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

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

Things to do

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

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

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

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

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

Weather in Winter Park

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

Travel to Winter Park

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

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  • Showing 1-50 of 300+
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    Excellent! 4.7/5
    (6 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 3
    House #709825vb
    6
    Viewed 27 times in the last 48 hours
      Wonderful! 4.9/5
      (10 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 6
      House #243102
      10
      Viewed 11 times in the last 48 hours
        Exceptional! 5.0/5
        (10 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Separate Toilets
        • Sleeps 8
        House #3023034
        10
        Viewed 46 times in the last 48 hours
          Exceptional! 5.0/5
          (13 reviews)
          avg/night
          • 3 BR
          • 2 BA
          • Sleeps 5
          House #466067vb
          13
          Viewed 27 times in the last 48 hours
            Excellent! 4.7/5
            (44 reviews)
            avg/night
            • 3 BR
            • 3 BA
            • Sleeps 10
            House #981770
            44
            Viewed 67 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
                (16 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 4
                Cottage #669117vb
                16
                Viewed 32 times in the last 48 hours
                  Wonderful! 4.8/5
                  (21 reviews)
                  avg/night
                  • 3 BR
                  • 3 BA
                  • Sleeps 10
                  House #943873
                  21
                  Viewed 16 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 23 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 30 times in the last 48 hours
                        Exceptional! 5.0/5
                        (24 reviews)
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        Studio #493118vb
                        24
                        Viewed 21 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 13 times in the last 48 hours
                            • 4 BR
                            • 3 BA
                            • Separate Toilet
                            • Sleeps 8
                            House #885924vb
                            Viewed 22 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
                                • 3 BR
                                • 3 BA
                                • Sleeps 8
                                House #901305vb
                                Viewed 7 times in the last 48 hours
                                  Excellent! 4.7/5
                                  (15 reviews)
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Hotel #3905187
                                  15
                                  Viewed 217 times in the last 48 hours
                                    Excellent! 4.7/5
                                    (13 reviews)
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 10
                                    Condo #715037vb
                                    13
                                    Viewed 51 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (23 reviews)
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Separate Toilets
                                      • Sleeps 10
                                      House #786284vb
                                      23
                                      Viewed 87 times in the last 48 hours
                                        Excellent! 4.5/5
                                        (10 reviews)
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 8
                                        Villa #792155vb
                                        10
                                        Viewed 27 times in the last 48 hours
                                          Excellent! 4.7/5
                                          (13 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                          Villa #8012726
                                          13
                                          Viewed 19 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (13 reviews)
                                            avg/night
                                            • 5 BR
                                            • 4 BA
                                            • Separate Toilet
                                            • Sleeps 10
                                            Villa #790723vb
                                            13
                                            Viewed 56 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (12 reviews)
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 8
                                              Villa #647001vb
                                              12
                                              Viewed 23 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (25 reviews)
                                                avg/night
                                                • 5 BR
                                                • 4 BA
                                                • Separate Toilet
                                                • Sleeps 12
                                                Villa #1605033
                                                25
                                                Viewed 69 times in the last 48 hours
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 10
                                                  Condo #796272vb
                                                  4
                                                  Viewed 105 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (23 reviews)
                                                    avg/night
                                                    • 5 BR
                                                    • 4 BA
                                                    • Separate Toilet
                                                    • Sleeps 10
                                                    House #1670963
                                                    23
                                                    Viewed 32 times in the last 48 hours
                                                      Excellent! 4.6/5
                                                      (38 reviews)
                                                      avg/night
                                                      • 6 BR
                                                      • 4 BA
                                                      • Sleeps 14
                                                      Villa #318549vb
                                                      38
                                                      Viewed 21 times in the last 48 hours
                                                        Wonderful! 4.8/5
                                                        (25 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 2 BA
                                                        • Separate Toilet
                                                        • Sleeps 8
                                                        House #8063170
                                                        25
                                                        Viewed 36 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (19 reviews)
                                                          avg/night
                                                          • 4 BR
                                                          • 3 BA
                                                          • Sleeps 10
                                                          House #4084338
                                                          19
                                                          Viewed 12 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (10 reviews)
                                                            avg/night
                                                            • 5 BR
                                                            • 3 BA
                                                            • Separate Toilet
                                                            • Sleeps 10
                                                            Villa #8172417
                                                            10
                                                            Viewed 11 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (5 reviews)
                                                              avg/night
                                                              • 6 BR
                                                              • 5 BA
                                                              • Sleeps 12
                                                              Villa #887138vb
                                                              5
                                                              Viewed 73 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (28 reviews)
                                                                avg/night
                                                                • 5 BR
                                                                • 4 BA
                                                                • Separate Toilet
                                                                • Sleeps 12
                                                                Villa #1034900
                                                                28
                                                                Viewed 28 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (27 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 4 BA
                                                                  • Sleeps 10
                                                                  House #764845vb
                                                                  27
                                                                  Viewed 33 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (15 reviews)
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • Sleeps 10
                                                                    Villa #783837vb
                                                                    15
                                                                    Viewed 41 times in the last 48 hours
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      Villa #8017261
                                                                      3
                                                                      Viewed 22 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (24 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        Townhome #981760
                                                                        24
                                                                        Viewed 59 times in the last 48 hours
                                                                          Excellent! 4.6/5
                                                                          (12 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 10
                                                                          Villa #1623139
                                                                          12
                                                                          Viewed 5 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (12 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Separate Toilet
                                                                            • Sleeps 6
                                                                            House #8164116
                                                                            12
                                                                            Viewed 56 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (16 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Villa #1869266
                                                                              16
                                                                              Viewed 27 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (36 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                Villa #52814
                                                                                36
                                                                                Viewed 33 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (26 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Condo #614671vb
                                                                                  26
                                                                                  Viewed 23 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (18 reviews)
                                                                                    avg/night
                                                                                    • 9 BR
                                                                                    • 5 BA
                                                                                    • Sleeps 29
                                                                                    House #779965vb
                                                                                    18
                                                                                    Viewed 64 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (19 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      Cottage #813674vb
                                                                                      19
                                                                                      Viewed 25 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (44 reviews)
                                                                                        avg/night
                                                                                        • 5 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 10
                                                                                        Villa #1052432
                                                                                        44
                                                                                        Viewed 55 times in the last 48 hours
                                                                                          Excellent! 4.6/5
                                                                                          (19 reviews)
                                                                                          avg/night
                                                                                          • 5 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 10
                                                                                          House #689551vb
                                                                                          19
                                                                                          Viewed 45 times in the last 48 hours
                                                                                            Wonderful! 4.8/5
                                                                                            (12 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 8
                                                                                            Villa #1894882
                                                                                            12
                                                                                            Viewed 7 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (16 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Separate Toilets
                                                                                              • Sleeps 6
                                                                                              Townhome #3471004
                                                                                              16
                                                                                              Viewed 53 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (8 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 8
                                                                                                House #6479824
                                                                                                8
                                                                                                Viewed 36 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (19 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • Separate Toilet
                                                                                                  • Sleeps 10
                                                                                                  House #8035794
                                                                                                  19
                                                                                                  Viewed 26 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (38 reviews)
                                                                                                    avg/night
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 12
                                                                                                    Villa #287443
                                                                                                    38
                                                                                                    Viewed 28 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (18 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Separate Toilet
                                                                                                      • Sleeps 9
                                                                                                      House #8168973
                                                                                                      18
                                                                                                      Viewed 10 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Winter Park Holiday Homes & Villas (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Highly Recommend

                                                                                                      5 of 5
                                                                                                      I would highly recommend this town house, everything about it was of a high standard, clean and comfortable. The house is very well equipped with plenty of linens, towels, crockery etc. the terrace is a lovely area to dine out on and also relax after a full day out. The location of Compass Bay is ideally placed for access to all the parks, restaurants and shopping. Altogether a very enjoyable holiday, looking forward to going back to this town house again next year.
                                                                                                      • Review Submitted: 18-Nov-2016
                                                                                                      • Date of Stay: Oct 2016

                                                                                                      Lovely holiday villa

                                                                                                      5 of 5
                                                                                                      Lovely spacious villa in nice safe and quiet neighbourhood. Clean and well equipped. Good sized pool which is nice and private. Kids loved the games room. Close to restaurants, shops and the parks. Would highly recommend.
                                                                                                      • Review Submitted: 11-Nov-2016
                                                                                                      • Date of Stay: Jul 2016

                                                                                                      FANTASTIC!!

                                                                                                      5 of 5
                                                                                                      We were very pleased with the villa. It was spotlessly clean, spacious and very well equipped. All the parks were a mere 20-30 minute drive away. Before we arrived Owners Direct and the villa owner answered queries in a timely and friendly manner. Very friendly neighbours were happy to help with any queries / issues which gave us piece of mind. We would very much like to stay in this villa again. Highly recommended.
                                                                                                      • Review Submitted: 08-Nov-2016
                                                                                                      • Date of Stay: Oct 2016