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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.

Additional service fee may apply.
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Excellent! 4.6/5
(8 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 3
House #709825vb
8
Viewed 52 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 6
Condo #724660vb
1
Viewed 23 times in the last 48 hours
Wonderful! 4.9/5
(11 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #243102
11
Viewed 46 times in the last 48 hours
Exceptional! 5/5
(14 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 5
House #466067vb
14
Viewed 67 times in the last 48 hours
Excellent! 4.7/5
(47 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 10
House #981770
47
Viewed 69 times in the last 48 hours
Excellent! 4.5/5
(10 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
House #450575vb
10
Viewed 30 times in the last 48 hours
Exceptional! 5/5
(17 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
Cottage #669117vb
17
Viewed 48 times in the last 48 hours
Exceptional! 5/5
(11 reviews)
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  • 4 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 8
House #3670851
11
Viewed 35 times in the last 48 hours
Exceptional! 5/5
(11 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Separate Toilet
  • Sleeps 2
Bungalow #444585vb
11
Viewed 23 times in the last 48 hours
Excellent! 4.4/5
(10 reviews)
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  • 2 BR
  • 1 BA
  • Sleeps 3
Bungalow #3993910
10
Viewed 98 times in the last 48 hours
Wonderful! 4.9/5
(14 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
House #3023348
14
Viewed 46 times in the last 48 hours
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Bungalow #780146vb
1
Viewed 47 times in the last 48 hours
Exceptional! 5/5
(6 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 6
House #823160vb
6
Viewed 86 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 112 times in the last 48 hours
Excellent! 4.7/5
(24 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 9
House #929474
24
Viewed 40 times in the last 48 hours
  • 4 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 8
House #885924vb
2
Viewed 33 times in the last 48 hours
Wonderful! 4.8/5
(5 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Apartment #683231vb
5
Viewed 8 times in the last 48 hours
Excellent! 4.7/5
(22 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 5
Bungalow #322808vb
22
Viewed 13 times in the last 48 hours
Exceptional! 5/5
(26 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Studio #493118vb
26
Viewed 16 times in the last 48 hours
Wonderful! 4.8/5
(27 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 9
House #929471
27
Viewed 31 times in the last 48 hours
Very Good! 4/5
(10 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 6
House #502419vb
10
Viewed 6 times in the last 48 hours
Wonderful! 4.8/5
(6 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 7
House #3166620
6
Viewed 15 times in the last 48 hours
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
House #990123vb
Viewed 19 times in the last 48 hours
  • 1 BR
  • 1 BA
  • Sleeps 2
Studio #4245895
3
Viewed 21 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 6
House #4303470
4
Viewed 45 times in the last 48 hours
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 5
Cottage #919138vb
1
Viewed 12 times in the last 48 hours
  • 4 BR
  • 2 BA
  • Sleeps 10
House #985828
Viewed 47 times in the last 48 hours
Excellent! 4.5/5
(2 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 8
House #901305vb
2
Viewed 10 times in the last 48 hours
Exceptional! 5/5
(13 reviews)
avg/night
  • 4 BR
  • 4 BA
  • Sleeps 8
Villa #305144vb
13
Viewed 50 times in the last 48 hours
Exceptional! 5/5
(10 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
House #3023034
10
Viewed 9 times in the last 48 hours
Exceptional! 5/5
(9 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
House #338205vb
9
Viewed 12 times in the last 48 hours
  • 3 BR
  • 3 BA
  • Sleeps 6
House #869308vb
  • 4 BR
  • 2 BA
  • Sleeps 10
House #694235vb
Viewed 11 times in the last 48 hours
Wonderful! 4.9/5
(10 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
House #319653vb
10
Viewed 11 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #809543vb
3
Viewed 130 times in the last 48 hours
Excellent! 4.7/5
(25 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 10
Condo #4141115
25
Viewed 283 times in the last 48 hours
Wonderful! 4.9/5
(86 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #964487
86
Viewed 91 times in the last 48 hours
Excellent! 4.6/5
(69 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Hotel #3905184
69
Viewed 390 times in the last 48 hours
Good! 3.9/5
(10 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #507153vb
10
Viewed 73 times in the last 48 hours
Exceptional! 5/5
(20 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
Villa #1869266
20
Viewed 48 times in the last 48 hours
Exceptional! 5/5
(6 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 8
House #4069886
6
Viewed 38 times in the last 48 hours
Excellent! 4.7/5
(15 reviews)
avg/night
  • 5 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 12
Villa #434457
15
Viewed 107 times in the last 48 hours
Exceptional! 5/5
(39 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
House #3569183
39
Viewed 30 times in the last 48 hours
Wonderful! 4.8/5
(29 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
House #4079570
29
Viewed 306 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 8
Multiple rentals Condo #407718
45
Viewed 114 times in the last 48 hours
Wonderful! 4.9/5
(11 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
House #656519vb
11
Viewed 80 times in the last 48 hours
Excellent! 4.7/5
(38 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 6
Townhome #297303vb
38
Viewed 35 times in the last 48 hours
Excellent! 4.7/5
(20 reviews)
avg/night
  • 1 BR
  • 2 BA
  • Sleeps 6
Condo #326140
20
Viewed 105 times in the last 48 hours
Wonderful! 4.9/5
(36 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #3727452
36
Viewed 67 times in the last 48 hours
Excellent! 4.5/5
(14 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 5
Condo #3834010
14
Viewed 106 times in the last 48 hours
  • 1 - 50 of 300+

Winter Park Holiday Rentals & Homes (300+)

 

Recent Reviews

Perfect Holiday and Business Escape

5 of 5
We used two of the 3 condos available at the beginning of February for a company convention. Our large group was accommodated perfectly and the owner was prompt in all responses. We highly recommend all of these properties because they are clean and centrally located to everything in Orlando.
  • Review Submitted: 21-Feb-2017
  • Date of Stay: Jan 2017