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Winter Park, FL Cabins & Vacation Rentals

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Winter Park Travel Guide

Contrary to its name, Winter Park is a ray of sunshine with lots to offer tourists with different interests. This historic and quaint town is family-friendly, with opportunity to enjoy arts, culture and nature all in one. There are famous museums and festivals held throughout the year, with over 70 green spaces for nature-lovers to explore. You'll also find a lot of cafes and coffee spots for the health-conscious travelers, as well as weekly farmer’s markets. It isn’t hard to see how Winter Park has become a favourite retreat in the Sunshine State for many families and couples on vacation.

Things to Do in Winter Park

You'll find one of the oldest attractions in Florida in Winter Park -- Scenic Boat Tours. A guide takes you out onto Lake Osceola to admire the flora and see if you can spot any 'gators. Winter Park Sidewalk Art Festival attracts visitors annually since it is one of the oldest and largest outdoor art festivals in the country. You can wander around Olde Winter Park and explore the traditional, brick streets and unwind in the Mead Botanical Garden, with over 48 acres of greenery. The Charles Hosmer Morse Museum of American Art also showcases the best works of artist, Louis Comfort Tiffany in the world.

Best Time to Visit Winter Park

The best time to visit Winter Park is from January to April when it's still warm but there is less rain and humidity to make it comfortable. While a lot of tourists visit this city in the Sunshine State during the summer months, Winter Park is at its hottest and most humid from May to the end of August. This is hurricane season and means the potential for storms that could affect your plans.

Cabins in Winter Park

The town of Winter Park is the perfect base village for a skiing adventure. The continental divide cuts right through Grand County, giving a stunning backdrop to all slopes in Winter Park Colorado. Winter Park Resort features 3,000 acres of award-winning terrain, with runs suitable for all abilities, as well as a large number of vacation rentals.

The fun doesn't stop in summer, and the Winter Park area becomes crowded with mountain bike enthusiasts, meaning rentals in Winter Park and nearby Fraser Valley tend to fill up during this season. The valley is surrounded by the Arapaho National Forest which is criss-crossed with a number of hiking trails -- the idea setting for any outdoor enthusiast!

Winter Park lodging fits a range of budgets. For something a little more luxurious, book a rental with a hot tub where you can soak up the surrounding mountain views. The majority of Winter Park cabin rentals have full kitchens, and many are ski-in ski-out condos, meaning you have immediate access to world-class skiing. Trailhead Lodge offers a number of 1-3 bedroom accomodations close to all of the action, or there are a number of other management companies visitors can book through.

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Price and Availability in Winter Park

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The cheapest day to stay at a vacation rental in Winter Park tends to be Monday, 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 Mondays.
The most expensive month to stay in a vacation rental in Winter Park is in July, while the cheapest month is in April. The most popular time to book a vacation rental in Winter Park is in the high season in March. Winter Park has its low season in September, when less people are visiting and the vacation home occupancy rate drops.
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The Weather in Winter Park

Rainy days
98° 72°
6
97° 73°
13
95° 69°
3
92° 68°
6
89° 49°
1
85° 42°
4
83° 38°
3
88° 48°
2
88° 42°
2
91° 56°
2
98° 66°
4
98° 71°
12
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Rainy days

This climate histogram shows you the weather patterns in Winter Park. The hottest month in Winter Park is July, when temperatures peak at 98 ˚F. The coolest month is December, when temperatures drop to 38 ˚F. The wettest month in Winter Park is May with 13.03 inches of rain, while the driest month is February with 1.33 inches of rain.

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Vacation Rentals in Winter Park

Browse places to stay from all your favorite providers including Airbnb, Priceline, RedAwning and many more at AllTheRooms.com. Winter Park has 496 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, extravagant travelers and everything in between. For those wanting to keep costs down, the cheapest place to stay in Winter Park comes in at $10 a night. A typical rental in Winter Park costs on average $110 a night.

If you have to have an internet connection during your time in Winter Park, then you can choose from over 357 places to stay that have WiFi internet. 41 places to stay include a morning meal. You can keep up with your workout regime by staying at one of 51 accommodations that provide gym facilities. Driving to Winter Park? Then choose one of the 347 places to stay that comes with a parking spot included. 135 hotels and vacation rentals come with a pool or jacuzzi

If you're traveling with a furry friend, then make sure to choose one of the 70 pet-friendly accommodations available.

376 of our rentals in Winter Park have been reviewed by previous guests. They rated 70% as great. 205 accommodations allow instant booking.

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