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Winter Park, FL Cabins & Vacation Rentals

Price and Availability Index in Winter Park

Most expensive
Most availability
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The most expensive month to stay in a vacation rental in Winter Park is in July, while the cheapest month is in October. The most popular time to book a vacation rental in Winter Park is in the high season in December. Winter Park has its low season in September, when less people are visiting and the vacation home occupancy rate drops.

The cheapest day to stay at a vacation rental in Winter Park tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Winter Park tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The weather in Winter Park

85º 52º
0.42
86º 40º
0.4
86º 35º
2.08
86º 35º
2.08
90º 42º
0.16
96º 52º
0.06
96º 57º
3.38
94º 70º
10.43
96º 72º
5.96
96º 73º
2.79
95º 72º
11.31
91º 46º
3
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Rainy days
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This climate histogram shows you the weather patterns in Winter Park. The warmest months in Winter Park are June and September, when temperatures reach 96 ˚F. The coolest month is January, when temperatures drop to 35 ˚F. The wettest month in Winter Park is September with 11.31 inches of rain, while the driest month is April with 0.06 inches of rain.

Vacation Rentals in Winter Park

Choose the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, VRBO, Homeaway and more. AllTheRooms has 1400 vacation rentals, hotels and other great places to stay during your time in Winter Park, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. For those traveling on a budget, the cheapest place to stay in Winter Park is available at $10 per night. A typical accommodation in Winter Park costs on average $119 per night.

If you need an internet connection during your stay in Winter Park, then you can choose from over 265 places to stay that provide WiFi internet. We have 35 accommodations that come with a breakfast included. Choose from 33 places to stay that provide gym facilities, so you won't miss a single workout. If you're planning on arriving in Winter Park by car, be sure to choose from 255 accommodations that provide parking. 90 hotels and vacation rentals have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in one of 49 accommodations that are designated as pet-friendly.

We combine a wide variety of Winter Park accommodations including vacation rentals, homestays, hostels and other unique places to stay into one easy search. We show results from more than 6 providers, including 229 places to stay from Airbnb, 27 accommodations from VRBO and 14 places to stay from Homeaway.

1076 accommodations in Winter Park have been reviewed: 70% are rated excellent or good. You can instantly book any of 576 places to stay right now.

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