Vacation rentals in Winter Park, FL
Search and compare Winter Park, FL vacation rentals from hundreds of travel sites on HotelsCombined and save.
Winter Park, United States
Apr 8 — Apr 92
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Travel insights for vacation rentals in Winter Park
Use our HotelsCombined data-powered tips to help you find your next vacation rental in Winter Park.
What is the cheapest month to book a vacation rental in Winter Park?
The cheapest month to book a vacation rental in Winter Park is November ($108). Conversely, the most expensive month to stay in Winter Park is February ($534).
What is the cheapest day to stay in a vacation rental in Winter Park?
The cheapest day to stay in Winter Park is Tuesday ($152). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $453.
Other accommodations in Winter Park, FL
Find the perfect vacation rental for your stay in Winter Park, FL. There are 76 hotels in Winter Park, FL and price data was last updated on April 1, 2025. The average price for a hotel in Winter Park, FL is $234/night.
Show all 76 stays
300 East New England Avenue, Winter Park, FL, United States
0.6 mi from city centre
Free Wi-Fi
$282
Avg. per night
307 South Park Avenue , Winter Park, FL, United States
0.8 mi from city centre
Free Wi-Fi
$179
Avg. per night