comforts of home including appliances, wireless internet and three TVs (one with DVD player) and even an iPod dock. The kitchen has good storage and plentiful crockery, utensils etc. The master bedroom is impressive as is the en suite and dressing room, and the other three bedrooms and two bathrooms are more than adequate for adults or children to use. The pool was clean and warm (even though we chose not to heat it). I loved the little details like board games, DVDs and books for the children, plentiful towels, instructions for all the appliances and the folder of local information. The development which the villa is on is quiet, but not so quiet that you can't enjoy yourself. The clubhouse was a great amenity that provides services such as ticket and newspaper sales and dvd rentals as well as the pool, gym etc. They also put on events such as an Easter Egg Hunt which my daughter loved, and a cook out. The owner of the property was extremely efficient, answered all queries etc very quickly and thoroughly and also provided local information that proved very useful to us. There is also a local management contact that you can call if you have any issues - I called them when I was unable to operate the washing machine (due to my own stupidity!) and they came round quickly to help. The villa is about 20 minutes drive to Disney, 45 minutes from the airport and is close to local shops and restaurants. This was the first time I have used the internet to choose a privately owned property and I was nervous about it. However, when I arrived I was relieved to discover that the nerves had been unneccesary, and I had chosen very well. If you are looking for a property to rent, you would do well to choose this one.
                                                                                                      • Review Submitted: May 01, 2011
                                                                                                      • Date of Stay: Apr 2011