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Winter Park, FL Cabins & 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.

Price and Availability Index 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 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

86º 35º
85º 46º
90º 42º
96º 52º
96º 57º
94º 70º
96º 72º
96º 73º
95º 72º
91º 46º
85º 52º
86º 40º
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. Winter Park has 1480 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those traveling on a budget, the cheapest place to stay in Winter Park is available at $10 per night. The average price of accommodation in is $125 per night.

If you need an internet connection during your stay in Winter Park, then you can choose from over 544 places to stay that provide WiFi internet. 58 of our accommodations in include a breakfast in the price. Fitness addicts can get a workout in during their stay by choosing from 60 accommodations that have gym facilities. If you're planning on arriving in Winter Park by car, be sure to choose from 526 accommodations that provide parking. 190 hotels and vacation rentals have a pool or jacuzzi.

AllTheRooms has 102 pet-friendly places to stay in Winter Park, so if you're travelling with your cat or dog you won't have any trouble.

AllTheRooms aggregates vacation rentals, hotels and other unique accommodation types from 6 providers in Winter Park, including 476 places to stay from Airbnb, 54 accommodations from VRBO and 26 places to stay from Homeaway

1132 accommodations in Winter Park have been reviewed: 71% are rated excellent or good. 632 places to stay in are instantly bookable.

Destinations near Winter Park

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