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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
(13 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
House #450575vb
13
Viewed 21 times in the last 48 hours
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  • 2 BR
  • 1 BA
  • Sleeps 4
Bungalow #780146vb
4
Viewed 8 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 10 times in the last 48 hours
Wonderful! 4.8/5
(53 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 10
House #981770
53
Viewed 42 times in the last 48 hours
Excellent! 4.5/5
(19 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 3
Bungalow #3993910
19
Viewed 26 times in the last 48 hours
Excellent! 4.7/5
(24 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 5
Bungalow #322808vb
24
Viewed 5 times in the last 48 hours
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 5
Cottage #919138vb
2
Viewed 9 times in the last 48 hours
Exceptional! 5/5
(6 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 8
House #885924vb
6
Viewed 16 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 25 times in the last 48 hours
Excellent! 4.6/5
(31 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 9
House #929474
31
Viewed 139 times in the last 48 hours
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  • 1 BR
  • 1 BA
  • Sleeps 2
House #1069947vb
Viewed 25 times in the last 48 hours
  • 2 BR
  • 2 BA
  • Sleeps 4
House #1027239vb
Wonderful! 4.8/5
(30 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 9
House #929471
30
Viewed 42 times in the last 48 hours
Wonderful! 4.8/5
(21 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
House #3023348
21
Viewed 36 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
  • 2 BR
  • 2 BA
  • Sleeps 4
Cottage #669117vb
20
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
House #990123vb
3
Viewed 8 times in the last 48 hours
Wonderful! 4.8/5
(4 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 8
House #901305vb
4
Viewed 12 times in the last 48 hours
Wonderful! 4.9/5
(11 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #243102
11
Viewed 6 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 6
House #4303470
6
Viewed 29 times in the last 48 hours
Wonderful! 4.8/5
(6 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 7
House #3166620
6
Viewed 7 times in the last 48 hours
Exceptional! 5/5
(12 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
House #3023034
12
Viewed 10 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 7
House #1030436vb
1
Viewed 12 times in the last 48 hours
Excellent! 4.7/5
(7 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Studio #4245895
7
Viewed 23 times in the last 48 hours
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  • 2 BR
  • 2 BA
  • Sleeps 4
Apartment #1069352vb
Viewed 10 times in the last 48 hours
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  • 2 BR
  • 1 BA
  • Sleeps 4
House #1097929vb
Viewed 12 times in the last 48 hours
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  • 1 BR
  • 1 BA
  • Sleeps 6
Apartment #1046545vb
Viewed 7 times in the last 48 hours
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  • 1 BR
  • 1 BA
  • Sleeps 2
Guest House #1033184vb
Viewed 5 times in the last 48 hours
  • 4 BR
  • 2 BA
  • Sleeps 10
House #694235vb
Viewed 21 times in the last 48 hours
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  • 1 BR
  • 1 BA
  • Sleeps 2
House #1114835vb
Viewed 5 times in the last 48 hours
  • 2 BR
  • 2 BA
  • Sleeps 6
House #1129469vb
  • 1 BR
  • 1 BA
  • Sleeps 2
House #4628707
  • 2 BR
  • 2 BA
  • Sleeps 4
House #1060352vb
Viewed 14 times in the last 48 hours
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  • 1 BR
  • 1 BA
  • Sleeps 2
House #1091039vb
Viewed 9 times in the last 48 hours
  • 1 BR
  • 1 BA
  • Sleeps 2
House #1114504vb
Viewed 16 times in the last 48 hours
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  • 2 BR
  • 1 BA
  • Sleeps 4
Condo #1127343vb
Viewed 9 times in the last 48 hours
  • 1 BR
  • 1 BA
  • Sleeps 2
House #1114391vb
Viewed 9 times in the last 48 hours
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  • 2 BR
  • 1 BA
  • Sleeps 6
Condo #4626354
Viewed 18 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 6
Condo #724660vb
2
avg/night
  • 1 BR
  • 1 BA
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House #1114809vb
Viewed 9 times in the last 48 hours
  • 2 BR
  • 1 BA
  • Sleeps 4
House #1056448vb
Viewed 38 times in the last 48 hours
  • 4 BR
  • 2 BA
  • Sleeps 8
House #319653vb
10
Exceptional! 5/5
(9 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
House #338205vb
9
Viewed 7 times in the last 48 hours
  • 1 BR
  • 1 BA
  • Sleeps 2
House #1136926vb
Viewed 9 times in the last 48 hours
Excellent! 4.7/5
(134 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Hotel #3905183
134
Viewed 510 times in the last 48 hours
Wonderful! 4.8/5
(9 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #792993vb
9
Viewed 90 times in the last 48 hours
Excellent! 4.6/5
(41 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 10
Condo #4141115
41
Viewed 383 times in the last 48 hours
Wonderful! 4.8/5
(45 reviews)
avg/night
  • 1 BR
  • 2 BA
  • Sleeps 6
Condo #512028vb
45
Viewed 203 times in the last 48 hours
Excellent! 4.6/5
(28 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #746426vb
28
Viewed 150 times in the last 48 hours

Winter Park Holiday Rentals & Homes (300+)