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Winter Park, FL Cabins & Vacation Rentals

Our Favorite Vacation Rentals in Winter Park

Winter Park Vacation Rentals with a Pool

Winter Park Vacation Rentals with Wi-Fi

Winter Park Pet-Friendly Vacation Rentals

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.

Price and Availability in Winter Park

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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 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.
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 Weather in Winter Park

95º 72º
95º 73º
96º 74º
93º 56º
87º 39º
86º 40º
84º 28º
88º 49º
88º 43º
90º 53º
94º 64º
95º 71º
Rainy days
This climate histogram shows you the weather patterns in Winter Park. The warmest months in Winter Park are April and June, when temperatures reach 96 ˚F. The coolest month is January, when temperatures drop to 28 ˚F. The wettest month in Winter Park is August with 10.3 inches of rain, while the driest month is February with 0.33 inches of rain.

What Expert Travelers Think

Vacation Rentals in Winter Park

Browse rentals from all the leading providers including Airbnb, Priceline, RedAwning and more at We have 401 vacation rentals, hotels and other accommodation types in Winter Park ranging from inexpensive options to luxury places to stay. A trip to Winter Park can be budget-friendly - our cheapest price rental is available at $10 a night. The average price of a rental is around $113 per night.

If you want internet access during your stay in Winter Park, then you can choose from over 302 places to stay that provide WiFi internet. 36 of our accommodations include a breakfast in the price. You can maintain your workout routine by staying at one of 36 accommodations that provide gym facilities. If you are driving to Winter Park, you'll want to pick from 294 places to stay that provide parking. We have 102 hotels and vacation rentals that have a pool or jacuzzi.

If you're traveling with your best friend, then make sure to select one of the 64 pet-friendly accommodations available.

308 of our accommodations in Winter Park have been reviewed and rated. 70% are rated excellent or good. You can instantly book any of 174 places to stay right now.

Destinations near Winter Park