HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr

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.

Cancel Clear Filters Apply Filters

Property Type

Popular Searches

Payment Options

Facilities

Managed By

Local Area

Property Details

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Winter Park Holiday Rentals & Homes (1,248)

  • 1 - 50 of 1,248
    • 3 BR
    • 2 BA
    • Sleeps 6
    9
      • 3 BR
      • 2 BA
      • Separate Toilets
      • Sleeps 8
      9
        • 3 BR
        • 2 BA
        • Sleeps 5
        12
          • 2 BR
          • 1 BA
          • Sleeps 3
          6
            • 3 BR
            • 2 BA
            • Separate Toilet
            • Sleeps 8
            10
              • 2 BR
              • 2 BA
              • Sleeps 4
              14
                • 1 BR
                • 1 BA
                • Sleeps 2
                24
                  NEW!
                  • 4 BR
                  • 3 BA
                  • Separate Toilet
                  • Sleeps 8
                    • 4 BR
                    • 2 BA
                    • Separate Toilet
                    • Sleeps 8
                    9
                      • 1 BR
                      • 1 BA
                      • Separate Toilet
                      • Sleeps 2
                      10
                        • 3 BR
                        • 3 BA
                        • Sleeps 10
                        20
                          • 3 BR
                          • 2 BA
                          • Separate Toilet
                          • Sleeps 6
                          5
                            • 3 BR
                            • 3 BA
                            • Sleeps 10
                            41
                              • 3 BR
                              • 2 BA
                              • Sleeps 9
                              20
                                • 2 BR
                                • 2 BA
                                • Sleeps 5
                                20
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 2
                                  3
                                    NEW!
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    2 Reviews
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 3
                                      7
                                        • 3 BR
                                        • 3 BA
                                        • Sleeps 6
                                        10
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          9
                                            • 3 BR
                                            • 3 BA
                                            • Separate Toilet
                                            • Sleeps 8
                                            24
                                              NEW!
                                              • 3 BR
                                              • 3 BA
                                              • Sleeps 8
                                                NEW!
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                  NEW!
                                                  • 3 BR
                                                  • 3 BA
                                                  • Sleeps 6
                                                    • 3 BR
                                                    • 1 BA
                                                    • Sleeps 7
                                                    6
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      9
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 10
                                                        7
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                              NEW!
                                                              • 5 BR
                                                              • 3 BA
                                                              • Sleeps 12
                                                              2 Reviews
                                                                • 4 BR
                                                                • 4 BA
                                                                • Sleeps 8
                                                                12
                                                                  • 5 BR
                                                                  • 5 BA
                                                                  • Sleeps 10
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 10
                                                                      • 6 BR
                                                                      • 5 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 15
                                                                      8
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 7
                                                                        1 Review
                                                                          NEW!
                                                                          • 2 BR
                                                                          • 3 BA
                                                                          • Sleeps 5
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 2
                                                                            4
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              2 Reviews
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                37
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 8
                                                                                    2 Reviews
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 5
                                                                                      15
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 5
                                                                                        3
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          8
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 10
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 10
                                                                                                16
                                                                                                  NEW!
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 2
                                                                                                  3
                                                                                                    • 3 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 10
                                                                                                    12
                                                                                                    • 1 - 50 of 1,248